Bed and breakfast vacation rentals in Windham County

Find and book unique bed and breakfast rentals on Airbnb

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Popular amenities for Windham County bed and breakfast rentals

Bed and breakfast rentals with breakfast

Private room in Winhall
5 out of 5 average rating, 3 reviews

Bromley View Inn Suite #12

DanielRating, 5 stars38 months ago
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.
Private room in Wilmington
5 out of 5 average rating, 5 reviews

Apple Hill Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

DonRating, 5 stars33 months ago
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!
Superhost
Private room in Dover
4.97 out of 5 average rating, 38 reviews

Deluxe King, kitchenette,fireplace- Cider House 1

Rebecca ARating, 5 stars4 months ago
My boyfriend and I spent two wonderful nights in Cider House 1. We had a fabulous time. Peaceful and relaxing with beautiful fireplace.
Private room in Wilmington
5 out of 5 average rating, 3 reviews

Wilmington Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

MelissaRating, 5 stars3 days ago
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.
Private room in Wilmington
5 out of 5 average rating, 10 reviews

Chimney Hill Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

LianaRating, 5 stars38 months ago
what a lovely stay! rustic inn, super friendly and helpful hosts! we wil be back 💞 thank you!
Private room in Wilmington
5 out of 5 average rating, 4 reviews

Jennies Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

KatherineRating, 5 stars25 months ago
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

Top guest favorite
Private room in Chester
5 out of 5 average rating, 21 reviews

Farm at Williams River House - Gloucester Suite

DevonRating, 5 stars6 months ago
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!
Private room in Newfane
5 out of 5 average rating, 9 reviews

King bed+private bath, breakfast included

CarolRating, 5 stars27 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!
Guest favorite
Private room in Brattleboro
5 out of 5 average rating, 9 reviews

Purple Chef's cozy lair

JackieRating, 5 stars2 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!!
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 stars5 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.
Top guest favorite
Private room in Chester
5 out of 5 average rating, 21 reviews

Farm at Williams River House - Hawthorne Suite-ADA

MollyRating, 5 stars2 months ago
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!
Private room in Newfane
5 out of 5 average rating, 3 reviews

Queen bed + private bath, breakfast included

SebastianRating, 5 stars19 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!
Superhost
Private room in Guilford
5 out of 5 average rating, 6 reviews

Relaxing private room with bath by the Green River

CarlRating, 5 stars14 months ago
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!

Destinations to explore