Discover Charming B&Bs in Great Barrington, MA

Wainwright Inn offers accommodations in Great Barrington, 14 miles from Tanglewood Musical Center and 14 miles from Tanglewood. 9.3 miles from Norman Rockwell Museum and 13 miles from Cranwell Spa & Golf Club, the property offers a garden and a terrace. The bed and breakfast also features free Wifi, free private parking, and facilities for disabled guests. Some accommodations include a balcony and a seating area with flat-screen TV, as well as air conditioning and heating. At the bed and breakfast, some units are allergy-free. À la carte and American breakfast options with fresh pastries, pancakes, and fruit are available each morning at the bed and breakfast. Skiing, cycling, and hiking are possible within the area, and Wainwright Inn offers ski storage space. Great Falls is 12 miles from the accommodation, while Canaan Village Historic District is 12 miles from the property. The nearest airport is Bradley International Airport, 51 miles from Wainwright Inn.

- "Exceeded our expectations. Breakfast was delicious and bed very comfortable" - "Our stay was comfortable and pleasant." - "Thanks to Chris and Barb, I'm looking forward to staying there again!" - "Very enjoyable time with everything we needed and more. Would definitely stay there again."

Bed & breakfast with free parking, in the vicinity of Ski Butternut
This smoke-free bed & breakfast features coffee/tea in a common area, concierge services, and express check-in. Free WiFi in public areas and free self parking are also provided. Other amenities include express check-out.
The Barrington offers 7 accommodations with complimentary bottled water and coffee/tea makers. These individually decorated accommodations have separate sitting areas and include desks. Beds feature premium bedding. Flat-screen televisions come with premium cable channels.

Bathrooms include bathrobes, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and portable fans. Housekeeping is provided daily.

- "Great stay, the room was as advertised, delicious breakfast included and great location. Will stay again. " - "As always, our stay at The Barrington was wonderful. The rooms are large, lovely and the bed comfortable. The service is great and everyone is so friendly and accommodating! The breakfast is delicious. We truly enjoy our stay, every time!" - "We absolutely loved our stay at The Barrington. The staff is lovely. The room was huge, beautiful and quiet. The breakfast was incredible. We will definitely be back. "

Situated in Great Barrington in the Massachusetts region, Windflower Inn features accommodation with free WiFi and free private parking. The bed and breakfast offers a flat-screen TV and a private bathroom with a hairdryer, free toiletries and shower. Some units have a seating area and/or a terrace. Guests at Windflower Inn can enjoy hiking and skiing nearby, or make the most of the garden. Hudson is 33 km from the accommodation, while Saugerties is 46 km from the property. The nearest airport is Bradley International Airport, 85 km from Windflower Inn.

Air Conditioner • Internet • Parking

Relax in the Berkshires at this peaceful riverside retreat with a sauna. The guesthouse is an attached wing of a private residence with separate entrance and lots of privacy. With a beautiful 4 acre grounds next to the lush clean Green river for dipping, it is great for everyone! The land opens to an expansive bucolic view of the valley and mountains. 8 minutes to the town of Great Barrington, 10 min to Catamount Ski area, and under 20 min from many more southern Berkshire attractions.

Guest access
Welcome.
As you approach 65 Pumpkin Hollow Road, you will pass over a small bridge. The property is directly after the bridge on the right hand side, a white house with a U-shaped driveway. Take the second driveway entrance after the bridge (near a red three bay garage).

You can pull into the parking spot which is on the left side of the house when you are facing it.

Take the stone foot path around the left (North) side of the house and it will bring you ti the back side of the house where the entrance is.

Other things to note
The second bed is a fold out couch good for 1 smaller person.

Heating • Essentials • Refrigerator • Cooking basics • Hot water • Outdoor playground • Bathtub • Smoke alarm • Bed linens • Wifi

Welcome to your peaceful oasis in the Berkshires! The charming studio features an open layout with a plush bed, reading chair, and convenient workspace boasting high speed internet. Enjoy the refreshing in-ground pool and spacious patio, perfect for lounging under the sun. The full bathroom ensures all your needs are met, while a coffee bar adds a touch of luxury to your mornings. Complete with air conditioning, this idyllic retreat is the perfect getaway. Book your stay today!

The space
Escape to our peaceful studio nestled in the heart of the Berkshires, where the beauty of nature meets modern comfort! Located just a stone's throw from Long Pond, this private gem is perfect for anyone seeking a tranquil getaway surrounded by woods and wildlife.

*** Pool is open from Memorial Day to Labor Day.

Arrival & Outdoor Space
As you pull into the driveway, you’ll immediately sense the serene ambiance that makes this property truly special. The expansive front lawn leads to a large deck area, where you’ll be welcomed into your woodland escape. Be mindful of the pool! The outdoor space is designed for relaxation and enjoyment, featuring a sun-soaked patio with loungers for soaking up the sun, a grill area for delightful barbecues, and an outdoor fire pit for cozy evenings under the stars.

Studio Interior
Step inside the studio, where you’ll discover a beautifully decorated space that combines comfort and style. Snuggle into the plush queen bed, perfect for a restful night’s sleep after a day of adventure. A cozy reading nook invites you to unwind with a good book, while a small private workspace allows you to catch up on any tasks if needed. For your convenience, the studio is equipped with a mini fridge stocked with essentials and a coffee station ready for those early morning brews or leisurely afternoons.

Well-Appointed Bathroom
The studio features a thoughtfully designed bathroom stocked with all the essentials, ensuring you can freshen up before heading out for a night on the town. You’ll find everything you need, from fluffy towels to quality toiletries, making your stay both comfortable and convenient.

Endless Outdoor Activities
Located just minutes away from Long Pond, you’ll have ample opportunities for outdoor fun, including swimming in the pool, hiking, and exploring the breathtaking natural beauty the Berkshires have to offer. With charming local shops and delicious dining options in Great Barrington, you’ll find plenty to explore.

Experience Serenity
This woodland retreat promises a peaceful and rejuvenating atmosphere, perfect for couples, solo travelers, or anyone looking to recharge in a stunning natural setting. We invite you to unwind and enjoy the beauty of your surroundings, all while feeling right at home.

Book your stay today and get ready to create unforgettable memories in our slice of paradise in the Berkshires!

Guest access
Guests will have access to the yard, the patio area, the pool, and the fire pit. The main house will be empty but won't be available during the stay.

Bed linens • Pool view • Hot water • Conditioner • Ethernet connection • Air conditioning • Shampoo • Essentials • Ceiling fan • Body soap

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

The space
PLEASE READ
The guest house is in a small rural village with very little cell service in the area. SPIRAL STAIRCASE leads up to a LOFT style bedroom and bathroom.

Guest access
Entire guesthouse

Hangers • Hot water • Hair dryer • Bathtub • Shower gel • Cleaning products • Essentials • Shampoo • Conditioner • Body soap

Come enjoy the Berkshires in a newly renovated post and beam barn. Located walking distance to Egremont, and a short drive to the charming town of Great Barrington, where you will find many shops and restaurants.
In the mood for music? Take a short walk and you are at one of the best music venues in the Berkshires.
This space is all one level and has two separate bedrooms and a day bed/ trundle. The kitchen does not have an oven but you can use the induction cook top to whip up easy meals.

The space
Our lovely guest barn has everything you need for a great stay in the Berkshires. There are two bedrooms and a daybed/ trundle located in the living room.

Our kitchen has lovely French doors leading out to the back deck. You will find an induction cooktop as well as pots and pans that work with the induction cooktop. There is also a microwave and coffee maker that can be used with K cups or ground coffee. Please note there is no oven.

We are located 8 minutes from Catamount Mountain resort and 15 minutes from Ski Butternut. We are also a short 10 minute drive into downtown Great Barrington, as well as conveniently located in the quaint village of South Egremont where we have newly constructed sidewalks.

Guest access
You will have access to the entire downstairs of our guest barn. We do have one locked storage closet on the downstairs level. The upstairs is an office that we keep locked.

Enjoy our spacious backyard while staying within arms reach to all of the best amenities in the Berkshires, but feeling like you are away from it all.

Other things to note
Charcoal grill is located outside bring your own charcoal.

We do our best to keep the house extremely clean but we are in the country and occasionally you may see some bugs inside.

We drink the tap water!

Our hot water heater is environmentally friendly. Please do not run the water until you are ready for a shower.

Air conditioning • Crib - available upon request • Ping pong table • Babysitter recommendations • High chair - available upon request • Books and reading material • Hangers • Hot water • Bed linens • TV

Come enjoy our renovated Barn Guesthouse. Originally a part of the 250+ year old farm and property, the updated Barn offers sunset views of the surrounding meadows, a private bedroom, outdoor shower, and unheated saltwater pool in the summer months (Memorial Day weekend - Sept 15). A great place to come relax after a day adventuring around the Berkshires. Just 15 minutes to Great Barrington, 20 minutes to Stockbridge, you can enjoy the local scene as well as a quintessential country setting.

The space
Please note before you book, we do not allow outside guests on the property.
This unique Guesthouse maintains the original rustic barn-like feel with exposed beams, pine boards, and large open spaces. Sweeping pastoral views to the west provide the best sunsets in the Berkshires.
With a largely open floor plan, the main floor consists of the light-filled great room, bathroom, and the indoor and outdoor stall showers. No tub.
The spacious bedroom with east facing windows is located on the 2nd floor and includes two twin beds and one king size bed. There is no central AC, but there is a window AC unit in the bedroom and a ceiling fan in the main room.
While there is no kitchen, we do offer a small fridge/freezer, coffee maker, and electric hot water kettle. There are multiple wonderful local coffee and breakfast spots 5 minutes down the road. We do not allow guests to bring in cooking equipment such as hot plates, toaster ovens, grills, etc.
Enjoy a cocktail and the sunset from the Adirondack chairs outside or fall in the salt water pool for the afternoon. Please note that the pool is not heated and that pool access is ladder only (no stairs).
The property neighbors an active horse farm. Please expect roosters crowing, geese honking, and tractors driving. There are no pets allowed in the guesthouse, no exceptions.

Guest access
The guesthouse is private and the space is yours to use.

Other things to note
We have an Australian cattle dog, Sid, who may greet you if you cross paths in the driveway but we generally try to keep him in the house if you’re coming and going.
We also have a goose named Benjamin who is very vocal but friendly (really!), but the Guesthouse outdoor space and pool is fenced so she won't be in your space while you're here but again you may cross paths with her in the driveway.
Just to reiterate, there is no kitchen or grill. Just coffee maker and hot water heater.

Hot water • Carbon monoxide alarm • Bed linens • Outdoor shower • Smoke alarm • Air conditioning • Clothing storage: dresser • Hangers • Body soap • Hair dryer

Your perfect Berkshire getaway awaits in this 2 BR, 1.5 BA guest house on Long Pond Rd in Great Barrington. Hiking is just steps away with beautiful views of the mountains and Long Pond. An amazing location central to all the Berkshires has to offer! Vacation rental available for 1 month minimum, up to 6 months. See notes section.

-7 minutes to restaurants + shopping in downtown GB
-19 min Catamount Ski Mountain
-20 minutes to Tanglewood + downtown Lenox

The space
This home is a guest house which is part of a large property, but is completely private and almost a football field away from the main house. This is not a shared place.

The guest cottage has been recently updated with new furniture, decor and upgrades!

Both bedrooms are located on the ground level. The first featuring a king bed and desk for those who need to work from home. The second bedroom; has a twin daybed. This bedroom has access to the half bath and the exterior door to the back yard. There is a garage bay with plenty of room for storing skis and gear.

On the second floor you will find a large sectional which pulls out to a queen bed. The living room features a Smart TV and spacious window seat. The dining area seats four guests and can also double as an additional work space. The full kitchen contains Microwave, toaster, coffee maker, small fridge, oven and cook top. A portable dishwasher is available and a full sized fridge is located in the garage.

The full bathroom/laundry room is also on the second level and features a walk in shower.

All the rooms have air conditioning and heat.

The fully fenced in backyard provides plenty of privacy to relax in the hammock or around the fire pit. Enjoy a meal outside with the outdoor dining area and gas grill.

Long Pond is a reservoir in Great Barrington. It is a beautiful serene spot surrounded by nature. This is not a swimming/boating pond, but there is plenty of hiking all around the area. Pfeiffer Arboretum is just down the road which is a Land Conservancy on Long Pond featuring a " .7 mile walking loop through diverse forest and wetland ecosystems".

Although you will feel far from it all, downtown Great Barrington is just a quick 7 minute drive for shopping and restaurants! Butternut Ski Area is located only 14 minutes away and Catamount Ski Mountain is 19 minutes from the property. Both Tanglewood and downtown Lenox are only a 20 minute drive.

Guest access
Guests have access to all spaces within this home including one garage stall for ski storage.

Other things to note
LOCATION: This private guest house is surrounded by hiking trails and central to plenty of Berkshires activities.
PETS: Small dogs may be allowed with owner approval. Reach out with info about your pet prior to booking. A $100 pet fee will be incurred upon pet approval and booking. No multiples.
PARKING: This long driveway is shared by 1 additional home. There is plenty of room for off street parking up to 4 cars.
*There is a 31 night minimum requirement, however occupancy tax is automatically removed if booked 32 nights or more.
*This property can accommodate 5 guests total. The living room sofa also pulls out to a sofa bed.
*Town of Great Barrington Registration No: 003792

**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

Public Goods body soap • Essentials • Cleaning products • Hair dryer • Public goods shampoo • Public Goods conditioner • Hot water • Washer • Shower gel • Free dryer – In unit

Bikers, walkers, nature-lovers: this charming cottage offers spectacular views of rolling hills and verdant meadows, delightful pool, outdoor excursions and culture galore. It's only minutes from Great Barrington with restaurants, music, theater.
The Berkshires in spring, summer and fall are alive with beauty, ideal for your restoring getaway.
Dogs $25 extra/night, less per wk.
PLEASE answer our Covid questions, sent to you pre-booking!!

The space
Perfect for any couple needing an extended break from city life, this gem of a studio cottage offers lengthy stays that will appeal whether you are an active hiker or biker, or just want to sit under the trees or by the pool with a good book (or your Kindle or iPad) and savor the unsurpassed scenery. You'll be on a secluded country lane but only 7 minutes from Great Barrington. It's an easy drive to all area attractions, music, theater, and close to great Appalachian Trail hikes. The nearby roads are also ideal for biking and walking It's the sole cottage on the property, 50' from the main house but with its own entrance. And there's plenty or private time for guests at the sparkling pool. Complimentary bottle of wine and chocolate.

Spring and summer stays of a month or more are available.

(Note: as of 7/1/19, the state is requiring 11.7% in state and local tax Certif # C0086021130. Any taxes not charged by airbnb will be included in special pricing sent to guest.)

Guest access
Outdoors: Quiet grounds, classic wooden bench with side table, sparkling in-ground pool, outdoor lounge chairs. Kayaks, lawn chairs available for excursions.

Weber charcoal barbecue available for dedicated guest use.

Indoors: bedroom/sitting room,kitchenette (sink and dishes, microwave, toaster,coffeemaker, full fridge), full bath with tub and shower. Windows on 3 sides, ceiling fan, closet space, extra blankets for cool nights.

The area: it's an easy drive to music and dance, theater, museums, restaurants, scenic views and hiking trails

Other things to note
PETS: Dogs welcome if well-behaved. Maximum of two dogs. Dogs must be leashed on the property and cannot go into the pool. Inquire before booking

Bed linens • Extra pillows and blankets • Hangers • Shampoo • Essentials • Bathtub • Body soap • Mountain view • Hair dryer • Hot water

Our historic home was built in 1797 and has welcomed guests and family for over 200 years. Every room speaks to the history of New England and the town of Mill River.
Included nearby are iconic venues of the Berkshires which include Gedney Farm, Butternut Ski Resort, the Appalachian Trail, Monument Mountain, Tanglewood, Jacob's Pillow, Barrington Stage Company, and Shakespeare and Company as well as little known, more local places such as Umpachene Falls and the Mill River Store.

Other things to note
"Covid-19 Update: Due to the Covid-19 pandemic, our bed and breakfast will be taking guests Friday through Sunday, only.  To ensure proper social distancing, we will be accommodating guests at half capacity and following all state guidelines."

Heating • Air conditioning • Hot water • Hair dryer • Lock on bedroom door • Essentials • Hangers • TV • Iron • Smoke alarm

One of the largest rooms in a 5 guestroom Bed & Breakfast, features a king sized bed as well as a twin sized day bed.

The space
A king suite within a luxury 5 guestroom Bed & Breakfast in Great Barrington Massachusetts.

Guest access
There are multiple common spaces within the house for guests to enjoy. A hot breakfast is included with each night's stay.

During your stay
As owners of the B&B, hosts are onsite throughout your stay and happy to provide for your needs.

Other things to note
Each of our eclectically well-appointed rooms include Brooklinen luxury bedding for maximum sleep comfort and MALIN+GOETZ bath products for indulgent pampering. Additionally, each room comes equipped with a small refrigerator, a Keurig coffee maker and a Crosley record player, inviting you to enjoy our expansive vinyl collection.

Hot water • Shampoo • Heating • Hangers • Hair dryer • Lock on bedroom door • Bed linens • Iron • Air conditioning • Extra pillows and blankets