Bed and breakfast holiday rentals in Lenox

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Popular amenities for Lenox bed and breakfasts

Family-Friendly Bed and Breakfasts

Superhost
Private room in Tivoli
4.9 out of 5 average rating, 125 reviews

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

EmmaRating, 5 stars10 months ago
A Limerick for Tim (a Timerick): Want to chat with the ghost of Kandinsky, Or get drunk with Foucault or Dzierzynski? Gird your loins, take my heed, There’s just one thing you need, Buckle up and book Innski Suminski!
Superhost
Hotel room in Woodstock
4.95 out of 5 average rating, 39 reviews

Room 5 - Second Floor - Twin Gables of Woodstock

JamesRating, 5 stars3 months ago
Great location and well run and put together. Staying again and will do so in the future. Highly recommend.
Top Guest favourite
Private room in North Chatham
4.96 out of 5 average rating, 537 reviews

Charming Eyebrow Colonial North Chatham, NY

LucieRating, 5 stars4 days ago
Susan was a wonderful host! Even if I was out and about the whole weekend, she made herself available when I had questions, provided suggestions for cities to visit around North Chatham. The house is beautiful and peaceful, a heaven for birdwatchers and nature lovers!
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 stars46 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, 121 reviews

Cozy 3 bedroom cape at end of road in Williamstown

CarolineRating, 5 stars1 week ago
Great spot for our son’s graduation. We had the upstairs which gave us privacy and flexibility in case our other son and a cousin could join us. Cozy, clean and comfortable. Charmaine was a warm and gracious hostess. Good coffee in the morning.
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, 779 reviews

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

RhondaRating, 5 stars2 weeks ago
Ilja was wonderful, friendly, and helpful. He was able to accommodate an early check-in so we could prepare for a wedding we needed to attend. Every amenity that you could think of was offered, down to the lint roller and flashlight, and he even asked if we needed anything else. Ilja had fresh coffee available at all times and space offered in kitchen with glasses, water, tea, etc. He was very respectful and helpful. We enjoyed the peaceful areas outside the home, and would have enjoyed sitting by the pond if it had not been raining during our entire stay. We liked the historic character and charm of both the inside and outside of the home. I would highly recommend and will return if in the area again.

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 stars25 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.
Private room in Purling
5 out of 5 average rating, 15 reviews

Family Suite at Shinglekill Falls

EricRating, 5 stars4 months ago
Fantastic stay! Jill is truly the best host we’ve ever had in all our Airbnb experiences. She made us feel so welcome, and we truly appreciated her hospitality. The place was perfect, comfortable, and had everything we needed. We would absolutely love to come back and highly recommend this place to others!
Private room in Goshen
4.91 out of 5 average rating, 99 reviews

Classic New England Bed & Breakfast

AngelaRating, 5 stars8 months ago
Mary’s place is a charming little colonial farmhouse built in the late 1700s out in a beautiful rural part of CT. It is quirky and filled with signs of an earlier time while updated with modern conveniences. It’s not all shiny and new, so if that’s your thing, stay home. But if you want to be charmed with glimpses into the past, be surrounded by gorgeous countryside with parks galore and hiking at every level, and have an imagination that finds inspiration in glimpses of history, then this is your place!
Private room in New Marlborough
5 out of 5 average rating, 4 reviews

The Inn at Freeman Elms Farm B & B- Cottage Room

TrishRating, 5 stars46 months ago
Absolutely beautiful and relaxing setting. The house is so lovely, and well appointed with a wonderful array of antique furnishings and art. The front screened porch was our favorite spot- Anita is the epitome of the hostess extraordinaire. She is friendly and attentive to her guests, but not at all overbearing. Her pride in her family home and history is evident from the moment she greets you. We loved it and would definitely go back. Breakfast was delicious and she looks to everyone detail… down to the doilies on the delicate tea cups. I highly recommend this gem in New Markboriugh. The best of the Berkshires for sure.
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!
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.
Private room in Lee
4.95 out of 5 average rating, 41 reviews

Spacious King BR in Lee

LisaRating, 5 stars71 months ago
Roberta and Bob are very hospitable and make you feel right at home. The room is spacious, private, meticulous, and well-appointed. Breakfast was yummy. The location is very convenient to all the Berkshire events and venues.

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 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
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.
Top Guest favourite
Private room in Rensselaerville
5 out of 5 average rating, 40 reviews

Cozy Queen room in Historic Bed and Breakfast

CmRating, 5 stars3 days ago
We came to town for a friend's birthday party and were recommended to stay at Catalpa House. Ellen was very communicative when our flight was delayed. Upon our arrival, we were shown to an excellent room with a very comfortable bed, pillows, linens, and a well-appointed bathroom. The historic house has beautifully decorated rooms and fresh flowers, well-placed. If you appreciate attention to detail in design, gracious hosts, and gourmet breakfasts, then Catalpa House should be on your list.
Private room in Newfane
5 out of 5 average rating, 3 reviews

Queen bed + private bath, breakfast included

SebastianRating, 5 stars21 months ago
This is an idyllic setting for a beautiful home with super friendly and caring hosts. The large house, a retreat center with facilities for large groups, sits on a lake overlooked by a gorgeous modern treehouse. Tom and Ravi are excellent hosts and I enjoyed chatting and eating with them and learning about their vision for the property, communal and artistic, with nourishing food fresh from local farms, and a mix of interesting guests. This is the kind of place where you can truly unwind in natural green, wander the extensive grounds and connect socially if that suits you. The beds are comfortable, each room with its own bathroom, and the living rooms are spacious and with walls of books and artwork. Cannot recommend this place more highly. If you’re lucky enough to find availability, don’t hesitate!
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 Windsor

Graduation season is around the corner, book now!

ChristineRating, 5 stars7 months ago
Sandra and Tom are amazing hosts. Everything is so cozy and they are incredibly warm and welcoming, it was home away from home! Sandra is an amazing cook and was so accommodating to our individual preferences. Highly recommend and definitely would stay here again!!
Superhost
Private room in Kingston

Kingston Carriage House - Drawing Loft

LindaRating, 5 stars8 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.

Quick stats about bed and breakfast rentals in Lenox

  • Total rentals

    20 properties

  • Nightly prices starting at

    $123 AUD before taxes and fees

  • Total number of reviews

    130 reviews

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

Destinations to explore