
Bed and breakfast holiday rentals in Windham County
Find and book unique bed and breakfasts on Airbnb
Top-rated bed and breakfasts in Windham County
Guests agree: These bed and breakfast rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham County bed and breakfasts
Family-Friendly Bed and Breakfasts

Eva's Room/Ensuite bath with One Double Bed
Warmth, humor, history, comfort and delicious food await you at the Eva Blake house. Eileen and Ed are some of the loveliest people you’ll ever meet and embody the warmth of Vermont community and creative culture. They go out of their way to make their guests feel comfortable and delight in sharing their beautiful, pristinely kept Victorian home steeped in history. This is a very special place with special people and I am so grateful to have stayed here a second time. I will be back again soon. Do yourself a favor and visit. Your heart will thank you ❤️

County Carriage House Suite
If I could give Patti and Bill more than 5 stars, I would. This bed & breakfast is such a hidden gem. Patti and Bill are so kind, they make you feel just like family. Their baked apples and breakfast are so delicious, I will miss waking up to them. Their home has a way of making you feel like its your own home, and there’s such rich history all around the house. The carriage house was a great stay for a small group of friends who were looking for lodging for our Mt. Snow ski trip. The rooms and beds were so cozy and we had some of the best sleep of our lives! The mountain was a short 20 min drive. The town of Wilmington is so cute and a short drive away as well. Patti recommended some local eats which we appreciated. There’s so much more we want to see and do at this bed and breakfast and will surely return in the Spring or Summer!

Baked Apples At Shearer Hill Farm B&B Room 2
The Shearer Hill Farm is not only a cozy and beautiful place to stay at, it also has the best hosts, Patricia and Bill. Their attention to detail, kindness and hospitality made this a fantastic experience. Breakfast here was worthy of a 5 star restaurant, their coffee and jams were sooo good too. Our rooms was beautifully decorated, also super comfy and clean. Thanks for having us so last minute! Hope to be back soon. :)

Family Room at The Upper Pass Lodge
Our family enjoyed our stay. The area was beautiful. The room was as described and clean. The staff was super friendly and very accommodating! We ate both supper and breakfast there and both meals were delicious. We would definitely visit again.

Joseph Courtemanche Suite @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!
Bed and breakfast rentals with breakfast

Betty's Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!
This is a lovely place and space! Cozy, comfortable, clean and simple style, Charlie & Megan go the extra mile to make sure your stay is comfortable and you have everything you need. They communicate before and during your trip and help with anything you need. They are COVID conscious and we felt very comfortable and safe with the measures they put in place. Oh, and the breakfast menu is delicious and they have an amazing cocktail list perfect for winding down at the end of the day.

Bromley View Inn Suite #12
The inn is in a great location, close to both Stratton and Bromley. Austin was quick to communicate with, check-in was easy, room was clean and comfortable, and breakfast in the morning was great - eggs and bacon, muffins, waffles, etc.

Apple Hill Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!
The Wilmington Inn is always a favorite place to stay! It's always quiet and so convenient to restaurants and the shops--we'll be back!

Deluxe King, kitchenette,fireplace- Cider House 1
My boyfriend and I spent two wonderful nights in Cider House 1. We had a fabulous time. Peaceful and relaxing with beautiful fireplace.

Molly Stark Suite @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!
Excellent stay! Breakfast every morning was delicious. Walking distance to several restaurants and only a 15 minute drive to Mt Snow. Charlie and Megan were great and always available.

Chimney Hill Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!
what a lovely stay! rustic inn, super friendly and helpful hosts! we wil be back 💞 thank you!

Windham Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!
Cute mountain farmhouse theme Bed, and Breakfast. If you are looking to fully emerge in the Vermont experience-this is it. We enjoyed cozying up next to the woodstove in the living room/dining room while the host served us some drinks (all while feeling safe with everyone respecting COVID guidelines). Great trip!

Jennies Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!
This is an easy place to stay. Breakfast was great. The hosts are around and helpful. Beautiful house.
Bed and breakfast rentals with a patio

King bed+private bath, breakfast included
The hosts are extremely hospitable. Place was clean, cozy, comfortable and inviting. Included breakfast was fantastic and hearty. Also loved the resident cat who was seen on a few occasions. Loved it and will absolutely be back when in the area.

Farm at Williams River House - Essex Suite
This was my first Airbnb experience. From the very beginning, John and Kathy were excellent hosts. They come across as just genuine and likeable people - it really feels like you’re staying with friends. Not to mention, they are SO kind in opening up their entire (gorgeous) home and property to you. They make it clear that while you’re there you have free range to explore the grounds or utilize the fun on-site things such as the fire pit and relaxing common areas. The breakfast served each morning was so thoughtful and delicious; my husband and I really felt like we were being spoiled!! Speaking of spoiled, idk how I’ll ever be able to have a better Airbnb experience than John and Kathy provided as they really set the bar high. Looking forward to booking our next visit here for sure.

Farm at Williams River House - Gloucester Suite
I absolutely loved our stay here - so much so that I’m currently looking at a calendar to see when we can come back! The beauty of the landscape, nice rooms/house and hospitality felt like a true treat!

King bed+private bath, breakfast included
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!

Purple Chef's cozy lair
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!!

Yogi & artist retreat center
Thomas has a beautiful yoga retreat type of resort up in the mountains of Vermont. The place is stunning. The rooms are very comfortable and they give you a delicious breakfast. It's definitely worth the time and money to stay with Thomas. 5 star rating. I hope to come again with my family.
Destinations to explore
- Rentals with a kayak Windham County
- Rentals with a hot tub Windham County
- Beachfront rentals Windham County
- Rentals with pools Windham County
- Kid-friendly rentals Windham County
- Waterfront rentals Windham County
- House rentals Windham County
- Rentals with outdoor seating Windham County
- Rentals with beach access Windham County
- Rentals with a fireplace Windham County
- Rentals with a patio Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with lake access Windham County
- Chalet rentals Windham County
- Cabin rentals Windham County
- Rentals with an accessible height toilet Windham County
- Rentals with a fire pit Windham County
- Family-friendly rentals Windham County
- Rentals with a sauna Windham County
- Pet-friendly rentals Windham County
- Condo rentals Windham County
- Tiny house rentals Windham County
- Rentals with an EV charger Windham County
- Apartment rentals Windham County
- Fitness-friendly rentals Windham County
- Rentals with a washing machine and dryer Windham County
- Private suite rentals Windham County
- Farmstay rentals Windham County
- Rentals with breakfast Windham County
- Townhouse rentals Windham County
- Bed and breakfasts Vermont
- Bed and breakfasts United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club
- Bretwood Golf Course