Best Vacation Rentals in Madison

Top Vacation Rentals in Madison

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

Vacation Rentals in Madison
The Homestead
Bed & Breakfast
391 Boston Post Road, Madison, CT, CT 06443

The Homestead offers accommodations in Madison, 18 miles from Yale University and 20 miles from The Yale Bowl. 13 miles from Thimble Islands and 18 miles from City Hall, the property features free bikes and a garden. There's a sun terrace and guests can make use of free Wifi, free private parking, and an electric vehicle charging station. At the bed and breakfast, units include a wardrobe, a flat-screen TV, a private bathroom, bed linen, and towels. All units are equipped with air conditioning, and some units at the bed and breakfast have a patio. The rooms are equipped with heating facilities. A selection of options including warm dishes, local specialities, and fresh pastries are available for the buffet breakfast. There is a snack bar and lounge. Guests can also warm up near the outdoor fireplace after a day of cycling. Wesleyan University is 22 miles from the bed and breakfast, while Goodspeed Opera House is 25 miles from the property. Tweed-New Haven Airport is 16 miles away.

Guest Reviews:

- "Exceptional, one of the nicest and most creatively thought out places we have every visited." - "The most tranquil, serene, experience! Can't wait to bring my family back!" - "An Unexpected Treat!" - "This is truly a pet-friendly haven, your home away from home!" - "Heaven on earth!" - "Cozy and welcoming Inn near the Seashore" - "Everything you could possibly need" - "We didn’t want to leave!" - "Amazing! Highly recommend."

Vacation Rentals in Madison
Madison Beach Hotel
Hotel
94 West Wharf Road, Madison, CT, 06443, USA

Beachfront hotel with full-service spa
Spend the day relaxing on Madison Beach Hotel's private sand beach or pampering yourself at the hotel's full-service spa.
Madison Beach Hotel offers 32 accommodations with minibars and laptop-compatible safes. Beds feature Egyptian cotton sheets, down comforters, and premium bedding. Flat-screen televisions come with premium digital channels and pay movies. Refrigerators and coffee/tea makers are provided. Bathrooms include bathrobes, designer toiletries, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wired and wireless Internet access. Business-friendly amenities include desks and desk chairs, as well as phones; free local calls are provided (restrictions may apply). Additionally, rooms include safes and complimentary bottled water. A nightly turndown service is provided and housekeeping is offered daily.


Recreational amenities at the hotel include a private beach and a fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "What made Madison Beach Hotel's beautiful property really stand out for us is its stellar customer service. Every single staff member my H and I encountered was friendly and eager to offer assistance. On our last night we enjoyed a delicious dinner overlooking the Long Island sound and had a waiter who could not have been more gracious. We look forward " - "Toilet in room did not work which is excusable at this price point. Needed new plunger mechanism which is ridiculous given what I paid for room. Everything else was outstanding."

Vacation Rentals in Madison
Madison Beach Hotel, Curio Collection by Hilton
Hotel
94 W Wharf Rd, Madison, CT, CT 06443-2905, USA

The Hotel is located adjacent to the Long Island Sound in Madison, Connecticut. The hotel is located between New York City and Boston, Massachusetts. The hotel has private beach access, full-service restaurant, valet parking, and WiFi. Each room has a TV. All rooms are fitted with a private bathroom equipped with a shower. There is a 24-hour front desk at the property. Waterbury is 30 mi from Madison Beach Hotel, Curio Collecti, while East Hampton is 30 mi from the property. The nearest airport is Bradley Airport, 47 mi from Madison Beach Hotel, Curio Collection by Hilton.

Guest Reviews:

- "Very beautiful room" - "Wedding weekend. Perfect spot for celebrations" - "A relaxing and calming stay." - "A must stop on the CT shore!" - "We loved the entire trip." - "Luxurious, classy, entire staff phenomenal. Returning again. Telling everyone" - "Overall, an excellent break from daily routines." - "We had a great time at the hotel , the location is great !" - "It’s a beautiful spot with lovely rooms and decent food. Just wish the beach area was a bit larger so all guests can e"

Vacation Rentals in Madison
Renovated 1 bedroom Cozy Apt-Madison
Apartment
Madison, Connecticut, USA

Fully renovated 1 bed , 1 bath, 650 APARTMENT. Walk to surf club beach in Madison and bike to town center. This is a 2nd floor unit with tons of light. Comes with all the comforts like linens, Keurig, glass shower, tasteful furniture, WIFI, Cable etc. Apartment is located in a carriage house on a 1.2 acres estate property. There is a washer /dryer in the foyer of carriage house to use. There is a private deck off the kitchen to enjoy table and chairs with a sitting area. The stone patio below on ground level has a grill and table and chairs to enjoy. All utilities are included for extended stay. There are 2 bikes for renters to use. We are also a stones throw from Madison golf course, Madison Beach Hotel, Town Green and downtown shopping is a walk or bike away. This Unit is 2nd floor with two entrances, one with a keypad. There is a parking lot area for carriage house and this unit has up to two spaces.

in summer. Prefer a one month minimum but would consider 2 week duration.

Guest Reviews:

- "Beyond my family’s expectations. Renovated unit including new furniture, towels and linens, plus an outdoor gas grill and bicycles. The location is within walking or biking distance of the beach (down a private lane adjacent to the carriage house), town and Madison Beach Hotel. We walked a couple times to the Madison Beach Hotel to have drinks, dinner and watch the evening sunset – very relaxing. Madison is the quintessential New England town with a variety of restaurants and stores to keep you busy. Finally, I can’t say enough about the hosts. Great people who were friendly, accommodating and made my family feel right at home. I wouldn’t hesitate to recommend a stay at this unit."

Vacation Rentals in Madison
Scranton Seahorse Inn
Bed & Breakfast
818 Boston Post Road, Madison, CT, CT 06443

Scranton Seahorse Inn in Madison provides accommodations with a garden and a terrace. Both free Wifi and parking on-site are accessible at the bed and breakfast free of charge. The accommodation offers airport transfers, while a car rental service is also available. Some accommodations include a patio and a cable flat-screen TV with DVD player, CD player as well as air conditioning and heating. At the bed and breakfast, units come with a private bathroom. As an added convenience, Scranton Seahorse Inn offers packed lunches for guests to bring on excursions and other trips off-property. The area is popular for cycling and hiking, and bike rental is available at this 4-star bed and breakfast. The bed and breakfast has a picnic area where you can spend the day outdoors. Hammonasset Beach is 1.6 miles from the accommodation, while Thimble Islands is 15 miles from the property. Tweed-New Haven Airport is 18 miles away.

Guest Reviews:

- "A great stay in Madison!" - "We will definately return" - "Our night at the Inn was exceptional, with excellent accommodations and a fabulous breakfast in the morning." - "Very nice B&B in a great location with an excellent host." - "Seahorse is Comfortable and peaceful sanctuary"

Vacation Rentals in Madison
The Scranton Seahorse Inn
Bed & Breakfast
818 Boston Post Road, Madison, CT, 06443, USA

Bed & breakfast in Madison with a full-service spa and free breakfast
This smoke-free bed & breakfast features a full-service spa, a meeting room, and concierge services. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, dry cleaning, laundry facilities, and a library are onsite.
The Scranton Seahorse Inn offers 7 air-conditioned accommodations with DVD players and bathrobes. Beds feature premium bedding. Flat-screen televisions come with cable channels. This Madison bed & breakfast provides complimentary wireless Internet access. Housekeeping is provided daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Beautiful! " - "Perfection 💕 I had such a great time. Michael was a great host. Traveling solo I felt very safe. If you are looking for a quiet and safe place to lay your head down, definitely do not pass this place up. Breakfast was luxurious. I will most definitely book this place again. I had a great time. " - " Wry clean and quiet. Very comfortable." - "Nice quaint quiet property. " - "Great place great owners" - "Amazing experience!"

Vacation Rentals in Madison
2 Mi to Dtwn 2-Acre Retreat with Large Yard!
House
Madison, CT, USA

2 Mi to Dtwn 2-Acre Retreat with Large Yard! offers accommodations in Madison, 22 miles from The Yale Bowl and 22 miles from Goodspeed Opera House. The property is around 16 miles from Thimble Islands, 20 miles from City Hall, and 20 miles from Yale University. Free Wifi is available throughout the property and Hammonasset Beach is a 14-minute walk away. The air-conditioned vacation home is composed of 3 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 3 bathrooms. Towels and bed linen are provided in the vacation home. The property has an outdoor dining area. Wesleyan University is 22 miles from the vacation home, while Connecticut Post Mall Shopping Center is 28 miles away. Tweed-New Haven Airport is 18 miles from the property.

Amenities:

Child Friendly • Parking • Other • Fireplace/Heating • Security/Safety • Guest Services • Accessibility • Internet

Vacation Rentals in Madison
The Homestead
Bed & Breakfast
391 Boston Post Rd, Madison, CT, 06443, USA

Beach bed & breakfast with a nearby private beach and free breakfast
Along with a snack bar/deli, this smoke-free bed & breakfast has free use of bicycles and express check-out. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, wedding services, a garden, and a lobby fireplace are onsite.
Housekeeping is available on request.
The Homestead offers 10 air-conditioned accommodations with complimentary bottled water and hair dryers. Each accommodation is individually furnished and decorated. Memory foam beds feature Egyptian cotton sheets, down comforters, and premium bedding. 36-inch Smart televisions come with premium cable channels and Netflix.

Bathrooms include showers. This Madison bed & breakfast provides complimentary wireless Internet access. Hypo-allergenic bedding, irons/ironing boards, and change of towels can be requested. Housekeeping is provided on request.


Recreational amenities at the bed & breakfast include complimentary bicycles.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Fabulous, uniquely decorated B&B with accommodating hosts. Luxurious beds and bedsheets, corner to corner squeaky clean. Will definitely return." - "This is a very charming B&B. Staff and owners were great. Very friendly and accommodating. Rooms were clean and well appointed; very clean; nice firm beds and selection of pillows. Will definitely stay again." - "Great people and accommodations " - "Great area , Great people,"

Vacation Rentals in Madison
Waterfront home surrounded by stunning water views.
House
Madison, Connecticut, USA

Stunningly updated waterfront beach house. Water access best for boating, kayaking and paddle boarding! Never leave the house or venture out in town. Located in charming Madison, CT. Close to adorable downtown, local beaches and Hammonassett state park/beach! Home has 3 bedrooms and 1 bath. Window unit air conditioning.

Guest Reviews:

- "Can't get closer to the ocean than this! I wanted a quiet cottage on the beach for a couple of relaxing evenings. This house was the perfect answer. The porch sits 10ft off the water's edge. The opposite side is steps away from open marsh. Open a window on both sides of the house for instant ocezn breeze. Well stocked. Great place for a couple, or a family with kids. Very close to Madison and Guilford town areas. " - "Had a perfect short stay. It was absolutely adorable and amazing views. The neighbors were all so friendly and helpful. An unexpected perk! Perfect spot to sit in a beach chair reading while listening to the ocean sounds! Just so peaceful and happy!"

Vacation Rentals in Madison
Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town
Apartment
Madison, Connecticut, USA

Birdsong is a handicap accessible apartment, which is attached to the west side of our house with beautiful views of the sunsets. We have 2 acres of land with lush gardens and a waterfall and lily pond. The cathedral ceiling apartment, with plenty of natural light, has an open floor plan of a living room, dining area and kitchen with a separate bedroom. The bedroom has a queen size bed with California closets, while the bathroom has a handicap accessible shower and sink. In the kitchen you will find everything you will need to create your own favorite meals. Have breakfast, lunch or dinner on the terrace in this tranquil setting, while listening to the waterfall of the pond. A gas grill is available for use.

The town of Madison, which is located on Long Island Sound, is a perfect destination for relaxing an exploring. Centrally located - New York City is 2 hours away while Boston is 2 ½ and New Haven twenty minutes. The train from the downtown station will connect you with all of these destinations, but why leave the quaint town of Madison. Stroll through the town center and you will find an Cinema, the renowned RJ Julia ‘s independent bookstore, coffee shops, a cheese shop, International and American restaurants, boutiques, a library, outdoor sculpture by nationally renowned artists and a large grocery store.
Joining us for the summer? As is typical of New England towns, there is a green in town, where you will find concerts, a farmer’s market, arts and crafts fairs and antique shows from May through September. On the 4th of July weekend, join the local fun watching the parade, relaxing at the Pops summer concert and watching the fireworks.
Madison’s beaches, as well as, Hammonasset State Park (beach), have playgrounds, tables and grills for picnicking, sports fields and bocce/pétanque courts. (We will provide the pétanque balls.)
There are trails throughout town where you can hike and a nature center for birding and learning about the local animals.
There are a myriad of things to do for those cool or rainy days. You might decide to follow the Impressionist or the wine trial throughout Connecticut, or you might visit one of the many museums, go shopping (there are 2 Outlet Centers within a 20 minute drive), go to the theater, listen to live music or visit one of the gambling casinos.

Guest Reviews:

- "Great scenery all around. Peaceful place to stay yet close enough to everything you need for a fun trip to the coast of CT." - "The accommodations at Birdsong were spacious, comfortable & exceptionally clean! We were greeted by our hosts Kathleen & Dean, who gave us a tour & showed us everything we needed to know to make our stay as smooth as possible. We had delicious scones, wine, & beautiful flowers upon our arrival - we enjoyed the outdoor patio with the humming birds & lovely flowering landscape. Beach chairs , towels, umbrella & beach pass were available for us to use during our stay - there were lots of great restaurants nearby. Kathleen & Dean responded quickly to any questions we had throughout our weekend. It was so quiet & relaxing. We are looking forward to staying at Birdsong again soon! Trish & Bill"

Vacation Rentals in Madison
Direct waterfront renovated cottage.
Cottage
Madison, Connecticut, USA

Newly renovated cottage. Direct waterfront home in Madison’s most desirable waterfront area. Four bedrooms, 2 full and one 1/2 bath. Outdoor private shower. Sleeps 7. Walk to the Madison beach hotel and into town (restaurants, shops, grocery store, cvs, starbucks) or along Madison’s beautiful coastline. Bike to hammonaset state park along the green mile trail. Beautiful green lawn from your deck to the Long Island sound. At low tide, there is sand between our seawall and rock outcroppings where you can walk & put a chair & enjoy the sunshine. There also is a sandy beach (regardless of the tide) approximately 6 homes away that you can use. See photos. There is room for 6 cars to park on rock driveway. Enjoy all Madison has to offer from the best view in town. Short walk to Madison Beach Hotel for outdoor/indoor dining , spa and entertainment. Also, a short walk to Madison Beach Club and Madison Country Club which are for members only.

Air conditioning units in June, July & August. One ac unit is based for family room and dining room. All three upstairs bedrooms have ceiling fans and will have individual AC units. There is no heat in the cottage. April & October can be chili, but beautiful! There is a wall heater that heats the family room and dining area.

Guest Reviews:

- "Everything was great! - our second time renting this house with an amazing view of the sound from the porch; relaxing for the entire family. Construction on new home going on next-door was a little annoying, but that will end someday. Otherwise our family had a great time and the host Bryan was very organized and considerate." - "Lovely spot, kind owner, summer breezes and sun. Thanks!" - "We had the best weekend away at this cozy (and uber clean!) cottage with the most stunning view. The kids loved splashing in the water and we loved the peace and quiet."

Vacation Rentals in Madison
New Madison beach house - Ocean front- Great views- booking Summer 2025
House
Madison, Connecticut, USA

Searching for the perfect getaway? Look no further than our home on the Madison shoreline, where a private beach and the Long Island Sound are your front yard! It’s perfect for a weekend getaway or the family vacation of a lifetime — in summer AND the winter.

Every room in our home has breathtaking views. Whether it’s the sight of the sun rising over the Long Island Sound, or the view of the Neck River trickling along behind the house, you’ll understand why people say that a picture is worth a thousand words. Every window in the house is broad, to provide the perfect view, and storm-resistant.

The first floor is "open concept" with a family room, kitchen, dining area, and study. Our front deck is made of Azek and expands the width of the home for views of Falkner’s Island and Long Island Sound. We placed a rock barrier around our private beach for protection and during high tide, the water creates a private pool.

The kitchen comes fully stocked with a microwave, oven, dishwasher, dishes, pots and pans, baking sheets, Keurig K-cup coffee machine, toaster, cutting boards, utensils, glasses, mugs, and platters. There are the basics to get you started, including dish soap, toilet paper, dishwasher tablets, cleaning supplies and paper towels.
The dining area has a table with 6 chairs, though it can comfortably seat 10. We have four additional chairs available in storage.

The master bedroom has a queen size bed, luxury linens, a full closet, dresser, ceiling fan, and TV. The first window overlooks the water and one of the best views of the Long Island Sound. Every morning, you will wake up to one of the most beautiful sunrises in the world. The guest room has a queen size bed, ceiling fan, a roomy closet, and has an ocean facing window.

The second guest room has one full bed and one twin bed. The third guest room comes with a bunk bed that sleeps two – perfect for the young kids in your family!

The house also comes with fresh linens on all the beds and bath towels for your use.

One of my family’s favorite things to do is walk to Guilford’s iconic Red Shack through Grass Island. This scenic stroll takes you through a beautiful nearby beach and is just a mile away from the house. The boat launch is also found on this path.

Madison’s downtown area is 3.5 miles from the home. There you will find restaurants, coffee shops, the famous R.J. Julia bookstore, art galleries, cinema, unique shops, and other essentials. Drive ten minutes to outlet stores or to the Shoreline East Train that will take you to Grand Central Station, New York. Nearby tourist attractions include Thimble Island tours, Thimble Island Brewing Co Stony Creek Brewery, Chamard Vineyards, pick your own fruits at Bishop's Orchards, Mystic Seaport and Aquarium, Submarine Force Museum in Groton, Essex Steam Train and Riverboat Ride and Hammonasset Beach State Park. Our home is also located just 4.5 miles from historic downtown Guilford. Their town center is incredibly walkable and has a variety of restaurants, from Thai to traditional New Haven pizza, for you and your family to enjoy.

At our home, you will be able to enjoy the quiet serenity of a private beach while being a short drive away from New Haven and other shoreline communities. We hope that you will create some wonderful memories, as we have, at this home.
Please see below a video from the town of Madison
https://www.elocallink.tv/m/v/Redesign4/?pid=w6wpB7z3&fp=ctmadi24_wel_iwd#c|ctmadi24_tour_iwd

We have installed exterior cameras for your safety.

Please note that this house is available to book only on VRBO.

Guest Reviews:

- "We had an incredible stay in Madison. The location was perfect - right on the beach and close to nearby towns. The house was comfortable and well stocked with everything we needed. The beach was perfect and great for our young son who could play in the protected area behind the rocks. Joe was incredibly responsive and helpful throughout our stay." - "Everything about this beach house is spectacular! We traveled with 2 adults & 3 children. Everyone had an amazing time at the house. Very clean, excellent communication with the host, amazing views from all rooms, quiet private beach. I could go on and on about with raving reviews. Do not hesitate booking the beach house. My family and I look forward to future stays!!!"

Vacation Rentals in Madison
Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd
House
Madison, Connecticut, USA

2 Bedroom, 1 & 1/2 Bath year round house in the scenic and classic New England town of Madison, CT on Long Island Sound. A 550 foot walk to private LI Sound Beach as shown in Photos. House is also located on the Western edge of Hammonasset Beach State Park. Our house, at 7 Pent Road, is on a very private, quiet, dead end lane, in a family neighborhood just off Webster Point Road. Madison is in the heart of the Connecticut 'Gold Coast', a series of small sea shore New England towns where Boating, Beaches, Swimming, and Restaurants are all in abundance.

Day trips to Providence Rhode Island, Old Essex CT, Yale/New Haven and Mystic Aquarium are among the local venues. Contact owner for approval if your pet is over 20 pounds or have more than 1 pet. See fees for cleaning and pet charges. The 2 BRs are on the 2nd floor, and the stairway is narrow; - there is a day bed in the sun room. Parking is limited to 2 vehicles, max vehicle size is mini van. For November thru April academic rentals - 1) the rentals are a minimum of 120 days, 2) renter pays all utilities in addition to the rental rates. 3) Cleaning, Pet fees, and Security Deposit amount will be based on duration. The house color has been updated FROM BLUE TO CAPE COD GRAY.

Guest Reviews:

- "So close to everything I am looking for in a summer retreat—an uncrowded beach just a walk away, a short bike ride to downtown treats (a hometown cinema, ice cream parlor and fantastic bookstore to name a few) with shoreline views along the way! That's why I return year after year." - "Once again my grandson and I stayed at this property for a week this summer. We loved the short walk to the beach. The house was great for the two of us. The neighborhood is quiet and friendly. Gene was very accommodating. It was easy to book online. I did recommend it to other people looking for a beach rental."

Vacation Rentals in Madison
Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio
House
Madison, Connecticut, USA

Gorgeous, modern, beach farmhouse is waiting for you to come and enjoy! This fully renovated home has access to a private beach just 4 houses away! Open floor plan with high ceilings makes this home a retreat. This home offers 3 bedrooms, 1 full bathroom, ceiling fans, central air conditioning and an outdoor, private shower. The home has a fenced in bluestone patio with an outdoor kitchen with built in gas grill and a wood burning fire pit. There is an outdoor table with 4 dining chairs, Adirondack chairs and umbrellas.

The kitchen comes fully stocked with a microwave, oven, dishwasher, dishes, pots and pans, baking sheets, Keurig K-cup coffee machine, toaster, cutting boards, utensils, glasses, mugs and platters. There are the basics to get you started including dish soap, toilet paper, dishwasher tablets, cleaning supplies and paper towels. There is a table and 5 chairs in the breakfast nook.

Master bedroom has a queen size bed, luxury linens, full closet, 2 dressers, ceiling fan and TV. First guestroom has a full size bed, Pottery Barn bedding, closet and ceiling fan. Second guestroom has full size bed, Pottery Barn bedding, full closet and ceiling fan. The house also comes with fresh linens on all of the beds and bath towels for your use.

Living room has TV, board games, ceiling fan, vaulted ceilings, couch, 2 overstuffed chairs and 2 Chippendale chairs. The home also has WIFI.

Basement has a full size washer and dryer for your convenience.

Beach chairs, cooler, sand toys, kayak, boogie boards, Razor scooters and beach umbrellas are all available for your use. 4 beach towels are also provided for your convenience. You can literally just pack you flip flops and bathing suits an arrive!

We provide a guide book to allow you to have the most comfortable and enjoyable stay. We have 2 driveways which is rare for a shore home.

3 minute drive to downtown Madison, Surf Club, the Madison Beach Hotel, shops and restaurants.

Stroll along the beach to fish or walk to the Madison Surf Club to enjoy a large playground, snack bar and public beach. Walk or bike into the town of Madison where you will find restaurants, coffee shops, the famous R.J. Julia bookstore, art galleries, cinema, unique shops and other essentials. Drive ten minutes to outlet stores or to the Shoreline East Train that will take you to Grand Central Station, New York. Nearby tourist attractions include Thimble Island tours, Thimble Island Brewing Co Stony Creek Brewery, Chamard Vineyards, pick your own fruits at Bishop's Orchards, Mystic Seaport and Aquarium, Submarine Force Museum in Groton, Essex Steam Train and Riverboat Ride and Hammonasset Beach State Park. Our home is located just 2 miles from historic downtown Madison and 3.5 miles from downtown Guilford.

*** We kindly ask that you remove your shoes before entering the home and wash sand off of feet in the outdoor shower.

*** Important! Please shake off sand from bathing suits, towels and clothes before putting them in washing machine. The washing machine pump cannot handle sand and will seize if there is too much sand in the laundry.

There is also a hose in the outside shower for your convenience, and we would kindly ask you to rinse off outside before coming in.

Guest Reviews:

- "Cozy, warm home, beautifully decorated.Has everything you need! Location was great for us. Only a very short walk to the beach. Highly recommend!" - "Ideal location! This is a lovely home in a quiet and walkable coastal neighborhood, close to beaches and restaurants. The house is clean, comfortable and well furnished. Highly recommend!" - "A quiet, cozy, modern, house with quality throughout in a quiet, beautiful small community, in a beautiful New England town with lots to do and (heaven for me) a pizza spot (Grand Apizza)) owned by the Nuzzo family of New Haven pizza fame!"

Vacation Rentals in Madison
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Apartment
Madison, Connecticut, USA

Come stay on the closest property to Hammonasset Beach State Park in all of Madison! Just 1 mile and your feet are on the beach, with two miles of white sandy beach to relax, explore, and enjoy.

Walk across the street to the Greenway Trail and stroll the scenic mile of gorgeous marsh and ocean views leading to the beach, or head just 1.5 miles into downtown Madison for shops, restaurants, and charm.

This peaceful 1.5-acre property includes two rentals:

There is the main house and the this fully renovated, modern carriage house apartment — located just 50 feet from the main home but fully private.

The apartment features:
• Private entrance
• Fully equipped kitchen
• Outdoor deck and fire pit
• Separate patio with dining area
• Beautiful yard surrounded by trees

The entire space is yours. The only shared space is the driveway.

Whether you're here for a romantic beach getaway or a quiet coastal retreat, you’ll love the privacy, location, and charm of this hidden gem. Book your stay today and enjoy the best of beachside Madison!

Guest Reviews:

- "My husband and I stayed here with our 3 month old infant while visiting family in the area. We brought our own crib and baby supplies but besides that the property had everything we needed and was really clean, comfortable and nicely decorated. Would definitely recommend to others." - "This place is exactly as described. Was absolutely perfect, cozy, and comfortable. Thanks Kevin!" - "I’ll be returning here whenever there’s no room to stay at Mom’s house. Immaculate, light-filled rooms with comfy new furniture, bedding — what a treat. The kitchen has everything you might need and the host has provided basic items that will please dog-owners and “I forgot to pack X” packers. The location is a stone’s throw from the beach and a nice walk into charming downtown Madison."

Vacation Rentals in Madison
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
House
Madison, Connecticut, USA

Experience a combination of spectacular marsh and water views along with designer inspired finishes. Kayak out to the Long Island Sound or enjoy the sun rising over the marsh among the Great Blue Herons.

We are committed to making your stay peaceful and easy, whether you're a writer looking for new inspiration or a small group looking to explore the marsh and everything else this beautiful shoreline town has to offer. Featuring 2 well positioned bedrooms at opposite ends of the house with living and laundry rooms in between it makes for a larger feel and it's DIRECTLY on the water. A twin alcove bunk allows for an additional sleeping option with direct water views, a great place for someone to perch and keep an eye on all of the nature outside the wall of windows as the sun comes up.

Ice cool air conditioning in the summer and cozy heat in the winter!

Smart TVs throughout the house allow you to bring your favorite apps with you along with high-speed fiber optic internet service, you can keep in touch with the office from a place that feels Far Farrr away.

Don't worry about getting your clothes dirty on your new adventures. A washer and dryer are located next to the kitchen for your convenience!

In addition to the brand-new kitchen stocked with all the basics don't forget to add some grilling items to the Instacart order or take a trip to Clinton and experience the new impressive Big Y grocery store. We have a Webber grill mounted on the deck off of the kitchen!

We have lived and visited the river house for years now and not one of those days have we forgot to comment in awe of the views. Having access to such a Gem of a property is something we are happy to share with you and look forward to helping build lasting memories for years to come.

Guest Reviews:

- "Gorgeous views in a comfortable, hassle free setting." - "We really enjoyed our stay at this cute home. Everything was clean, decor was charming, and a perfect fit for our family to relax. The house is more spacious than it might appear in photos. The area is quiet and near plenty of beaches, restaurants, and shops on the shoreline." - "The River House is the perfect retreat for a relaxing and quiet new england getaway. Piscuesque river views, and newly renovated. We enjoyed our mornings with the beautiful birds, turtles, and crabs. We had everything needed and the it was spotless. I emailed questions a few times to Hunter and always received a timely response. He was super helpful with restaurant suggestions, and upon arrival after asking if there were beach chairs and an umbrella we were pleasantly surprised to have 4 brand new chairs and an umbrella on the front porch. We really appreciated the extra efforts and his care for his guests. Great location,very private, and tucked away but within 5-10 mins to any conveniences needed. Without a doubt, I would recommend this darling river house cottage for a relaxing shoreline vacation. Thank you Hunter for allowing us create a weeknd full of wonderful memories for me and my family."

Vacation Rentals in Madison
Ideal Madison home just steps to the beach
House
Madison, Connecticut, USA

Sleeps 8 - Fabulous summer rental in the heart of Madison, CT, this 2,741 sq ft 4-bedroom home is perfect for a family vacation. Located only a 100 yards from the beach and minutes from beautiful downtown Madison. Steps from the Madison Beach Hotel that offers spa services and 5-star dining. This updated home features a large eat-in gourmet kitchen, ideal for family entertainment. Features hot water outdoor shower, patio area, air conditioning, Tesla charger, and much more.

Minimum 4 nights - July & August are minimum monthly stays.

Home is located on a small, private road in a quiet neighborhood. Parking is limited to property which can accommodate a maximum of 3 vehicles in driveway. Large gatherings are not allowed.

Guest Reviews:

- "We stayed for four nights with family for an end of summer getaway. There are four good size bedrooms and the sitting room off the master is a huge amount of additional space. In our case, this was a perfect area for our 9 month olds crib. The house came equipped with just about anything you could need and a grocery store is just minutes away in town! The beach is a very short walk and Surf Club beach is only about 1/2 mile. I recommend Christie’s, which is steps away, for breakfast! Overall, communication was great and a wonderful experience overall."

Vacation Rentals in Madison
4 bedroom - steps to sandy beach in perfect location!
House
Madison, Connecticut, USA

Location, location, location! Less than 2 minute walk to sandy private town beach. A rare find in the quaint beachside town of Madison, CT, this updated year round beach house is a perfect location for you to hear the waves, smell the salt air and walk to the beach. This spacious, newly renovated house has 4 bedrooms (Master Bedroom located on the first floor), 2 remodeled baths, remodeled kitchen with granite and stainless steel appliances and is charmingly and tastefully furnished. Complete with an expansive screened in sun porch, an outdoor shower, plenty of outdoor seating for entertaining, private lot and plenty of parking, it is perfect for you and your guests. Sleeps up to 9. AC units in windows for summer rental and complete with Comcast Gigabit Service with Orbi Mesh Network, perfect for multiple video calls and gaming at the same time.

Located only 100 yards from a life-guarded beach on the Long Island Sound, it is also only 1/2 mile from the center of town, renowned for its historic town green, world class bookstore, art cinema and restaurants. It’s a perfect location to relax and enjoy all that Madison has to offer.
You can easily make day trips to Mystic Seaport, the Yale campus in New Haven, the Thimble Islands, Essex and other Connecticut River Towns, Vineyards and Shopping Outlets. We are located approximately 30 minutes from New Haven and 40 minutes from Mystic Seaport, Mystic Aquarium and Resort Casinos (Foxwoods and Mohegan Sun). Other nearby attractions include Hammonasset State Park, the Goodspeed Opera House and Essex Steam Train. Shop and dine in the quaint neighboring towns of Guilford, Branford, Old Lyme and Old Saybrook…all only minutes away.

Weekly rentals available, 2 weeks preferred

Guest Reviews:

- "Beautiful home, close to the beach, close to the town and GREAT communication with the owners. We are sorry we forgot to sign your book when we were leaving. We thoroughly enjoyed our stay. Thank you for making our vacation wonderful." - "We had a great time. What a beautiful home with exceptional location!" - "East Wharf is it’s own friendly little community within Madison great for that early coffee all the way through to sunset. Madison is a very safe town so kids can ride their bikes for a famous Ashley’s ice cream or go to one of America’s few remaining independent book shops, R J Julia. Beautiful beach walks along the coast and you can be back at the house from the beach in minutes. House is a fun combo of a more classic beach house with lots of modern touches like the gas fire pit which we used every night, and a big outdoor shower which everyone used."

Vacation Rentals in Madison
Beautiful Beach Home and Garden Paradise
House
Madison, Connecticut, USA

Beautifully designed and Remodeled Beach home and 1/2 acre native garden paradise with incredible views of Long Island Sound and steps away from a sandy private association beach. This is a perfect place to unwind, connect with nature and enjoy time with family or friends.

Guest Reviews:

- "This place is awesome with great beach access, ocean view, nice neighborhood, 2 patios, and wonderful kitchen & bedrooms. Owner was very helpful and accessible by text all the time!" - "Wonderful home in a lovely beach neighborhood. Great views from the living room window. Plenty of spaces for our family to spread out. We will be back!!" - "A fantastic home to gather in. The kitchen was fully equipped, if you like to cook we highly recommend this rental. Right off the LI sound, a super relaxing location with views of the sunrise . Would love to stay again."

Vacation Rentals in Madison
Newly-renovated beach house; steps to water; walk to town!
House
Madison, Connecticut, USA

Exceptional beach house with all the trimmings in a family neighborhood steps away from the East Wharf beach, ranked by Save the Sound as one of the best swimming beaches in CT. The home is complete with all the amenities including outdoor shower, awesome patio with a firepit and a large yard, and newly renovated bathrooms with heated floors. Enjoy walking, biking and rollerblading along the shoreline.
A short walk to downtown Madison, described as 'a hidden gem of a beach resort in Connecticut that offers a taste of Nantucket much closer to home.' Madison offers shopping, dining, ice cream shops, an independent movie cinema and RJ Julia bookstore, voted by PENN as the best in the Country. Madison's Town Green holds weekly farmer's market, summer concerts, antique shows and flea markets. It’s also home to Hammonasset Beach State Park with a two-mile sandy stretch of beach. Day trips to Providence, Newport,Rhode Island, Essex Ct Yale/NewHaven, Mystic Seaport and Aquarium to name a few local attractions.
PETS ARE ALLOWED FOR AN ADDITIONAL FEE. SLEEPS 6-8.

Guest Reviews:

- "For our family needs it was a perfect size house. The location couldn’t be better to get to the neighborhood beach. We love spending our evenings on the patio around the fire pit. The only thing I can say in the negative comment is the house furniture and various floor elevations were not conducive for older people to sit in or walk around without full attention." - "This was a great spot for our family, it was clean, spacious, close to the beach and into town and Cynthia was very easy to communicate with which made it easy! I could always stay in Madison longer."

Madison Family Friendly Vacation rentals

Madison Vacation rentals with Parking

Madison Vacation rentals with Entertainment

Madison Pet Friendly Vacation rentals

Madison Vacation rentals with Spa

Madison Vacation rentals with Private Pool

Madison Vacation rentals with Private Beach

Madison Vacation-Rentals on the Map

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

Property Name Address Price ($) Star Rating Review Count Book
The Homestead 391 Boston Post Road, Madison, CT, CT 06443 331 4.0 9.8 105 Click here
Madison Beach Hotel 94 West Wharf Road, Madison, CT, 06443, USA 281 4.0 9.4 337 Click here
Madison Beach Hotel, Curio Collection by Hilton 94 W Wharf Rd, Madison, CT, CT 06443-2905, USA 510 4.0 9.5 44 Click here
Renovated 1 bedroom Cozy Apt-Madison Madison, Connecticut, USA 198 4.0 10.0 2 Click here
Scranton Seahorse Inn 818 Boston Post Road, Madison, CT, CT 06443 258 4.0 9.5 43 Click here
The Scranton Seahorse Inn 818 Boston Post Road, Madison, CT, 06443, USA 299 3.0 9.0 236 Click here
2 Mi to Dtwn 2-Acre Retreat with Large Yard! Madison, CT, USA 451 3.0 1 Click here
The Homestead 391 Boston Post Rd, Madison, CT, 06443, USA 330 3.0 10.0 87 Click here
Waterfront home surrounded by stunning water views. Madison, Connecticut, USA 991 2.0 10.0 7 Click here
Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town Madison, Connecticut, USA 190 10.0 86 Click here
Direct waterfront renovated cottage. Madison, Connecticut, USA 691 10.0 84 Click here
New Madison beach house - Ocean front- Great views- booking Summer 2025 Madison, Connecticut, USA 815 10.0 68 Click here
Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd Madison, Connecticut, USA 358 9.4 58 Click here
Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio Madison, Connecticut, USA 498 10.0 41 Click here
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn Madison, Connecticut, USA 356 10.0 36 Click here
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison! Madison, Connecticut, USA 239 9.8 30 Click here
Ideal Madison home just steps to the beach Madison, Connecticut, USA 841 10.0 28 Click here
4 bedroom - steps to sandy beach in perfect location! Madison, Connecticut, USA 782 9.8 25 Click here
Beautiful Beach Home and Garden Paradise Madison, Connecticut, USA 843 10.0 19 Click here
Newly-renovated beach house; steps to water; walk to town! Madison, Connecticut, USA 969 10.0 18 Click here

Note: The prices for each Vacation-Rentals in Madison 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 Madison that include a pool include:

  • New Madison beach house - Ocean front- Great views- booking Summer 2025.- Review Count: 68, Rating: 10.0

Vacation rentals in Madison offering shuttle or transport options include:

  • Scranton Seahorse Inn.- Review Count: 43, Rating: 9.5

These vacation rentals in Madison provide spa or wellness access:

  • Madison Beach Hotel.- Review Count: 337, Rating: 9.4
  • Madison Beach Hotel, Curio Collection by Hilton.- Review Count: 44, Rating: 9.5
  • The Scranton Seahorse Inn.- Review Count: 236, Rating: 9.0

Family-friendly vacation rentals in Madison include:

  • The Homestead.- Review Count: 105, Rating: 9.8
  • Madison Beach Hotel.- Review Count: 337, Rating: 9.4
  • Madison Beach Hotel, Curio Collection by Hilton.- Review Count: 44, Rating: 9.5

Pet-friendly vacation rentals in Madison include:

  • The Homestead.- Review Count: 105, Rating: 9.8
  • Scranton Seahorse Inn.- Review Count: 43, Rating: 9.5
  • Waterfront home surrounded by stunning water views. .- Review Count: 7, Rating: 10.0

Vacation rentals in Madison that include breakfast options include:

  • The Homestead.- Review Count: 105, Rating: 9.8
  • Madison Beach Hotel, Curio Collection by Hilton.- Review Count: 44, Rating: 9.5
  • Scranton Seahorse Inn.- Review Count: 43, Rating: 9.5

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

  • The Homestead.- Review Count: 105, Rating: 9.8
  • Madison Beach Hotel.- Review Count: 337, Rating: 9.4
  • Madison Beach Hotel, Curio Collection by Hilton.- Review Count: 44, Rating: 9.5

Some of the best Vacation Rentals in Madison are:

  • Madison Beach Hotel.- Review Count: 337, Rating: 9.4
  • The Homestead.- Review Count: 105, Rating: 9.8
  • Madison Beach Hotel, Curio Collection by Hilton.- Review Count: 44, Rating: 9.5

Some of the popular Vacation Rentals in Madison are:

  • Madison Beach Hotel.- Review Count: 337, Rating: 9.4
  • The Scranton Seahorse Inn.- Review Count: 236, Rating: 9.0
  • The Homestead.- Review Count: 105, Rating: 9.8