Bed and breakfast vacation rentals in Windham County

Find and book unique bed and breakfast rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Windham County bed and breakfast rentals

Family-friendly bed and breakfast rentals

Top guest favorite
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 ❤️
A charming building with an American flag prominently displayed is surrounded by vibrant flower beds. The garden features a variety of colorful blooms, while a well-kept lawn adds to the inviting setting. Nearby, a red barn complements the picturesque landscape.
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!
A welcome sign for Shearer Hill Farm Bed and Breakfast is prominently displayed. The sign features script lettering and is adorned with green garland and red ribbons. Snow is partially visible on the ground, with a gravel road leading into the farm.
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
A quaint lodge is pictured amidst a winter landscape, with snow covering the ground and branches of surrounding trees. Soft light glows from a window, and a sign is visible at the entrance, indicating the welcoming atmosphere of the lodge.
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.
A bright bedroom features a spacious bed dressed in white linens, flanked by two bedside lamps on wooden tables. Natural light filters through two windows covered by light draperies, against a backdrop of green walls and warm wood accents.
Private room in Wilmington

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

Bed and breakfast rentals with breakfast

A natural wooden railing overlooks a scenic view of greenery and a gently flowing river, bordered by trees. The image captures the tranquil setting with a nearby road visible, inviting a sense of peace in a rural environment.
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.
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 stars41 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 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
A rustic living area features exposed wooden beams and a brick fireplace, with a cozy fire burning inside. Deep brown leather sofas surround a low coffee table, and a chandelier hangs overhead, adding a touch of elegance to the warm space.
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.
A well-lit bathroom features a large whirlpool bath positioned under a skylight, providing natural light. A wooden cabinet sits nearby, and sheer white curtains frame the window, which offers a view of surrounding greenery. The clean, neutral walls enhance the serene atmosphere.
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.
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 stars40 months ago
what a lovely stay! rustic inn, super friendly and helpful hosts! we wil be back 💞 thank you!
A view from a wooden deck, featuring a smooth, polished railing. Lush greenery surrounds the area, with trees framing the scene. In the distance, a winding road and a stream are visible, highlighting the natural beauty of the landscape.
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!
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 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

An aerial view captures the estate surrounded by vibrant autumn foliage, showcasing a pond and expansive green space. The colorful trees create a contrast with the white buildings, while the winding road divides the landscape, highlighting a peaceful rural setting.
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 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 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!
Top guest favorite
A spacious bedroom features a four-poster bed dressed in white linens and plush pillows. Two bedside tables with lamps flank the bed. A round mirror hangs above a chair beside a small table, while a plush area rug lies underfoot. Windows are adorned with drapes.
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.
The spacious room features a large bed with crisp white bedding, complemented by two bedside lamps on wooden tables. Natural light floods in through two windows, illuminating the purple walls and hardwood flooring. A small table and chairs are positioned near the windows.
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 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 stars5 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!!
A double twin room features two wooden beds with intricate posts, positioned parallel to each other. Soft white bedding covers the beds, while a patterned area rug enhances the space. Complementary wall sconces provide illumination, and a door leads to the adjoining bathroom.
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