Bed and breakfast holiday rentals in Windham County

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Popular amenities for Windham County bed and breakfasts

Family-Friendly Bed and Breakfasts

Top Guest favourite
Private room in Town of Rockingham
5 out of 5 average rating, 123 reviews

Eva Blake House-Margaret's Room

MicahRating, 5 stars1 month ago
This is a very comfortable and pleasant B&B in a well-preserved and beautiful old house--they had a little guide to the history in each room. The beds are very comfortable to sleep in and the temperature in the rooms is nice and warm. Breakfast was delicious. The best thing about it was the hosts: they are very friendly and attentive. You get the impression they really like their guests and enjoy sharing their beautiful home. This place is an absolute gem.
Top Guest favourite
Private room in Putney
4.95 out of 5 average rating, 221 reviews

Sanctuary Garden Bed & Breakfast

ClaudiaRating, 5 stars19 months ago
Caitlin and her husband, Peter, are caring, considerate hosts. They made me feel welcome in their beautifully appointed, light-filled home. They were open and friendly, interested in finding out who I was, while being respectful of my privacy. When I explained I didn't like to eat first thing in the morning, they went out of their way to prepare a yummy, healthy "to-go" breakfast I could take with me to the program I was attending. Caitlin even loaned me her favorite travel coffee mug for my tea. I was able to spend my final morning having breakfast with them and they prepared a delightful meal, replete with fresh fruits and flowers from their garden. We sat outside amongst the beautiful plantings and each shared with me a precious piece of their own life story as well as how they met. That's how I discovered what wonderful people they are. I would return there in a heartbeat. Staying at the Sanctuary provided a welcome contrast from the intensity of the program I was attending.
Top Guest favourite
Private room in Brattleboro
4.91 out of 5 average rating, 102 reviews

The Purple Chef's House

RoiRating, 5 stars5 months ago
Beautiful house and amazing hostess! We both had a great time. Sharon is super friendly and very helpful. Can't wait to come again ❤️
Top Guest favourite
Barn in Guilford
4.99 out of 5 average rating, 119 reviews

The Carriage Barn

KyleRating, 5 stars1 week ago
I stayed at Katherine's during renovations on my house in a nearby town. I appreciated her flexibility and the fact that she also accommodated my dogs as the experience has been challenging for all of us. The location of Katherine's property is easy to find and very close to Brattleboro for most things you would need during your stay.
Top Guest favourite
Private room in Town of Rockingham
5 out of 5 average rating, 74 reviews

Eva Blake House-Eva's Room with One Double Bed

Moss BossRating, 5 stars1 month ago
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!

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 stars32 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 stars3 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, 10 reviews

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

LianaRating, 5 stars37 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 stars24 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 favourite
Private room in Chester
5 out of 5 average rating, 21 reviews

Farm at Williams River House - Gloucester Suite

DevonRating, 5 stars5 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 stars26 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!
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 stars4 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 favourite
Private room in Chester
5 out of 5 average rating, 21 reviews

Farm at Williams River House - Hawthorne Suite-ADA

MollyRating, 5 stars1 month 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 stars18 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!

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