Bed and breakfast holiday rentals in Lenox

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Popular amenities for bed & breakfast rentals in Lenox

Family-friendly bed & breakfast rentals

Superhost
Private room in Tivoli
4.89 out of 5 average rating, 124 reviews

Suminski Innski- Room 7- 2 flights up/shared bath

ChiaraRating, 5 stars10 months ago
Staying at Tim's was a fantastic experience for our family. We felt at home, part of a community made up of kind and welcoming people. Tim is much more than a host: he is a friend who makes his best to make his guests feel at ease and he is one of the most generous people I have ever met. The house is lovely and is in a pleasant place. We would like to return in the future.
Guest favourite
Private room in North Chatham
4.93 out of 5 average rating, 339 reviews

Arnold Farmhouse (Italianate - private bath)

KimberlyRating, 5 stars1 week ago
This is my 2nd stay at Vicki’s. I love the Victorian home she grew up in. It like stepping back in time and the surround area, farmlands, and towns are lovely to explore. Easy access from major road yet feels off the beaten path. I highly recommend staying here. I will be back.
Top guest favourite
Private room in North Chatham
4.96 out of 5 average rating, 536 reviews

Charming Eyebrow Colonial North Chatham, NY

PétronilleRating, 5 stars2 days ago
Very beautiful and quiet house in the nature. The room is large and the bed very comfortable. Thank you Susan for the warm welcome, great breakfast and nice conversation! Recommendation for diner for future guests : Bimi’s canteen and bar in Chatham !
Private room in Troy
5 out of 5 average rating, 17 reviews

Gardner Farm Inn - Oscar Wilde suite

AveryRating, 5 stars34 months ago
As the other reviews have mentioned, John is a beyond excellent host!!! And very responsive! He is also very knowledgeable and helpful regarding shops and restaurants in Troy. Nigel and Margaret (John’s greyhounds) are also very good companions at this Inn! The decor in the rooms and in the shared rooms and hallways is just beautiful and very interesting! And he serves delicious homemade breakfast! With alfresco dining as an option in the warmer weather.
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 Williamstown
4.96 out of 5 average rating, 120 reviews

Cozy 3 bedroom cape at end of road in Williamstown

JenelleRating, 5 stars3 months ago
Super charming home and guest space upstairs. We were looking for a comfy place to spend a few winter days with our Williams student and this fit the bill perfectly. Super close to campus, but the view out of the northwest window made it feel like we were in a wood cabin in the middle of the woods somewhere. Great communication with owner.
Superhost
Private room in Northampton
4.91 out of 5 average rating, 35 reviews

Large room on private floor

NancyRating, 5 stars9 months ago
I loved my stay. Yulia was very responsive to my messages as I arrived later than expected. The space is very private with a lovely garden outside the window. The bed was super-comfy with plenty of storage space in the room. And the shower water pressure was a dream! Both hosts were very friendly and made me feel welcome right away. I would definitely stay here again. Thank you both! Nancy
Private room in Hudson
4.84 out of 5 average rating, 775 reviews

Hudson, NY, 1br - 2 queen - June sale

MicheleRating, 5 stars1 month ago
We always love to stay with Ilja in his beautiful home. Ilja goes above and beyond to make you feel as comfortable as if you are home and this is appreciated. There was even a welcome note for us. Everything you need is available and there is a well stocked coffee and tea area

Bed and breakfast rentals with breakfast

Private room in Great Barrington
5 out of 5 average rating, 29 reviews

Granville House - Queen traditional

DanielleRating, 5 stars24 months ago
It was an absolute delight staying at The Granville House. The hosts were friendly and responsive, the space was beautifully curated and well appointed, and the location could not have been better. The breakfast provided was super tasty (muffin masters!), and the dining room vibes were excellent — music, decor, & the overall aesthetics of this place blew my mind. You can tell Terry and Terri have worked in hospitality for a long time and put a great deal of care into making the guest experience superb. I booked our long weekend on a whim and am so lucky there was availability; I have already recommended The Granville House to several of my friends.
Superhost
Private room in Hurley
4.75 out of 5 average rating, 4 reviews

Historic Creekside Bed & Breakfast with Hot Tub

JillRating, 5 stars7 months ago
Incredible place to stay! Had enormous cozy living room, bedroom, and bathroom to ourselves that was perfectly furnished with interesting farmhouse style decor. Bedroom and bathroom were clean, coffee and tea in the living room and games/books, and the best part was the outdoor space - lovely big backyard with lots of outdoor seating, cedar hottub (shared with other guests but no problem there!) and swimmable creek (enjoyed cold plunge -> hot tub in late Oct). Leaves were beautiful this time of year, easy 5-min bike ride to the O&W rail trail, and 10 min drive to Kingston and close to Woodstock too - Sarah gave great food recs. Can't wait to come back.
Top guest favourite
Private room in Enfield
5 out of 5 average rating, 83 reviews

Antique1242, Queen Elizabeth II suite. British

DaveRating, 5 stars1 day ago
Helen’s Bed & Breakfast is exactly that and one needs look no further to be able to experience that in a quaint Connecticut town just 10 minutes drive from downtown Springfield and, I think, about 10 miles from Bradley International airport. We came to watch our son participate in an Ironman competition there, so we took both of their rentable bedrooms and had the place to ourselves. Helen was very accommodating of our need to get him out the door at 5AM and then return around Mid-day so he could grab a shower afterwards….for us it sure beat having to worry with a usual hotel/motel stay. A nice Italian restaurant in town (Sofia’s) and a country diner nearby that was open for our early morning needs…. Rooms were decorated elegantly and a common living area downstairs was full of interesting British decorations to look at!
Top guest favourite
Private room in Norfolk
4.98 out of 5 average rating, 41 reviews

Maple House, Birch Room

StaceyRating, 5 stars6 months ago
Gorgeous home with an artist’s touch. Bill and Pamela are kind and thoughtful. Very much enjoyed my stay with them.
Top guest favourite
Private room in Sheffield
4.97 out of 5 average rating, 33 reviews

Beautiful Room in Hartfield House - The Berkshires

PeterRating, 5 stars7 months ago
We had such a wonderful stay! The house is historic, beautiful, and impeccably clean. Breakfast was delicious, with French press coffee and steeped tea that we loved. Missy the dog is a joy to be around and kept our dog entertained in the massive outdoor space. We truly felt at home, and the place felt very private. There’s so much to do in the area—great hikes, antique stores, and plenty of restaurants to explore. All in all, it was a very relaxing weekend getaway from the hustle and bustle of the city. We’d love to come back!
Superhost
Private room in Norfolk

C1 Carriage House at Blackberry River Inn

LindsayRating, 5 stars9 months ago
Oh....it was a great place to stay. I had my pup with me, and it worked out so well. Attended a concert down the street, and it was great to be back at the inn at a few minute's after the concert ended. Breakfast was wonderful, and the staff were so personable and accommodating . Look forward to my next visit!!
Top guest favourite
Private room in Northampton
4.94 out of 5 average rating, 208 reviews

Enjoy the River & Downtown Noho!

TracyRating, 5 stars2 weeks ago
Nancy was incredibly welcoming and made us feel right at home. She reached out in advance to ask for our estimated arrival time so she could greet us personally, and she also inquired about any dietary restrictions or special needs — such a thoughtful touch. The space was spotless, beautifully decorated, had everything we needed and we had our own private bathroom. Breakfast was absolutely amazing — thank you, Nancy, for the pie and parfait! My parents especially loved them. I’m sorry I didn’t respond to your message right away; I was caught up with graduation events. And we loved your cat!!!!! I would absolutely love to stay again!
Private room in Barkhamsted
4.55 out of 5 average rating, 20 reviews

Legends BNB Lodge RM 1 $79

IanRating, 5 stars72 months ago
What a great spot. We weren’t there for the fishing, everyone else was, but we still loved the place and enjoyed the company of the other guests.

Bed and breakfast rentals with a patio

Superhost
Private room in Red Hook
5 out of 5 average rating, 9 reviews

Mountain View Queen Suite w pool and patio

HollyRating, 5 stars22 months ago
Beautiful, relaxing getaway with friendly and helpful host. We truly enjoyed every moment in Diane's lovely home. The suite was spacious, comfortable, and full of amenities. We especially made time to enjoy the covered deck and pool, which were as wonderful as we hoped. The continental breakfast was incredibly helpful for getting our days started. Close to many restaurants, hikes, and lovely Hudson Valley towns. We would return in a heartbeat.
Top guest favourite
Private room in Stillwater
5 out of 5 average rating, 18 reviews

Storybook Cottage - Bird House Room

ZacharyRating, 5 stars2 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
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
Private room in Brattleboro
5 out of 5 average rating, 9 reviews

Purple Chef's cozy lair

JackieRating, 5 stars4 months ago
What a lovely and beautiful location amongst the woods... perfect living space, a wonderful kitchen with everything we could want or need. Sharon is the consummate host. We absolutely love being there and our 2 dogs do too! We can't wait for our next visit!!
Private room in Newfane
5 out of 5 average rating, 9 reviews

King bed+private bath, breakfast included

CarolRating, 5 stars28 months ago
I recently spent 3 snowy, quintessentially Vermont days at Thomas & Ravi’s guest house in Newfane, VT. I was given excellent directions & upon arrival Thomas helped heft my heavy ski luggage. This idyllic setting is conveniently located between Brattleboro and Mt. Snow and within a 45 minute drive to Stratton. Would most definitely recommend for a DIY retreat!
Private room in Worthington

The Mountain Room - Goldenrod

BenRating, 5 stars10 months ago
Fantastic to spend some time at the Goldenrod with Aaron and Eric with our two kids and family this weekend. The hospitality was fantastic, location incredible, and we loved the restaurant, our beds, and the 3 goats to feed in the back. Thank guys for hosting us! Can’t wait to return on our next trip to the Berkshires
Superhost
Private room in Kingston

Kingston Carriage House - Drawing Loft

LindaRating, 5 stars7 months ago
This inn was very nicely renovated and appointed. We loved the parking right out front, the front porch in the afternoons and the free snacks in the lounge ;-). We would stay again. A few restaurants on the block are nice and the waterfront area is great for walking and dining and it’s less than a 5 minute walk away.
Superhost
Private room in Guilford
5 out of 5 average rating, 17 reviews

Beautiful B&B room by a river and covered bridge.

ShelleyRating, 5 stars7 months ago
If you want peace and quiet then this was the place. Lee and Bob were wonderful just and breakfast was delicious. We enjoyed a morning walk and getting to know our wonderful host.

Quick stats about bed and breakfast rentals in Lenox

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹6,857 before taxes and fees

  • Total number of reviews

    130 reviews

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

Destinations to explore