Bed and breakfast vacation rentals in Windham County

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Popular amenities for Windham County bed and breakfast rentals

Bed and breakfast rentals with breakfast

Four wooden Adirondack chairs surround a fire pit, with a warm flame glowing in the center. The backdrop features a snow-covered landscape and Bromley Mountain in the distance, under a cloudy sky. Snow blankets the ground, creating a serene outdoor setting.
Private room in Winhall
5 out of 5 average rating, 3 reviews

Bromley View Inn Suite #12

DanielRating, 5 stars39 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.
A wooden railing extends along the deck, offering a view of the surrounding greenery and the nearby road. Lush foliage and trees frame the scene, while the distant outline of hills is visible in the background.
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 stars34 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
A spacious living area features rustic wooden beams and large windows, allowing natural light to fill the room. Comfortable leather sofas surround a wooden coffee table, with an elegant lamp in one corner. A dining area with a large table is visible in the background.
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.
A wooden railing borders a deck, providing a view of a winding road and lush greenery. The landscape is framed by trees, with hints of a river visible in the distance, creating a natural connection to the surrounding environment.
Private room in Wilmington
5 out of 5 average rating, 3 reviews

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

MelissaRating, 5 stars2 weeks 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.
A wooden railing features a natural finish, offering a clear view of the lush greenery surrounding the area. Beyond the railing, the road can be seen winding through the landscape, with trees framing the scene and a gentle slope leading to a stream.
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!
An outdoor deck features a natural wood railing that offers a view of the lush greenery and flowing river below. The surrounding trees provide a serene backdrop, creating a peaceful atmosphere for relaxation.
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
A cozy bedroom features a spacious bed adorned with a soft white duvet and decorative pillows. Elegant wooden nightstands with lamps flank the bed, while light streams through partially open window treatments, illuminating the soft blue and patterned wallpaper.
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!
A covered porch with a glass-top table and eight decorative chairs invites outdoor dining. Rocking chairs line the edges, and the lush green yard extends into the background, framed by trees and a distant structure.
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
A cozy bedroom features a queen size bed with floral bedding and decorative pillows. Soft lighting is provided by two bedside lamps. A wooden nightstand is positioned next to the bed, and framed artwork adorns the walls. A patterned area rug adds warmth to the space.
Private room in Brattleboro
5 out of 5 average rating, 9 reviews

Purple Chef's cozy lair

JackieRating, 5 stars3 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
A private bedroom features light purple walls and is illuminated by natural light from multiple windows. A spacious bed is paired with a decorative mirror and a dresser. Two chairs and a small table create a cozy seating area, with an en-suite 3/4 bath visible nearby.
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
A well-appointed bedroom features a spacious bed adorned with soft linens and additional pillows. A stylish vanity with a mirror and a black antique trunk are visible, alongside a window with light-filtering curtains. Decorative wall art complements the floral wallpaper.
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!
A cozy queen room features a wooden bed with a plaid blanket. Two artworks hang on the teal wall, complemented by matching wooden nightstands. Soft lighting is provided by a lamp on one side, while natural light enters through an unseen window.
Private room in Newfane
5 out of 5 average rating, 3 reviews

Queen bed + private bath, breakfast included

SebastianRating, 5 stars20 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
A spacious bedroom is highlighted by warm tones and natural light. A large bed is adorned with colorful pillows, and a wooden coffee table complements the decor. Soft furnishings and large windows create an inviting atmosphere, while light fixtures add a touch of charm.
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