
Bed and breakfast vacation rentals in Windham County
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Top-rated bed and breakfast rentals in Windham County
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Family-friendly bed and breakfast rentals

Eva's Room/Ensuite bath with One Double Bed
Wonderfully kept historic house! We stayed a night to be close to the mountains and the hosts were wonderful and very nice. The bed was was super comfy and the claw foot bath tub is a must for anyone who has never been in one! The breakfast was fantastic and the hosts cooking and table setting were far above average. Would surely stay again!

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. :)
Bed and breakfast rentals with breakfast

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.

Wilmington Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!
I can’t say enough good things about this place. From the moment we arrived, everything exceeded expectations. The inn was spotless, beautifully decorated, and had every amenity we could have needed—and then some. The bed was super comfortable, the view was stunning, and every little detail was clearly thought out with care. The host was incredibly warm, responsive, and welcoming. They went above and beyond to make our stay special, offering great local recommendations and making us feel truly at home. We’ve stayed at a number of places, but this one stands out as one of the best. If you’re considering booking—do it! You won’t regret it. We’re already planning our return trip.

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!

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

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!!

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

Farm at Williams River House - Hawthorne Suite-ADA
We had a wonderful stay at John and Kathy’s farmhouse! Great location for a peaceful retreat and close to several mountains for skiing. John’s breakfast was a fantastic start to each day. They were extremely knowledgeable and helpful regarding things to do in the area. We hope to be back again!

Queen bed + private bath, breakfast included
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!

Relaxing private room with bath by the Green River
Can we give more than 5 stars? Lee and Bob were wonderful hosts and we truly enjoyed their company. Their place was so beautiful and peaceful and the amazing breakfast was just the icing on the cake! Already looking forward to our next visit!
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Berkshire East Mountain Resort
- Monadnock State Park
- Saratoga Race Course
- Bousquet Mountain Ski Area
- Mount Sugarloaf State Reservation
- Mount Snow Ski Resort
- Mount Sunapee Resort
- National Museum of Racing and Hall of Fame
- Peebles Island State Park
- Clarksburg State Park
- Stump Sprouts Ski Touring Center
- Pineridge Cross Country Ski Area
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Bromley Mountain Ski Resort
- Mount Greylock Ski Club
- Willard Mountain
- Dorset Field Club
- Hancock Shaker Village
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