Bed and breakfast holiday rentals in The Berkshires

Find and book unique bed & breakfast rentals on Airbnb

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Popular amenities for bed & breakfast rentals in The Berkshires

Family-friendly bed & breakfast rentals

Superhost
Cabin in Smallwood
4.86 out of 5 average rating, 189 reviews

Lake Front Catskills Lodge

YusufRating, 5 stars1 week ago
Absolutely gorgeous place. Was so peaceful and nice. Meghan was friendly and responded very fast when we needed something. Would love to come back and enjoying the kayaks on the beautiful lake again!
Superhost
Private room in Bovina Center
4.91 out of 5 average rating, 284 reviews

Highlanders View - The Suite, Hot Breakfast incl.

NikolajRating, 5 stars2 weeks ago
This was our second stay at Patty and Liam’s place, and we loved it just as much! Cozy space, gorgeous view, and close to both trails and towns. The included breakfast was a treat, especially the homemade maple syrup. Liam was super welcoming and shared great local tips. Don’t miss the unit with the hot tub—it was a real treat after days filled with hiking. Highly recommend it!
Guest favourite
Home in Manchester
4.97 out of 5 average rating, 58 reviews

BREAKTIME

SatoruRating, 5 stars5 months ago
5 of us stayed at David's place for our family ski vacation and all of us loved the location and the house. the house was as described and has so many linens and amenities. it's 30 minutes to Stratton Ski Report and 5 minutes to downtown Manchester where you can find anything, including Shaws supermarket. It's a great location and house and we are looking forward to come back to this place next year for our family vacation. Thanks
Superhost
Home in Rhinebeck
5 out of 5 average rating, 4 reviews

Unique Converted Carriage House and Barn Compound

JoanRating, 5 stars45 months ago
This house was the perfect place for our family get together. We were able to use both dwelling and socially isolate while indoors. The grounds are extensive and nicely cared for. There were plenty of gathering spots outdoors where family could gather comfortably while maintaining distance. These are cray times, but this property was well suited for our family needs. The garden is gorgeous and there was plenty of room to spread out for a softball game or badminton, but intimate enough to find a nice corner to read or just relax. The location was very good as well. It was a short distance to the walkway over the Hudson (30 min) and to Lake Minnewaska State Park (40 min). This was our first trip to Hudson Valley but will not be our last.
Top guest favourite
Private room in Amherst
4.91 out of 5 average rating, 212 reviews

OrchardSlope

StephenRating, 5 stars1 week ago
We had a lovely and very comfortable stay at Michele’s place. They made the trip a wonderful and memorable weekend.
Top guest favourite
Private room in Gilsum
4.96 out of 5 average rating, 369 reviews

Solar Living Emerson Brook Forest 1

LauraRating, 5 stars3 weeks ago
Staying with Valerie at her home was the perfect end to an already magical weekend at Bethel Farms where I participated in a spiritual retreat, which was very rejuvenating but also a lot of energy work. Staying at Valerie's was the perfect spot to recoup for a day before heading back to Philadelphia!
Guest favourite
Home in Beacon
4.89 out of 5 average rating, 166 reviews

Hiking Hideaway on the Ridge

ZohraRating, 5 stars6 days ago
Rosemary and Ed were warm hosts. They had great advice on where to join hiking trails surrounding their property. The space is welcoming, clean and as described. Rosemary kindly offered us some fresh veg from their garden! Would 100% recommend.
Top guest favourite
Private room in Wells
4.96 out of 5 average rating, 414 reviews

Endless Brook Farm B&B w Sauna, Hot Tub, Breakfast

MaryRating, 5 stars2 weeks ago
Catherine's home was just right for us, private setting in the country, a suite all to ourselves, use of the kitchen and beautiful garden and area to walk in. We could hear the peepers by the near-by pond once it got dark. Catherine and Todd were wonderful hosts and we enjoyed our conversations together. We learned about a park just down the road with a trail to the top of a small mountain that overlooks the near-by lake. We would love to stay again in the future.

Bed and breakfast rentals with breakfast

Top guest favourite
Private room in Deerfield
4.99 out of 5 average rating, 184 reviews

Queen bed suite, full breakfast, five stars

Cristiany and ToddRating, 5 stars2 weeks ago
Yet another wonderful 5-star stay at Jane & Karl's lovely home in Deerfield. Delicious homemade breakfasts, spacious and clean rooms, and always a warm welcome from Jane & Karl. Have stayed over 10 times across 3 years, and every time has been great - and there's always an improvement each time!
Top guest favourite
Private room in Belchertown
4.95 out of 5 average rating, 474 reviews

Laid Back Victorian, private BR, LR and bath

MarisaRating, 5 stars4 days ago
I am so honored to have been one of the last guests who had the privilege of staying in this beautiful home. Thank you, Chris and Fran, for the wonderful conversation, the magic tricks, delicious local breakfasts, recommendations, and opening your charming historic home to our travels!
Top guest favourite
Private room in Bennington
5 out of 5 average rating, 121 reviews

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

MontseRating, 5 stars2 weeks ago
As usual, everything perfect at Ernie's. It's a great place to be.
Guest favourite
Cottage in Lyme
5 out of 5 average rating, 18 reviews

Bucolic Farm On A Country Road

K.K.Rating, 5 stars1 week ago
We could not have asked for a nicer place to stay~~~~clean, comfortable, woke up every morning hearing the bird’s singing. Felt like home. And Lori was a wonderful host! Thank you!
Guest favourite
Private room in Sunderland
4.94 out of 5 average rating, 198 reviews

Private 2nd Floor Studio Apartment With a View!

GayleRating, 5 stars4 weeks ago
Felt like we were nestled in the range of Mount Toby. The property and studio were super quiet, super non scented and clean with plentiful views to awe at. We needed ths peaceful trip while watching our son graduate. We are huge fans of Pioneer Valley. We know this area well so we took advantage of all great foodie places and all nature locations we could pack in. We would love to visit your place again! A slice of heaven for us
Guest favourite
Private room in Troy
4.97 out of 5 average rating, 357 reviews

The Sara Tracy House, Eliot Room

MicheleRating, 5 stars1 week ago
The inn was beautiful inside, the door to enter is down a little brick paved alley so it is set back from the street, which is very nice. The street itself is still a work in progress. There is still a lot of fixing up going on so it may seem a bit disconcerting, but step inside the inn and all your worries will melt away. It was quiet (because it is set back from the street) and very clean, beautiful and comfortable. We had a great night's sleep and a lovely breakfast the next morning: nice yogurts, fresh fruit and granola, juice and tea and coffee and muffins, fresh from a bakery that morning! We will certainly stay there again when we visit our son at RPI!
Superhost
Private room in New Haven
4.79 out of 5 average rating, 280 reviews

Carriage House "Rembrandt"

康弘Rating, 5 stars2 months ago
Remy was always responsive to our questions and requests, and regularly checked in to see how we were doing. The location is excellent and very safe. It’s especially convenient for anyone visiting Yale, as you can easily reach any of the campuses from the nearby bus stop. I would love to stay here again if I have the chance.😊
Top guest favourite
Private room in Brimfield
4.95 out of 5 average rating, 412 reviews

New England Escape

EmilyRating, 5 stars2 weeks ago
I was thrilled with my stay at this beautiful Airbnb, it met and exceeded all my expectations. The place was clean, quiet, private, and equipped with everything I needed to be perfectly comfortable. I would definitely stay again, and highly recommend to anyone who needs a place to stay!

Bed and breakfast rentals with a patio

Top guest favourite
Private room in Stillwater
5 out of 5 average rating, 18 reviews

Storybook Cottage - Bird House Room

ZacharyRating, 5 stars3 weeks ago
Kathleen was very kind and informative when we checked in. She has a wonderful bed and breakfast and the food she prepared is phenomenal. She made us feel very welcome. Would definitely recommend to anyone staying in Stillwater or surrounding areas
Top guest favourite
Private room in Amsterdam
5 out of 5 average rating, 33 reviews

One Half Historic Farmhouse

TravisRating, 5 stars2 weeks ago
What an awesome place, and an awesome host! I had an eight-hour drive to make when I left. Priscilla volunteered to serve breakfast at 5:45 AM. Great breakfast. Great host. I even got to relax reading a book in front of the fireplace. It wasn't lit, but still so cool. She offered to make a fire and I declined. Thank you so much for your hospitality! Travis Lee
Guest favourite
Private room in Litchfield County
4.92 out of 5 average rating, 12 reviews

Private en-suite Bedroom in Historic Inn

KarleneRating, 5 stars9 months ago
We totally loved our stay! The town of Norfolk is so quaint. But Airbnb bed-and-breakfast, we felt right at home really loved the breakfast in the morning when we all sat around the table and had conversations with all the guests that were staying. I would definitely stay there if we return to the area.
Guest favourite
Shared room in Poughkeepsie
5 out of 5 average rating, 28 reviews

Tiny space double bed corner with privacy screen

JackRating, 5 stars6 months ago
The bed was nice and comfy! Appreciate the stay!
Top guest favourite
Private room in Rensselaerville
5 out of 5 average rating, 39 reviews

Cozy Queen room in Historic Bed and Breakfast

JessicaRating, 5 stars3 weeks ago
The Catalpa House was the sweetest bed & breakfast you could find in the area. Ellen was so kind, cooked us up an immaculate breakfast and gave wonderful recommendations for the short amount of time we had in the area. The room was super comfortable and she was extremely accommodating to anything we need throughout our stay. The town is a very sleepy town with not much to do, but beautiful surroundings. There were trails and a waterfall hike just up the road that kept us occupied and that we enjoyed the morning after our stay. Would definitely stay again if ever in the area.
Top guest favourite
Private room in Belchertown
4.98 out of 5 average rating, 106 reviews

The Lacey Rose - The Golden Room

KeithRating, 5 stars4 weeks ago
The Lacey Rose is an absolutely stunning Victorian home built in the early 1800’s. Every single detail of the home from the paintings and artwork on the stained glass windows, to the ornate ceilings and walls, to the beautifully curated outside space complete with a pool and several relaxing areas with chairs and tables to lounge. Denise was friendly and helpful, and made our breakfast experience absolutely flawless!!! I can’t recommend this place enough, please if you are in the are you must check it out! This is the epitome of what one expects when booking a B&B at such a fabulous location. Thank you again Denise, I’m sure I’ll be back!!
Guest favourite
Hotel room in Warwick
4.88 out of 5 average rating, 144 reviews

The Warwick Inn Boutique Little York Loft.

MelvinRating, 5 stars2 weeks ago
Such an awesome place! Very cozy, clean and great experience. I recommend this for a night or two away.
Top guest favourite
Private room in Poughkeepsie
4.96 out of 5 average rating, 110 reviews

Hudson Pond · Hideaway King Suite

MariaRating, 5 stars6 days ago
Our stay at Nicole’s place was lovely. We had a nice walk around the pound. It was very peaceful

Destinations to explore