Bed and breakfast vacation rentals in The Berkshires

Find and book unique bed and breakfast rentals on Airbnb

Top-rated bed and breakfast rentals in The Berkshires

Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

Private room in Sandisfield

4.92 out of 5 average rating, 137 reviews

Hospitality in the Berkshire Woods

Enjoy a rustic wooded retreat up in the cool Berkshire hills, surrounded by nature and wildlife, in a quiet, secluded, safe and peaceful setting, yet very close to top-notch cultural and recreational attractions. Nearby trails, pristine lakes and woods offer hiking, swimming and cycling. Experience the absence of mechanical sounds and the centering presence of rustling leaves, birdsong, and owls hooting at night. Behold a star-studded black night sky without artificial light. Breakfast included!

Guest favorite

Guest suite in South Hadley

4.83 out of 5 average rating, 84 reviews

River front guest suite

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 8 1 bathroom Covered parking Dock available Kayaking Boat rental available Paddle bikes and boards Views Fire pit Tour boat next door at Brunelle’s Marina. Patio Ice machine Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails

Top guest favorite

Private room in Amherst

4.93 out of 5 average rating, 207 reviews

BigSkyHilltop: Queen & single bed, full breakfast

BigSkyHilltop is located in a picturesque area 10 minutes from Amherst Center and close to 5 colleges; views for 50 miles; There are lots of hiking and cross country trails close by. If you'd prefer a little more privacy and a private bathroom, check our other Airbnb listing titled 'Private Suite and bathroom/full breakfast.' Joan and Josette have been fully vaccinated against Covid 19 to protect our guests -- we require that our guests have also been fully vaccinated before their arrival.

Top guest favorite

Private room in Bennington

5 out of 5 average rating, 119 reviews

E and E’s B and B Queen Bed Rm+ Pool & Hot Tub

We are located on 16 East Street in Bennington VT minutes from rt 7 and route 9 Main Street. Summer is more like a mini resort with a beautiful in-ground pool and Hot Tub. We also feature plenty of in-room USB phone plug-ins and extensions, in room TVs.. Perfect for couples or bring a child. (Extra Fees for children over 2 years. Sunning Deck or shaded patio dining or just relaxing with a good book poolside or the indoor lounge with a drink. We’ve got you covered. Many unexpected amenities.

Guest favorite

Cottage in Lyme

5 out of 5 average rating, 15 reviews

Bucolic Farm On A Country Road

Lovely private 1 bedroom apartment with shared entry. Located in bucolic Lyme Ct. which has nearby beaches, tourist attractions, nature parks, small town living, hiking etc. Sparkling clean! Fully equipped kitchen, dining and living spaces incl laundry. Enjoy the outdoor sitting area with sounds of nature and wildlife. Comfortable furnishings, include a sleeper sofa for an extra guest or 2! Private and peaceful yet close to shopping, dining, area attractions and nature pursuits.

Top guest favorite

Private room in Warwick

4.98 out of 5 average rating, 102 reviews

Glenwood Farmhouse Bed & Breakfast - Second Suite

Victorian farmhouse (c. 1855) minutes from the Village of Warwick, Mountain Creek Ski Resort, local orchards, wineries, and Appalachian Trail. This master room has a king-sized bed and en suite bathroom with soaking tub and separate shower stall. Your stay includes a country farm breakfast with eggs from our chickens, produce from our garden (in season) and other local ingredients. Swimming pool and lounge for guests. ATTENTION: THERE ARE TWO CATS ON THE PREMISES.Check in 2:00 pm.

Top guest favorite

Private room in Hyde Park

4.98 out of 5 average rating, 219 reviews

Hidden Gem with Pool~ The Harvest Guest House

Relax and unwind in a charming Georgian home, nestled on 6 acres of serene wooded acreage with a beautiful pool, patio, gazebo, and firepit. With your own entrance and 2 private bedrooms, you will enjoy a peaceful retreat. The home is conveniently located near the Roosevelt and Vanderbilt Estates, Walkway Over the Hudson, Culinary Institute, and Marist College. Whether you're looking to relax or explore the stunning Hudson Valley and historic estates, this property is an ideal escape.

Superhost

Private room in New Haven

4.79 out of 5 average rating, 280 reviews

Carriage House "Rembrandt"

This is a locked bedroom inside our Carriage house Kitchen and bathroom, living and dinning are cleaned daily All shared by 2 other single rooms central heat & air conditioning The Rembrandt room has hardwood floors ,a full size bed, lg. Desk, Dresser and closet, skylights add charm to the beamed ceiling. Free Breakfast foods and snacks in our stocked self serve kitchen Key less entry and free laundry room in the man house We provide linen services towels and sheets.

Superhost

Private room in Bovina Center

4.91 out of 5 average rating, 162 reviews

Highlanders View-Cottage room, Hot breakfast incl.

This is 1 of 4 rooms we offer (If this room is full, check the URLs below of the other rooms we offer). As with our rooms, we offer the most spectacular view of the Catskills. This, coupled with our famous hot farm-fresh breakfast and modern amenities provides our guests with an extraordinary stay that the best memories are made of. We border on the Plattekill State Forest, so enjoy hiking, biking, skiing, or hunting right off the property. & unwind in the hot tub

Top guest favorite

Private room in Coventry

4.99 out of 5 average rating, 196 reviews

Jan's Phoenix Nest Lakefront B&B

15 minutes from the University of Connecticut on pristine Coventry Lake. Our B&B has all modern amenities. We offer a second floor bedroom and a private bath in our recently built home. Also a private sitting room and balcony overlooking the lake. Come and enjoy beautiful Coventry Lake and delicious breakfasts each morning. Food allergies? No worries, we are happy to provide wonderful gluten, egg, and/or dairy-free breakfasts. Hosted by Jan & Tom.

Top guest favorite

Private room in Belchertown

4.98 out of 5 average rating, 193 reviews

Eclectic Victorian Charm

Comfort, character and charm on our second floor. Save your dates now for special occasions and the Brimfield Antique shows. Queen bed, small table, shared full bath with clawfoot tub and shower surround. Spacious room with Firestick TV, microwave, refrigerator, coffee maker. Light complimentary, self serve breakfast in main kitchen to eat in dining room or your private space. We encourage you to read our full description.

Superhost

Private room in East Chatham

5 out of 5 average rating, 3 reviews

The Inn at Silver Maple Farm - Upper Lodge

The Upper Lodge is a rustic and private hideaway with an Adirondack feel to it. It features a king-sized bed. This slightly smaller room is located on the second floor; part of the room has a slanted ceiling along the roof line. Enjoy your private little library, smart TV with cable, and wi-fi. You’ll love the stylish décor of this charming place to stay.

0 of 0 items showing

What guests are saying

Romantic Room near Hunter Mountain

5 out of 5 average rating, 70 reviews1 month ago

We booked a last minute getaway and this was IDEAL. Sean and Kelly’s beautifully restored home is cozy and so immaculately beautiful. The downstairs common areas are perfect for curling up by the fire with a book and a cup of tea/glass of wine. The bedroom was spotless, super comfortable bed, sparkling clean bathroom and awesome jacuzzi style bathtub. The hosts are extremely friendly and amazing people. They made us feel right at home and welcome, we thoroughly enjoyed chatting with them about local history, wildlife, and their story. Can’t wait to come back here again!

Private room in Haines Falls

What guests are saying

Northville Room at Maguire’s Great Sacandaga B&B

5 out of 5 average rating, 12 reviews33 months ago

Patricia is a warm, accomodating host and keeps up a beautiful, historic property right on the lakefront of Sacandaga. This B&B is well furnished, comfortable beds/linens, and includes any amenity you'd need for a relaxing summer retreat (in ground pool, fire pit on the water, kayaks, etc.). Not to mention, Patricia also makes a delicious breakfast every morning. Looking forward to our third stay next July!

Private room in Mayfield

What guests are saying

Room 3 Cold Spring Hotel (Main St.)

4.83 out of 5 average rating, 83 reviews4 days ago

Just got back from a wonderful one night stay with Jimmy. We were greeted warmly, with humor and great local recommendations. The hotel is a convenient 10-15 minute walk from the Cold Spring Metro North stop. The room was exactly as pictured: quaint, clean, and cozy. We were offered discounts on breakfast and additional nights stays, which was a great touch. Jimmy was kind enough to hold our luggage and let us use his cafe's restroom after we checked out and explored Cold Spring for the day. If I come back to explore the multitude of hiking trails in the area, I wouldn't hesitate to stay with Jimmy again. I'm also recommending his hotel to any friends/family planning a trip to Cold Spring. Thanks for the great stay! - Taylor and Chris

Hotel room in Cold Spring

What guests are saying

Fenn Farmstead - w/farm-to-table breakfast 1 BR

4.98 out of 5 average rating, 62 reviews1 month ago

I had a wonderful stay with Jim and Monique! They have a beautiful and comfortable house in a gorgeous setting and are the perfect hosts. My room was spacious and well appointed; loved the barrel ceiling. The bed and linens were very comfortable and I had two great nights of sleep. Monique's breakfasts are truly outstanding and a great start to my day. Most of all, Jim and Monique are lovely people and I enjoyed getting to know them. I will definitely look to stay with them again next time I'm in the area.

Private room in Mount Holly

What guests are saying

Arts Inn - The Matisse Room

4.97 out of 5 average rating, 29 reviews1 month ago

Heidi goes above and beyond for her guests. Her home is warm and welcoming making you feel right at home. The complimentary breakfast is a nice touch. we had the pleasure of meeting Heidi and it was such a pleasure getting to know her. She also gives great recommendations on where to go around town. We will definitely be coming back for another stay. Thank you Heidi, Randy, and of course their pup Satchmo for a wonderful stay. We are grateful you open your home to us all.

Private room in Fleischmanns

What guests are saying

The Town View

5 out of 5 average rating, 3 reviews48 months ago

What a treat! I grew up in Madison and didn’t realize this amazing bed and breakfast was right under my nose! Michael was incredibly friendly and helpful and the space was fantastic. I will absolutely be coming back and highly recommend it to anyone looking for a beautiful space, central location and delicious breakfast!

Hotel room in Madison

What guests are saying

Sheffield Lodge - Ramblewood Master

4.98 out of 5 average rating, 45 reviews9 months ago

Susan's place is charming. Our room was lovely, and you couldn't ask for more peaceful and beautiful wooded suroundings. Guests are treated to a tasty and very satisfying homemade breakfast. You choose the time to be served. Susan and our fellow guests were interesting to talk to, which was the frosting on the cake. And one more thing: I mistakenly left a piece of luggage there. Susan was very responsive to my call for help and is sending it back to me today. Susan, we'll be sure to see you again.!Thanks for a great stay!

Private room in Sheffield

What guests are saying

Large Bedroom With Private Bath in Beekman Mansion

5 out of 5 average rating, 56 reviews1 week ago

The house was lovely and John was very responsive to my texts. When we arrived, the caretaker, Raphael, was absolutely amazing. He was super friendly and extremely helpful. Breakfast was wonderful, and he was kind enough to bring us water and coffee while we sat in the parlor. The tub in the grey room was amazing an the walk around the property was nice also. 10/10 will recommend!

Private room in Middleburgh

What guests are saying

Empire Room, Rose Cottage B&B

4.94 out of 5 average rating, 32 reviews1 week ago

Hosted by an actual earth angel, Rose Marie’s property is a haven in this sleepy little hill town. Every room is well appointed & the suites are comfortable and beautiful! Rose has ‘the eye’ and everything from the linens to the fully furnished kitchen are thoughtfully designed. My husband is obsessed with this place & we are planning summer trips now that this is “our” place! We cannot wait to explore outside where she has extended the inspired & peaceful vibe of the interior well into the conservatory behind the house and the yards. You won’t regret staying here at all!

Private room in Orange

1 of 12 pages