Bed and breakfast holiday rentals in Windsor County

Find and book unique bed & breakfast rentals on Airbnb

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Popular amenities for bed & breakfast rentals in Windsor County

Family-friendly bed & breakfast rentals

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

George's Room - Golden Stage Inn

AshleyRating, 5 stars49 months ago
Julie-Lynn and Mike's place is absolutely wonderful. We had a great weekend stay and couldn't have asked for a better place to stay. The room was clean and comfortable. The breakfasts were delicious and to our surprise chocolate cake on the weekend which was a great treat. We hope to be back again to stay when we are in Vermont.
Private room in Shrewsbury
4.82 out of 5 average rating, 84 reviews

Balm of Gilead B&B - Green Room

LoganRating, 5 stars12 months ago
Sarah is a great host. She even offered to pick us up in case our vehicle couldn't handle the snow. The house is beautiful. We'll be back
Superhost
Private room in Norwich
4.83 out of 5 average rating, 105 reviews

The Partridge House Room 202

JakeRating, 5 stars4 months ago
Ciaran was so kind and his inn was so cute and clean and well managed. We’d absolutely stay again.
Superhost
Private room in Killington
5 out of 5 average rating, 15 reviews

Efficiency Apartment with Queen and Twin over Queen Bunk - The Trailside Inn

WilliamRating, 5 stars26 months ago
Unique place, very enjoyable, and excellent host
Guest favourite
Private room in Shrewsbury
4.96 out of 5 average rating, 53 reviews

Balm of Gilead B & B Blue Suite

Arthur Kwan HungRating, 5 stars12 months ago
nothing but praises for Sarah’s place! Her radiance and hospitality is just so heart warming! This is our group’s second year of staying at Sarah’s and we love it! Looking forward to be back! Love the breakfast Sarah serves - best way to start a ski day. Definitely need to give her jomemade Hollandaise sauce a try!
Superhost
Private room in Norwich
4.88 out of 5 average rating, 86 reviews

The Partridge House Room 203

LukeRating, 5 stars2 weeks ago
Norwich is a quaint small town, with a downtown of pretty much one street. If you are looking for peace and quiet to take in beautiful surroundings, then it is the town to be. The Partridge House is the perfect image of a New England B and B. Old house with old charms and the feeling of being in a home that wants you there. Ciaran is very friendly and makes a great breakfast.
Superhost
Private room in Killington
4.81 out of 5 average rating, 16 reviews

Twin Room with Private Bath - The Trailside Inn

LizRating, 5 stars10 months ago
This place felt like a home away from home! I stayed because I was running a race the next day. Everything was so clean and tidy in the room, and the game room and community area were great places to be, especially if you wanted to commune with other people staying at the inn. It had a community feel, and Joshua was friendly and responsive. He takes pride in his business. I will be back again!
Private room in Proctorsville
4.6 out of 5 average rating, 5 reviews

Cornelia's Room - Golden Stage Inn

TimRating, 5 stars38 months ago
A wonderful bed and breakfast with everything one would expect from a classic Vermont BnB! The hosts made me feel welcomed and right at home. I particularly enjoyed the bedroom with a quaint fireplace and a large shower. Several personal touches with a gift bags of hand warmers, tissue, a snack! A great touch. The breakfast which happened to be my favorite dish which is french toast, it was among the best I have ever had. Will be my go-to lodging anytime I am in the the area!

Bed and breakfast rentals with breakfast

Superhost
Private room in Killington
5 out of 5 average rating, 9 reviews

Queen & Twin Room with Private Bath- Trailside Inn

GiovannaRating, 5 stars14 months ago
This was our second time staying at Trailside and once again it was above our expectations. Check-in/check-out was seamless, the room and Inn were clean and cozy, and Josh provided awesome restaurant recommendations that did not disappoint. Conveniently located to Killington and all the surrounding activity but the best part of our stay was just hanging around the inn. Morning coffee and breakfast was great and hot tea by the fire after a long ski day perfectly capped off the evening. Will definitely be back but only next time we hope to stay for longer.
Superhost
Private room in Killington
4.65 out of 5 average rating, 48 reviews

Standard Queen (Mountain Sports Inn)

AlexRating, 5 stars1 month ago
Perfect location with walking distance to local spots. Clean, quiet and affordable! Will definitely be back.
Superhost
Private room in Killington
4.69 out of 5 average rating, 29 reviews

Premium Queen (Mountain Sports Inn)

MarciRating, 5 stars4 weeks ago
I have a stayed at this place a couple of times, Love how close it is to Killington and the home feel of the place! I enjoyed playing games with my son in the common area. Everyone was super friendly. Was also happy to find 2 beds in the room!
Guest favourite
Private room in Windsor
4.88 out of 5 average rating, 77 reviews

Stay at the largest Colonial Revival Mansion in US

KevinRating, 5 stars2 weeks ago
This stay was absolutely incredible—far exceeding our expectations when all we initially wanted was a convenient location near the ski resorts. From the moment we arrived, we were warmly greeted by the wonderful host, who not only upgraded our room but also offered a fascinating history tour of the mansion. He then offered us drinks at the bar and started a wood fire for us. Andy's hospitality went above and beyond. He arranged an early express breakfast so we could hit the slopes first thing in the morning, and to our surprise, when we woke up, he had already cleared the snow off our car and shoveled the pathway—ensuring a smooth and safe departure. This level of care and attention to detail is truly unmatched. It’s the kind of hospitality that sets the gold standard, and we can’t recommend this place highly enough!
Superhost
Private room in Killington
4.75 out of 5 average rating, 4 reviews

Queen with Twin Bunk Bed - The Trailside Inn

CoreyRating, 5 stars24 months ago
Outstanding host so close to Killington. the complimentary breakfast made my day so easy. The place was clean and quiet The hosts and staff were friendly and knowledgeable. I hope to stay here again in the future.
Superhost
Private room in Killington
4.85 out of 5 average rating, 34 reviews

Standard 3 Twin Beds (Mountain Sports Inn)

AdamRating, 5 stars2 weeks ago
Awesome
Superhost
Private room in Killington
4.89 out of 5 average rating, 61 reviews

Standard 2 Double Beds(Mountain Sports Inn)

RichardRating, 5 stars2 months ago
Our ski crew of 3 couples enjoyed the comfortable common area and hearty brunch. Would recommend highly.
Superhost
Private room in Royalton
4.76 out of 5 average rating, 25 reviews

Romantic Farmhouse Room in BnB with Country Views

MengRating, 5 stars1 month ago
Evelyn is a great host, very friendly and thoughtful. And the cats are so cute! Great location and great farm views.

Bed and breakfast rentals with a patio

Top guest favourite
Private room in Chester
5 out of 5 average rating, 20 reviews

Farm at Williams River House - Gloucester Suite

ElizabethRating, 5 stars5 months ago
Wonderfully relaxing and a perfect fall weekend for my partner and I. We interacted quite a bit with John who was gracious, helpful and a pleasure to be around. He gave us great recommendations and historical facts about the farm and VT. Both Kathy and John were hospitable and made us feel right at home. The property is spacious and offers ample opportunities for connecting with the great outdoors.
Guest favourite
Private room in Woodstock
4.88 out of 5 average rating, 16 reviews

Bedroom in The Bunkhouse

AgnesRating, 5 stars2 months ago
Great stay in the barn at Wise Pines! Chelsea gave super clear instructions and the welcome guide was very helpful! We had a private room which was cozy (especially with the provided space heater) and clean. We appreciated the white noise machine since our room was right next to the shared bathrooms and kitchenette. Overall great place to stay and I'd love to come back and stay for longer!
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 stars4 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 - 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!

Destinations to explore