Best Vacation Rentals in North Chatham

Top Vacation Rentals in North Chatham

Plan your perfect getaway with our selection of vacation rentals in North Chatham. Each choice offers a blend of comfort and local charm, ideal for families and groups.

Vacation Rentals in North Chatham
Haddock Hill House
Bed & Breakfast
20 Haddock Hill Road, Old Chatham, NY, NY 12136, USA

Providing a garden, Haddock Hill House provides accommodations in Old Chatham. This property offers access to a terrace, free private parking, and free Wifi. Outdoor seating is also available at the bed and breakfast. Towels and bed linen are featured in the bed and breakfast. The accommodation offers an air conditioning, a heating, and a private bathroom. Guests at Haddock Hill House will be able to enjoy activities in and around Old Chatham, like cycling, fishing, and hiking. The bed and breakfast has a picnic area where you can spend the day outdoors. Tanglewood Musical Center is 18 miles from the accommodation, while Tanglewood is 18 miles away. Albany International Airport is 26 miles from the property.

Guest Reviews:

- "Stunning oasis in Old Chatham, gorgeous en suite with beautiful private garden patio." - "Comfortable, quiet and cozy sums up HHH!" - "excellent" - "Convenient, comfortable spot with beautiful private patio, and lots of space inside." - "We loved the place and hope to return." - "Lovely accommodations!" - "Very nice room. Great bathroom. Comfortable bed.Lovely host" - "A perfect landing pad for our Tanglewood adventure."

Vacation Rentals in North Chatham
Martin Van Buren historical Log cabin
Cabin
Valatie, New York, USA

The Hudson Berkshire Martin VB Log Cabin

This cute historic cabin was the Martin Van Buren hunting lodge back in the day.

The cabin has been completely restored - maintaining the the vibe of the old while incorporating modern

The cabin has an open kitchen with separate dining area and living room - facing an old stone fireplace. There is separate bedroom and bathroom.

The log cabin has a private open-field backyard surrounded by trees - ideal idea breakfast, lunch or even a barbecue.

Amenities:

Bedding/Linens • Child Friendly • Laundry • Pet Friendly • Fireplace/Heating • Internet • Wellness Facilities • Air Conditioner • Security/Safety

Vacation Rentals in North Chatham
Blue Spruce Inn & Suites
Hotel
3093 U.S. 9, Valatie, NY, NY 12184, USA

Located in Valatie, 19 miles from Albany-Rensselaer Amtrak, Blue Spruce Inn & Suites provides accommodations with a garden, free private parking and a shared lounge. The property is around 20 miles from Albany City Hall, 20 miles from Times Union Center and 20 miles from The Egg Center for the Performing Arts. Corning Tower is 21 miles from the motel and University of Albany SUNY is 24 miles away. Guest rooms are equipped with air conditioning, a flat-screen TV with satellite channels, a fridge, a coffee machine, a shower, free toiletries and a desk. With a private bathroom equipped with a bath and a hairdryer, rooms at the motel also offer free WiFi, while selected rooms contain a garden view. Guest rooms include a closet. Guests at Blue Spruce Inn & Suites will be able to enjoy activities in and around Valatie, like hiking. A business center is at guests' disposal at the accommodation. Empire State Plaza Convention Center is 20 miles from Blue Spruce Inn & Suites, while New York State Capitol is 20 miles away. Albany International Airport is 24 miles from the property.

Guest Reviews:

- "Very nice!" - "lovely stay, nice room" - "Love it. Would book again." - "Excellent place to stay would send everyone there!" - "Very peaceful stay." - "Very nice independent motel. Spacious and clean." - "Blue Spruce Inn & Suites exceeded our expectations! We will be back!" - "Wonderful stay ~Thank you" - "simple, very clean, convenient location." - "Great little motel!" - "The location was convenient, traveling west after a concert at Tanglewood."

Vacation Rentals in North Chatham
Majestic Lake Front Chalet
Ski Chalet
Valatie, New York, USA

The modern lake house is newly renovated and is situated on 26 secluded wooden acres with a private lake.

Experience the ultimate retreat at our 2,100 sq ft 2 bedroom, 2.5 bathroom, modern lake front property.

Enjoy swimming, fishing ( catch and release ) free kayaking and paddle boarding on our Private Lake.

Relax and unwind at our Outdoor Fire Pit or simply enjoy the picturesque view out of our floor to ceiling picture windows.

Your Dream Family Reunion at our Secluded 26-acre Property awaits.

We are also open to host a small, QUIET Wedding or similar event ( inquiry)
There is no review yet, it is newly up for str.

Other Information
The property is shared with our 6 other independent cabins, which are also available for rent separately.

The house is separate from the cabins with its own private area and lake front access.

Perfect for large groups who all want independent living space.

Amenities:

Fireplace/Heating • Child Friendly • Internet • Security/Safety • Laundry • Wellness Facilities • Bedding/Linens • Air Conditioner • Barbecue/Outdoor Cooking • Pet Friendly

Vacation Rentals in North Chatham
Old Dutch Inn
Hotel
8 Broad Street, Kinderhook, NY, NY 12106, USA

Located within 22 miles of Albany-Rensselaer Amtrak and 23 miles of Albany City Hall, Old Dutch Inn provides rooms with air conditioning and a private bathroom in Kinderhook. Providing a terrace, the property is located within 23 miles of Times Union Center. New York State Capitol is 23 miles from the inn and Corning Tower is 24 miles away. With a private bathroom equipped with a shower and free toiletries, rooms at the inn also have free WiFi, while selected rooms here will provide you with a city view. At Old Dutch Inn all rooms come with a flat-screen TV with cable channels. You can play pool at the accommodation. The Egg Center for the Performing Arts is 23 miles from Old Dutch Inn, while Empire State Plaza Convention Center is 23 miles away. Albany International Airport is 27 miles from the property.

Guest Reviews:

- "Perfect antidote to chaos is to be found at the stunningly restored Old Dutch Inn"

Vacation Rentals in North Chatham
Camp Kinderhook Lake House
House
Valatie, New York, USA

This house is on a quiet cove on Kinderhook lake. It has been newly renovated within the past two years. And has a great old time camp feel. There is one full bedrooms on the main floor, Downstairs there are also two bedrooms; one with two twin beds and the other with two bunk beds. 2 full bathrooms, one upstairs, one downstairs. This house is about a scenic 2 hour drive from NYC, and about 30 minutes from Albany.Prefect for a weekend getaway. In the winter, nearby Jiminy Peak and Catamount make for a perfect opportunity to ski or snowboard. The house has a full kitchen, and living room. Outside, there is an upper and lower deck, perfect for barbecues and summer fun. Nearby are villages Chatham and Hudson, perfect for antiquing and exploring, with lots of great places to eat. Possible summer activities include kayaking, fishing,hiking and golfing. Good for families looking for a relaxing vacation. Come enjoy all the Hudson Valley has to offer!
NO PETS, NO SMOKING ..Please

Guest Reviews:

- "We really enjoyed our stay at the Kinderhook Lake House. Initially, there was a misunderstanding about water access for swimming; we misunderstood and thought there was land to water access, but you have to take a boat/kayak/other out into the lake and swim from there or a small island, and from there the water is clean and refreshing. The owners were very sweet when we raised our concern about water access and helped us work through it. The house and view are awesome, and we had many enjoyable hours there."

Vacation Rentals in North Chatham
Cozy lake house
House
68 Lake Shore Circle Drive, Nassau, NY, NY 12123, USA

Cozy lake house is located in Nassau, just 14 miles from Albany-Rensselaer Amtrak and 17 miles from Albany City Hall. This property offers access to a balcony, free private parking, and free Wifi. Rensselaer Polytechnic Institute is 17 miles away and Empire State Plaza Convention Center is 17 miles from the vacation home. The spacious vacation home includes 1 bedroom, a fully equipped kitchen with a dishwasher and an oven, as well as a coffee machine. Featuring air conditioning, this unit has a dressing room and a fireplace. The property has an outdoor dining area. Times Union Center is 17 miles from the vacation home, while The Egg Center for the Performing Arts is 17 miles away. Albany International Airport is 22 miles from the property.

Amenities:

Parking • Air Conditioner • Internet • Child Friendly • Security/Safety

Vacation Rentals in North Chatham
Heaven Can't Wait, On Beautiful Kinderhook Lake!
Cottage
Valatie, New York, USA

Hello again repeat and new guests! Thank you for a very enjoyable 2024. All of you were great! We are looking forward to another relaxing season and know you are too! Our cottage is offered to those guests who are looking to relax & enjoy peace & quiet. NO LOUD MUSIC or parties! (Which is not allowed) C Yes, we have Wi - Fi so you can do your computer work while being safe and enjoy the beautiful sunset & other views from inside the cottage, indoor or outdoor porch. We are offering our lovely cottage to those who want to relax and enjoy life from May 1st thru November 15th. The docks and outside deck re stained.
To be fair to all our guests, weekly rentals are from Friday - Friday ( Thank you ) Our cottage is right on beautiful Kinderhook lake. Walk down the porch & the lake is 10' away right off lawn & The Empire State Trail is only 200' away for those who like to bike walk or both and see beautiful scenery including pastures, streams horses and horse farms!
There are kayaks for your use or bring your own kayaks canoes or boats & tie them up to one of the two docks. Fishing is great and you could fish off the dock, porch or front lawn if you wanted to! The house has 2 ac units and a forced hot air heater. There is no better way to relax then to have dinner or just a few cold ones and enjoy the view of the lake. BBQ, table with umbrella, seating for 6 & lounges on outside deck. Also has inside porch with dining table, couch, tv & ac. Less than 2 hrs. from NYC about 45 minutes from Albany, Monticello, so everything is close. It is all ready for a week or weekend getaway with your family & friends, (Just bring your own linens, 1 queen & 1 double bed) or a romantic weekend getaway for u & your special someone. It has a full kitchen, complete with 4 burner stove, oven, full size refrigerator, microwave, all needed cookware, dinner plates for 6, utensils & even a new coffee maker. It sleeps 4 comfortably with 2 bedrooms. It has a full bath with a shower. The Hudson River Rail Trail is nearby!! So come and relax and enjoy. Thank you in advance for looking. Just a heads up to our guests that the lake gets lowered around October 15th so fishing, kayaking and swimming will not be available. Don't worry the views are still beautiful and you can still see the water. Thank you again, John

Guest Reviews:

- "Clean and very comfortable cottage at the water's edge. We had a great time kayaking, enjoying the deck and watching the wildlife, visiting Hudson and Chatham and taking walks. Thanks, John!" - "Had a nice three night stay at this cottage on the lake Host communicated well, and we enjoyed our stay Pet friendly location right on the water of Kinderhook lake, can walk from the grass into the lake and the lake is about 4 feet deep out about 100 feet. Some rocks near the shore, bring water shoes."

Vacation Rentals in North Chatham
Cozy lake house
House
68 Lake Shore Circle Drive, Nassau, NY, NY 12123, USA

Cozy lake house is located in Nassau, just 14 miles from Albany-Rensselaer Amtrak and 17 miles from Albany City Hall. With quiet street views, this accommodation features a patio. There's an outdoor fireplace and guests can use free Wifi and free private parking. Featuring a terrace and lake views, the spacious vacation home includes 1 bedroom, a living room, flat-screen TV, an equipped kitchen, and 2 bathrooms with a walk-in shower and a bidet. Featuring air conditioning, this unit has a dressing room and a fireplace. The property has an outdoor dining area. Guests at the vacation home will be able to enjoy activities in and around Nassau, like fishing and hiking. Times Union Center is 17 miles from Cozy lake house, while The Egg Center for the Performing Arts is 17 miles from the property. Albany International Airport is 22 miles away.

Amenities:

Air Conditioner • Child Friendly • Guest Services • Other • Internet • Sports/Activities • Fireplace/Heating • Parking • Security/Safety • Balcony/Terrace

Vacation Rentals in North Chatham
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!
House
Valatie, New York, USA

Welcome to this beautiful lake-front home on Kinderhook Lake, NY.

Totally rebuilt in 2018, this home is designed to maximize the incredible view of the lake. Cool and sunny in the summer, and warm and cozy in the winter. Come and enjoy Lake Kinderhook!!

Located minutes off the NY Thruway and I-90, this property is convenient to the Berkshires, the Hudson River Valley, and several ski areas. Open floor plan, brand new kitchen flows into spacious living area. Huge windows highlight lake front view. Two large bedrooms upstairs, one bedroom on the first floor, plus a comfortable futon in a common area. Plenty of room for sleeping and relaxing. Two bathrooms, one with private entrance into the Master bedroom. Large lakeside yard with dock. If you have a boat/trailer, there is a grass/gravel boat launch immediately adjacent to the property. Reasonably quiet lake, some motor boat activity, but most is on the far side of the lake.

Summertime note: We love the lake, but so do bugs. All windows have screens, but please keep doors shut to prevent insects from entering. They actually camp out like little mercenaries waiting to ambush every time the door opens.

PLEASE VERIFY NUMBER OF GUESTS IN PARTY WHILE BOOKING— base rates are for parties of FOUR, any additional are $40/per person, per night up to a grand total maximum of SIX guests.

For your protection and ours, outdoor security cameras are present covering the entrances to the property. No interior security/monitoring devices exist inside the home.

Jiminey Peak — 30 minutes Hunter Mountain — 1.5 hrs Gore Mountain — 1.5 hrs Mt. Snow— 1.5 hrs Hudson, NY — 30 min Berkshire’s— 45 min Tanglewood— 40 min

Guest Reviews:

- "We had a wonderful visit to Kinderhook Lake. The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed the 3 kayaks and swimming off the small dock. We also enjoyed chatting with our neighbors a bit. Thanks for a great visit!" - "Great property! Nice lake views in a comfortable home. Everything you would want to enjoy the water - kayaks, life jackets, fishing poles. Outdoor fire pit on the water is a relaxing spot to sit at any time. Beautiful and peaceful mornings sitting in Adirondack chairs on the water. Will stay again in the future!"

Vacation Rentals in North Chatham
Farmhouse Retreat, Outdoor Dining, Fire-Pit, Fast Wifi, Golf and 3-Acre Privacy
House
379 County Route 28B, Valatie, NY, NY 12184, USA

Farmhouse Retreat, Outdoor Dining, Fire-Pit, Fast Wifi, Golf and 3-Acre Privacy offers accommodations in Valatie, 19 miles from Times Union Center and 19 miles from The Egg Center for the Performing Arts. With free private parking, the property is 18 miles from Albany-Rensselaer Amtrak and 19 miles from Albany City Hall. Empire State Plaza Convention Center is 19 miles away and New York State Capitol is 19 miles from the vacation home. With free Wifi, this 1-bedroom vacation home provides a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation has a fireplace. Guests at the vacation home will be able to enjoy activities in and around Valatie, like fishing and hiking. Guests can also relax in the garden. Corning Tower is 20 miles from Farmhouse Retreat, Outdoor Dining, Fire-Pit, Fast Wifi, Golf and 3-Acre Privacy, while University of Albany SUNY is 23 miles away. Albany International Airport is 24 miles from the property.

Amenities:

Sports/Activities • Guest Services • Internet • Air Conditioner • Security/Safety • Pet Friendly • View • Parking • Barbecue/Outdoor Cooking • Other • Child Friendly

Vacation Rentals in North Chatham
A 200 year old center hall colonial between the Berkshires and the Hudson River
Cottage
Old Chatham, New York, USA

This property is located on an acre in a small village within easy walking distance of a gourmet country store, a tavern, and the post office. As you can see from the photos, this is a true family home with an up-to date fully equipped kitchen, a formal dining room, comfortable living room with a library of books, and many cozy spaces to enjoy.

NEARBY: An easy drive to Tanglewood, Jacob’s Pillow, Hancock Shaker Village, the Norman Rockwell Museum, the Red Lion Inn, Chesterwood, historic Berkshire “cottages” such as Naumkeg and the Mount, the Berkshire Botanical Gardens, Kripalu, the Appalachian Trail, Olana, Hudson’s antique stores, the area’s fresh produce markets, and the Shaker Museum.. It’s a fun day trip to racing at Saratoga, to Mass MoCA, and to the Clark Museum.
The house features a new entrance and mudroom at the rear of the driveway. Downstairs the house consists of a large living room, a formal dining room, big eat-in kitchen, laundry room, a sun porch, the mudroom, and a full bath.
Upstairs there are two bedrooms, one with a half bath. The house comfortably sleeps 4. One bedroom has a double bed, the other, one double bed and a single. The sun porch on the first floor has a trundle bed which is great for napping. The porch, however, is usable only in the summer as it is not heated. Each upstairs bedroom has a window air-conditioner in summer.
In the living room there is a fireplace, and a TV with Apple TV. The fully equipped kitchen includes a microwave, dishwasher, a Sub Zero refrigerator, a gas stove, and all cooking utensils and tableware. The formal dining room seats eight. There is a washer and a dryer in the laundry room off the kitchen. All bed and bath linens, as well as table linens, are provided. The house is WIFI enabled.

Guest Reviews:

- "Timeless,elegant country home with screened porch and large yard. The house was comfortable and perfect for our family of five and dog. It was a short drive to Tanglewood, in a sleepy corner just down the road from Chatham. Our host provided all the needed information as well as recommendations in the area." - "In town for my high school reunion. Wish we could have stayed longer. House was perfectly remodeled, very thoughtful. We had everything we needed. Old Chatham is quaint little town. Liked listening to the creek across the road."

Vacation Rentals in North Chatham
Stylish Farm Stay • Swimmable Pond • Pet Friendly
House
Nassau, New York, USA

Summary:
Escape to serenity on a peaceful 134-acre estate with a modern farmhouse beside a private pond. Perfect for extended stays, remote work, or family time, this retreat offers fast Wi-Fi, a gourmet kitchen, cozy fireplace, and outdoor delights like a grill, patio, and fire pit. Secluded yet close to everything—your upstate escape awaits.

The Space:
🏡 The Space – Modern Comfort Meets Rustic Calm
This waterfront farmhouse is tucked beside a large pond and surrounded by open skies and quiet trails. Inside, you’ll find:

🛋️ Interior Features:
- Open floor plan with radiant heated floors
- Gourmet kitchen with gas stove, large fridge, and full cookware
- Wood-burning fireplace for cozy evenings
- Complimentary Netflix, coffee station, and mini bar
- Washer/dryer for extended stays
- Abundant parking

🌿 Outdoor Amenities:
- Spacious patio and front porch
- Grill with table and umbrella
- Fenced backyard for pets
- Pond with fishing, kayaking, and swimming

Whether you're sipping coffee at sunrise or winding down by the fire pit, this home invites you to slow down and reconnect.

Guest Access:
🔑 Guest Access – Yours to Enjoy

Guests have full access to:
- The entire farmhouse
- The swimmable pond and surrounding property
- Outdoor amenities including patio, grill, and fire pit
- Free parking on-site

✨ Looking for more space? This home is part of a 134-acre estate with four unique homes—including two tiny homes and a main house with a pool. All can be booked together for retreats, reunions, or multi-family escapes.

The Neighborhood:
🌄 The Neighborhood – Hudson Valley Charm
Located in Nassau, NY—just a short drive from Kinderhook and Hudson—this area is beloved by artists, writers, and weekenders from NYC and Boston. It’s where quiet country roads meet vibrant village life.

🗺️ Nearby Highlights:
- 10 min to Kinderhook’s historic village, galleries, and cafés
- 15 min to Hudson’s boutiques, breweries, wine bars, and antique shops
- Local farm stands, apple orchards, nature preserves, and scenic drives
- Cultural gems like The School (Jack Shainman Gallery) and Hudson Hall
- Easy access to the Empire State Trail for biking and hiking
- MVP Arena & Palace Theatre

Whether you're exploring the region or staying in, the location offers the best of both worlds.

Getting Around:
🚗 Getting Around – Peaceful, Yet Connected
A car is recommended to explore the area’s hidden gems, but everything is within easy reach. Drive scenic backroads to nearby towns, or hop on the Amtrak in Hudson for a direct line to NYC.

🚗 Transportation Highlights:
- Free parking on-site
- 15 min to Hudson Amtrak Station
- Easy drives to Kinderhook, Chatham, and Albany
- Ride-sharing services available in the area

Other Things to Note:
🎶 Other Things to Note – Beyond the Countryside
This region offers more than just quiet charm—it’s a cultural and recreational hub.

🏟️ Local Highlights Include:
- Art galleries, wine bars, and farm-to-table dining in Hudson
- Historic architecture and weekend markets in Kinderhook
- Seasonal festivals, antique fairs, and live performances
- Scenic golf courses and nature preserves
- Proximity to colleges like Bard, SUNY Albany, RPI, HVCC and Columbia-Greene

🏇 Saratoga Highlights:
- The legendary Saratoga Racecourse, hosting summer meets and iconic events like the Travers Stakes
- Saratoga Performing Arts Center (SPAC), featuring concerts, ballet, and festivals year-round
- Seasonal events like Chowderfest, farmers markets, and antique fairs

🏢 Nearby Employers & Business Hubs:
- Regeneron Pharmaceuticals, a major biotech company headquartered in East Greenbush
- Amazon Distribution Centers and logistics hubs within driving distance
- GlobalFoundries, a leading semiconductor manufacturer in Malta, NY

🏛️ Albany, NY – Capital City Charm & Culture
Just 20 minutes from Nassau, Albany offers a mix of history, arts, and nature:
- New York State Capitol – A stunning architectural landmark with guided tours and rich political history
- Empire State Plaza – Home to The Egg performing arts center, reflecting pools, and seasonal events
- Washington Park – Designed by the same architect as NYC’s Central Park, with walking trails and the Tulip Festival in spring
- Albany Institute of History & Art – One of the oldest museums in the U.S featuring Hudson River School paintings and regional artifacts
- USS Slater – A WWII destroyer escort turned floating museum on the Hudson River
- MVP Arena & Palace Theatre – Hosting concerts, comedy shows, and sporting events year-round

Whether you're here for a weekend escape, a seasonal stay, or a remote work retreat, this location offers the perfect balance of tranquility and access to everything that makes the Hudson Valley and Capital Region so magnetic.

Interaction with Guests:
🤝 Interaction with Guests – Here When You Need Us
We respect your privacy and want your stay to feel effortless. While we don’t interact unless needed, we’re always just a message away if you have questions or need assistance. Whether it’s a local tip or a quick fix, we’re here to help—quietly and promptly.

Guest Reviews:

- "It is a beautiful property with so much fun for little kids. Mine never wanted to leave. It made for a very memorable trip. I would highly recommend staying here." - "All good!" - "There isn't much to add to all the other 5 star reviews. We agree that the farmhouse is clean and comfortable with all the necessary amenities. We especially enjoyed the rainfall shower in the master bath. I nicknamed it little niagra. The donkeys are super cute! Grab one of the brushes hanging by the gate and give them a good grooming - they will love you for it! The large pond in front of the house is deep and clear, perfect for swimming, with just enough weeds to make for good bass fishing. My daughter and I fished almost every evening. It was a great way for us to bond one last time before she heads off to college. There are tons of really good places to eat nearby. Our favorite meal was takeout from Golden Harvest Farms ."

Vacation Rentals in North Chatham
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.
Apartment
Nassau, New York, USA

Step back in time into a fully appointed apartment in a stately1830 Federal Home.
Rest Haven Estate is a country manor with a wonderful history that only adds to its charm.
Private entrance to suite located on the second floor. Full kitchen, bath, large living room with 2 twin sofa sleepers, cozy private bedroom with queen bed. High speed internet. Cable TV, Microwave, Stove, Refrigerator, Desk, Coffee Maker
Located across from Albany- Hudson Electric Trail for walking, biking, cross country skiing, and snow shoeing. Convenience shops walking distance. Pizza sub shop on same block. Ice Cream shop around the corner.

Guest Reviews:

- "We had a wonderful stay in this historic house and were overwhelmed with the kindness and generosity of our hosts. If we are ever in the area again, we will book again!" - "We were quite happy with our stay in this lovely apartment. The listing is quite accurate. Our host obviously spent much time making it comfortable and supplied the necessities we would need. Although the bedroom was quite small, it was cozy." - "Beautiful home in a quaint little town. Love the feel of these tony little places in upstate NY."

Vacation Rentals in North Chatham
Tiny Home Escape • Swimmable Pond • WiFi • Pets OK
Apartment
Nassau, New York, USA

Summary:
Where City Stress Fades and Country Calm Begins
Tucked into the rolling countryside of Nassau, NY, this cozy retreat offers the perfect blend of rustic charm and modern comfort—just minutes from Kinderhook and Hudson. Whether you're escaping the city for a weekend or settling in for a creative recharge, this peaceful haven is ideal for couples, solo travelers, or small families. Surrounded by nature and culture, it’s a favorite among NYC and Boston second-home seekers for good reason.

The Space:
🏡 The Space – Cozy, Clean, and Full of Character
Step into a thoughtfully curated space that feels both grounded and inspiring. Whether you're curled up with a book or sipping wine under the stars, this home invites you to slow down and savor the moment.

🛋️ Inside Features:
- Comfortable bedroom(s) with plush bedding and calming décor
- Open living area with natural light and cozy seating
- Fully equipped kitchen with essentials for cooking and coffee
- Clean, modern bathroom with fresh towels and toiletries
- High-speed Wi-Fi and smart TV for streaming or remote work

🌳 Outdoor Highlights:
- Peaceful front patio for morning coffee or evening stargazing
- Scenic views of the surrounding countryside
- Easy access to hiking trails, farm stands, and local markets

Whether you're here to write, rest, or reconnect, this space is designed to support your rhythm.

Guest Access:
🔑 Guest Access – Yours to Enjoy

Guests have full access to the entire home, including:
- All bedrooms, bathrooms, kitchen, and living spaces
- Outdoor areas for lounging or dining
- Free parking on-site
- Self-check-in for ease and privacy
- Everything is set up for a seamless, stress-free stay—just arrive and unwind.

✨ Planning a group getaway or special event? This home is part of a 130-acre estate with four separate homes, all available to rent together for a truly unforgettable experience. Perfect for multi-family vacations, retreats, or celebrations, booking the entire property offers space, privacy, and a one-of-a-kind setting in the heart of the Hudson Valley.

The Neighborhood:
🌄 The Neighborhood – Hudson Valley Charm
Located in Nassau, NY—just a short drive from Kinderhook and Hudson—this area is beloved by artists, writers, and weekenders from NYC and Boston. It’s where quiet country roads meet vibrant village life.

🗺️ Nearby Highlights:
- 10 min to Kinderhook’s historic village, galleries, and cafés
- 15 min to Hudson’s boutiques, breweries, wine bars, and antique shops
- Local farm stands, apple orchards, nature preserves, and scenic drives
- Cultural gems like The School (Jack Shainman Gallery) and Hudson Hall
- Easy access to the Empire State Trail for biking and hiking
- MVP Arena & Palace Theatre

Whether you're exploring the region or staying in, the location offers the best of both worlds.

Getting Around:
🚗 Getting Around – Peaceful, Yet Connected
A car is recommended to explore the area’s hidden gems, but everything is within easy reach. Drive scenic backroads to nearby towns, or hop on the Amtrak in Hudson for a direct line to NYC.

🚗 Transportation Highlights:
- Free parking on-site
- 15 min to Hudson Amtrak Station
- Easy drives to Kinderhook, Chatham, and Albany
- Ride-sharing services available in the area

Other Things to Note:
🎶 Other Things to Note – Beyond the Countryside
This region offers more than just quiet charm—it’s a cultural and recreational hub.

🏟️ Local Highlights Include:
- Art galleries, wine bars, and farm-to-table dining in Hudson
- Historic architecture and weekend markets in Kinderhook
- Seasonal festivals, antique fairs, and live performances
- Scenic golf courses and nature preserves
- Proximity to colleges like Bard, SUNY Albany, RPI, HVCC and Columbia-Greene

🏇 Saratoga Highlights:
- The legendary Saratoga Racecourse, hosting summer meets and iconic events like the Travers Stakes
- Saratoga Performing Arts Center (SPAC), featuring concerts, ballet, and festivals year-round
- Seasonal events like Chowderfest, farmers markets, and antique fairs

🏢 Nearby Employers & Business Hubs:
- Regeneron Pharmaceuticals, a major biotech company headquartered in East Greenbush
- Amazon Distribution Centers and logistics hubs within driving distance
- GlobalFoundries, a leading semiconductor manufacturer in Malta, NY

🏛️ Albany, NY – Capital City Charm & Culture
Just 20 minutes from Nassau, Albany offers a mix of history, arts, and nature:
- New York State Capitol – A stunning architectural landmark with guided tours and rich political history
- Empire State Plaza – Home to The Egg performing arts center, reflecting pools, and seasonal events
- Washington Park – Designed by the same architect as NYC’s Central Park, with walking trails and the Tulip Festival in spring
- Albany Institute of History & Art – One of the oldest museums in the U.S featuring Hudson River School paintings and regional artifacts
- USS Slater – A WWII destroyer escort turned floating museum on the Hudson River
- MVP Arena & Palace Theatre – Hosting concerts, comedy shows, and sporting events year-round

Whether you're here for a weekend escape, a seasonal stay, or a remote work retreat, this location offers the perfect balance of tranquility and access to everything that makes the Hudson Valley and Capital Region so magnetic.

Interaction with Guests:
🤝 Interaction with Guests – Here When You Need Us
We respect your privacy and want your stay to feel effortless. While we don’t interact unless needed, we’re always just a message away if you have questions or need assistance. Whether it’s a local tip or a quick fix, we’re here to help—quietly and promptly.

Guest Reviews:

- "The property was fantastic. We felt close to off the grid while on the property. Absolutely beautiful and peaceful!" - "The outdoors around the house are fantastic, from the lawn, to the pond, to the trails, and the multiple outside sitting places. The house itself is great, very practical, comfortable beds. The indoors are definitely more of a base-of-operations as opposed to a place for an inside staycation. Kitchen is totally functional, but not for indoor cooking a big meal. Had toaster, microwave, and stove top, but no oven. Nice outdoor grill."

Vacation Rentals in North Chatham
Hudson: Martin Van Buren 2 bedroom lake house cottage
Cottage
Valatie, New York, USA

Four saison cottage
If you are a nature lover and like comfort then this place is for you.

Former home of the Martin Van Buren hunting lodge and more recently, the Hudson Boys Club.

26 private acres with 1500 ft of lakefront: swimming, kayaking and fishing - bring your fishing rod! You might be lucky and catch a good bass!

1150 sf bungalow w/ 200 sf patio (ideal for eating out!). Open loft style living: bedroom, living room, kitchen and dining. 2 bedroom and 2 bathrooms.

The property have in total 6 cottage , for a 16 guest max , can also host weddings, events, price upon request.
Thank you .

Guest Reviews:

- "We had a great time. The air conditioning was great and needed as we had hot and humid weather. We took a swim in the lake which was accessible from a floating dock. Instructions were accurate and provided some local suggestions. Close to a supermarket and farm stands." - "Wonderful property close to everything. Would definitely stay there again." - "Great in every respect." - "Great place. We will be back." - "I had such a fabulous stay at this property! Beautiful lakeside setting. The home itself is perfectly designed. It has absolutely everything you would need to relax and recharge. I can't say enough about the design and the amenities. You will not be disappointed! I did not want to leave. I hope to be back again soon!"

Vacation Rentals in North Chatham
Hudson: Martin Van Buren lake cottage IIII (4)
Cottage
Valatie, New York, USA

Four season cottage
If you are a nature lover and like comfort then this place is for you.

Former home of the Martin Van Buren hunting lodge and more recently, the Hudson Boys Club.

26 private acres with 1500 ft of lakefront: swimming, kayaking and fishing - bring your fishing rod! You might be lucky and catch a good bass!

400 sf bungalow w/ 200 sf patio (ideal for eating out!). Open loft style living: bedroom, living room, kitchen and dining.

The property can also host weddings, events, price upon request.

Guest Reviews:

- "Lots of amenities to enjoy including the well stocked kitchen, beautiful deck with chaise recliners, patio table and chairs, games, a charcoal grill, and, of course, the lake! The bed is also very comfortable. Walking down to the water takes about 2 minutes. The grassy area in front of the water has tons of Adirondack chairs, fire pits, paddle boards and kayaks to use. There’s a small dock to jump off of. We reached out to the hosts several times and each time they were very response, once even driving up to bring us an extra game. We grilled, played croquet and bocce (included!), and enjoyed the lake. There are 5 cabins in a row (you can see the neighbors decks) and a larger house coming online soon. This would be an awesome spot for a family reunion or gathering of friends."

Vacation Rentals in North Chatham
Tiny Home Escape • Swimmable Pond • WiFi • Pets OK
Apartment
Nassau, New York, USA

Summary:
Where City Stress Fades and Country Calm Begins
Welcome to our charming lakefront tiny home—just 2 hours from NYC and Boston, yet worlds away in peace and simplicity. Nestled on a private peninsula with a sandy shoreline, this pet-friendly retreat offers everything you need for a cozy weekend or extended stay.

Please note: Screens previously shown on the patio have been removed to maintain a pet-friendly environment. The space remains perfect for morning coffee or sunset drinks.

The Space:
🏡 The Space – Tiny in Size, Big on Comfort
Featured on HGTV, this thoughtfully designed tiny home sleeps 4 comfortably and is ideal for couples, solo travelers, or small families. Guests often say they wish they’d booked a longer stay—and we agree.

🛏️ Sleeping Arrangements:
- Master loft with queen bed
- Guest loft with queen bed

🛋️ Living & Kitchen:
- Cozy living area with couch and bar seating
- Pocket doors open fully to the deck for seamless indoor-outdoor flow
- Fully stocked kitchen with electric cooktop, refrigerator drawers, Subzero beverage fridge, microwave, toaster, Keurig, and all cookware essentials

🚿 Bathroom:
- Full bathroom with stand-up shower and fresh towels

🎬 Extras:
- Wi-Fi
- Plenty of parking

Central location near highways, breweries, restaurants, colleges, and major employers

Guest Access:
🔑 Guest Access – Yours to Enjoy

Guests have full, private access to the tiny home, including:
- Waterfront deck and patio
- Spring Fed Pond access for swimming and fishing
- Trails for walking, biking, and jogging
- Kitchen, living space, and sleeping lofts
- Free parking and self-check-in

✨ Planning a group getaway or special event? This home is part of a 130-acre estate with four unique homes, all available to rent together. Book the entire property for a one-of-a-kind experience—perfect for retreats, reunions, or multi-family escapes.

The Neighborhood:
🌄 The Neighborhood – Hudson Valley Charm
Located in Nassau, NY—just a short drive from Kinderhook and Hudson—this area is beloved by artists, writers, and weekenders from NYC and Boston. It’s where quiet country roads meet vibrant village life.

🗺️ Nearby Highlights:
- 10 min to Kinderhook’s historic village, galleries, and cafés
- 15 min to Hudson’s boutiques, breweries, wine bars, and antique shops
- Local farm stands, apple orchards, nature preserves, and scenic drives
- Cultural gems like The School (Jack Shainman Gallery) and Hudson Hall
- Easy access to the Empire State Trail for biking and hiking
- MVP Arena & Palace Theatre

Whether you're exploring the region or staying in, the location offers the best of both worlds.

Getting Around:
🚗 Getting Around – Peaceful, Yet Connected
A car is recommended to explore the area’s hidden gems, but everything is within easy reach. Drive scenic backroads to nearby towns, or hop on the Amtrak in Hudson for a direct line to NYC.

🚗 Transportation Highlights:
- Free parking on-site
- 15 min to Hudson Amtrak Station
- Easy drives to Kinderhook, Chatham, and Albany
- Ride-sharing services available in the area

Other Things to Note:
🎶 Other Things to Note – Beyond the Countryside
This region offers more than just quiet charm—it’s a cultural and recreational hub.

🏟️ Local Highlights Include:
- Art galleries, wine bars, and farm-to-table dining in Hudson
- Historic architecture and weekend markets in Kinderhook
- Seasonal festivals, antique fairs, and live performances
- Scenic golf courses and nature preserves
- Proximity to colleges like Bard, SUNY Albany, RPI, HVCC and Columbia-Greene

🏇 Saratoga Highlights:
- The legendary Saratoga Racecourse, hosting summer meets and iconic events like the Travers Stakes
- Saratoga Performing Arts Center (SPAC), featuring concerts, ballet, and festivals year-round
- Seasonal events like Chowderfest, farmers markets, and antique fairs

🏢 Nearby Employers & Business Hubs:
- Regeneron Pharmaceuticals, a major biotech company headquartered in East Greenbush
- Amazon Distribution Centers and logistics hubs within driving distance
- GlobalFoundries, a leading semiconductor manufacturer in Malta, NY

🏛️ Albany, NY – Capital City Charm & Culture
Just 20 minutes from Nassau, Albany offers a mix of history, arts, and nature:
- New York State Capitol – A stunning architectural landmark with guided tours and rich political history
- Empire State Plaza – Home to The Egg performing arts center, reflecting pools, and seasonal events
- Washington Park – Designed by the same architect as NYC’s Central Park, with walking trails and the Tulip Festival in spring
- Albany Institute of History & Art – One of the oldest museums in the U.S featuring Hudson River School paintings and regional artifacts
- USS Slater – A WWII destroyer escort turned floating museum on the Hudson River
- MVP Arena & Palace Theatre – Hosting concerts, comedy shows, and sporting events year-round

Whether you're here for a weekend escape, a seasonal stay, or a remote work retreat, this location offers the perfect balance of tranquility and access to everything that makes the Hudson Valley and Capital Region so magnetic.

Interaction with Guests:
🤝 Interaction with Guests – Here When You Need Us
We respect your privacy and want your stay to feel effortless. While we don’t interact unless needed, we’re always just a message away if you have questions or need assistance. Whether it’s a local tip or a quick fix, we’re here to help—quietly and promptly.

Guest Reviews:

- "After so many nights spent pouring over tiny houses online and watching every HGTV show on the subject, this cozy little place answered the call. We arrived from the airport late so we didn’t know what to expect driving in. The property was easy to find and the Alice in Wonderland style signs were so cute and easy to follow - even at almost midnight after a day of traveling from the west coast. The wooded path to The Tiny House is a little bouncy but when you come out into the clearing you’ve entered another world. It was too dark to realize the magnitude of our surroundings but the adorable house stood ready to welcome us. When we got up the next morning we were absolutely awestruck by the lake and forrest views out of every window. Bed linens, mattresses and pillows were soft and we slept like logs. We couldn’t find extra blankets but we didn’t look very hard. We took advantage of the well appointed kitchen as well as the bbq and fire pit outside. There are canoes and pedal boats as well as a crazy trampoline float in the middle of the lake! This is not the right stay for you if you are looking for long luxurious showers (the small water tank is clearly noted in the incredibly thorough house manual) but if you want all the joys of the outdoors while staying conveniently located to the city, this is the most unbelievably lovely option."

Vacation Rentals in North Chatham
Cozy Cottage in the Woods
Cottage
Brainard, New York, USA

The Cottage is an idyllic private one-bedroom cottage nestled in the woods. The place is equipped with a private queen-sized bedroom; if you need extra room, there is a full-sized pull-out couch in the living room. A fully equipped kitchen, dining area, and bathroom with a tub and shower exist. Columbia County is the perfect retreat for hikers, hunters, fly fishers, or people who want to relax and unwind and star gaze at night by the fire pit. With a lot to see and do nearby, the Hamlet of Old Chatham, Chatham Village, and East Greenbush offer plenty to do. Lots of hiking. Also, Hancock Shaker Village in Hancock, Massachusetts, is just 15 miles/24 km away. Just a 30-minute drive to Tanglewood, MA, or a 27-minute drive to Jiminy Peak or Bosquet Ski Resorts, or enjoy the quiet, and bright evening sky. The hosts live full-time in the main house. No Smoking or Pets.

Guest Reviews:

- "Beautiful property, thoughtful and comfortable design and furnishings, hosts could not have been more welcoming, warm and helpful. Terrific stay in every way!" - "Hands down the best Vrbo stay we ever experienced. The property was well maintained and very peaceful as it’s tucked in a wooded area. The hosts were very welcoming and attentive, especially at check in with a small charcuterie to accompany a chilled bottle of wine after a long day of traveling. The only problem is that we didn’t get to spend enough time there."

Vacation Rentals in North Chatham
Hudson: Martin Van Buren lake cottage lll (3)
Cottage
Valatie, New York, USA

Four season cottage
If you are a nature lover and like comfort then this place is for you.

Former home of the Martin Van Buren hunting lodge and more recently, the Hudson Boys Club.

26 private acres with 1500 ft of lakefront: swimming, kayaking and fishing - bring your fishing rod! You might be lucky and catch a good bass!
400 sf bungalow w/ 200 sf patio (ideal for eating out!). Open loft style living: bedroom, living room, kitchen and dining.
The property can also host weddings, events , price upon request.
There is a pet fee : $30 per pet/ per day

Guest Reviews:

- "The spot was a great relaxing escape from the city. We were up here for a bike ride, and this was the perfect spot to come back to after a day of riding. " - "Such a beautiful, peaceful getaway to be surrounded by nature, but also accessible to so many charming small towns. We can't wait for our future stay. Also loved how dog friendly the property was. Highly recommend staying here!!!!"

North Chatham Family Friendly Vacation rentals

North Chatham Vacation rentals with Parking

North Chatham Pet Friendly Vacation rentals

North Chatham Vacation rentals with Entertainment

North Chatham Vacation rentals with Private Pool

North Chatham Vacation-Rentals on the Map

Compare the Best Vacation-Rentals in North Chatham – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Haddock Hill House 20 Haddock Hill Road, Old Chatham, NY, NY 12136, USA 150 3.0 8.2 12 Click here
Martin Van Buren historical Log cabin Valatie, New York, USA 221 2.0 1 Click here
Blue Spruce Inn & Suites 3093 U.S. 9, Valatie, NY, NY 12184, USA 115 2.0 8.3 197 Click here
Majestic Lake Front Chalet Valatie, New York, USA 540 2.0 1 Click here
Old Dutch Inn 8 Broad Street, Kinderhook, NY, NY 12106, USA 292 1.0 10.0 4 Click here
Camp Kinderhook Lake House Valatie, New York, USA 312 10.0 104 Click here
Cozy lake house 68 Lake Shore Circle Drive, Nassau, NY, NY 12123, USA 267 9.5 2 Click here
Heaven Can't Wait, On Beautiful Kinderhook Lake! Valatie, New York, USA 242 9.8 89 Click here
Cozy lake house 68 Lake Shore Circle Drive, Nassau, NY, NY 12123, USA 297 9.5 2 Click here
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views! Valatie, New York, USA 534 10.0 56 Click here
Farmhouse Retreat, Outdoor Dining, Fire-Pit, Fast Wifi, Golf and 3-Acre Privacy 379 County Route 28B, Valatie, NY, NY 12184, USA 550 1 Click here
A 200 year old center hall colonial between the Berkshires and the Hudson River Old Chatham, New York, USA 321 10.0 34 Click here
Stylish Farm Stay • Swimmable Pond • Pet Friendly Nassau, New York, USA 321 9.8 29 Click here
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite. Nassau, New York, USA 115 10.0 26 Click here
Tiny Home Escape • Swimmable Pond • WiFi • Pets OK Nassau, New York, USA 284 9.6 25 Click here
Hudson: Martin Van Buren 2 bedroom lake house cottage Valatie, New York, USA 288 9.4 12 Click here
Hudson: Martin Van Buren lake cottage IIII (4) Valatie, New York, USA 218 10.0 11 Click here
Tiny Home Escape • Swimmable Pond • WiFi • Pets OK Nassau, New York, USA 372 10.0 7 Click here
Cozy Cottage in the Woods Brainard, New York, USA 157 10.0 6 Click here
Hudson: Martin Van Buren lake cottage lll (3) Valatie, New York, USA 218 10.0 4 Click here

Note: The prices for each Vacation-Rentals in North Chatham do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Vacation rentals in North Chatham that include a pool include:

  • Private Estate • Pool • Pets • Nature Trails.- Review Count: 3, Rating: 9.4
  • Amazing 5 Star Estate! FREE Gift Card to Wellness Center included w/your stay!.- Review Count: 3, Rating: 10.0
  • Luxury 134-Acre Retreat • 4 Homes • Pool • Pond.- Review Count: 0, Rating: 0.0

Family-friendly vacation rentals in North Chatham include:

  • Haddock Hill House.- Review Count: 12, Rating: 8.2
  • Martin Van Buren historical Log cabin .- Review Count: 0, Rating: 0.0
  • Blue Spruce Inn & Suites.- Review Count: 197, Rating: 8.3

Pet-friendly vacation rentals in North Chatham include:

  • Martin Van Buren historical Log cabin .- Review Count: 0, Rating: 0.0
  • Blue Spruce Inn & Suites.- Review Count: 197, Rating: 8.3
  • Majestic Lake Front Chalet .- Review Count: 0, Rating: 0.0

Vacation rentals in North Chatham with private or on-site parking include:

  • Haddock Hill House.- Review Count: 12, Rating: 8.2
  • Blue Spruce Inn & Suites.- Review Count: 197, Rating: 8.3
  • Camp Kinderhook Lake House.- Review Count: 104, Rating: 10.0

Some of the best Vacation Rentals in North Chatham are:

  • Haddock Hill House.- Review Count: 12, Rating: 8.2
  • Blue Spruce Inn & Suites.- Review Count: 197, Rating: 8.3
  • Martin Van Buren historical Log cabin .- Review Count: 0, Rating: 0.0

Some of the popular Vacation Rentals in North Chatham are:

  • Blue Spruce Inn & Suites.- Review Count: 197, Rating: 8.3
  • Camp Kinderhook Lake House.- Review Count: 104, Rating: 10.0
  • Heaven Can't Wait, On Beautiful Kinderhook Lake!.- Review Count: 89, Rating: 9.8