Bed and breakfast holiday rentals in Windham County

Find and book unique bed and breakfasts on Airbnb

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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, 75 reviews

Eva's Room/Ensuite bath with One Double Bed

ErinRating, 5 stars1 month ago
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 ❤️
Private room in Halifax

County Carriage House Suite

LieselleRating, 5 stars16 months ago
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!
Private room in Halifax
4.91 out of 5 average rating, 23 reviews

Baked Apples At Shearer Hill Farm B&B Room 2

LauraRating, 5 stars27 months ago
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. :)
Superhost
Private room in Londonderry
4.67 out of 5 average rating, 24 reviews

Family Room at The Upper Pass Lodge

LeahRating, 5 stars1 month ago
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.
Private room in Wilmington

Joseph Courtemanche Suite @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

Bed and breakfast rentals with breakfast

Private room in Wilmington
5 out of 5 average rating, 5 reviews

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

CherylRating, 5 stars54 months ago
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.
Private room in Winhall
5 out of 5 average rating, 3 reviews

Bromley View Inn Suite #12

DanielRating, 5 stars40 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 stars35 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 stars6 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

Molly Stark Suite @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

TaraRating, 5 stars52 months ago
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.
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 stars40 months ago
what a lovely stay! rustic inn, super friendly and helpful hosts! we wil be back 💞 thank you!
Private room in Wilmington

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

KateRating, 5 stars54 months ago
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!
Private room in Wilmington
5 out of 5 average rating, 4 reviews

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

KatherineRating, 5 stars27 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

Private room in Newfane

King bed+private bath, breakfast included

Nike Rating, 5 stars32 months ago
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.
Top Guest favourite
Private room in Chester
5 out of 5 average rating, 39 reviews

Farm at Williams River House - Essex Suite

Jenna GlindmyerRating, 5 stars7 months ago
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.
Top Guest favourite
Private room in Chester
5 out of 5 average rating, 21 reviews

Farm at Williams River House - Gloucester Suite

DevonRating, 5 stars8 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 stars29 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 favourite
Private room in Brattleboro
5 out of 5 average rating, 9 reviews

Purple Chef's cozy lair

JackieRating, 5 stars4 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!!
Private room in Newfane
4.82 out of 5 average rating, 11 reviews

Yogi & artist retreat center

JoshRating, 5 stars20 months ago
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