Farmstay holiday rentals in Windsor County

Find and book unique farm-stay accommodation on Airbnb

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Popular amenities for Windsor County farm-stay accommodation

Family-Friendly farm stay rentals

Superhost
Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars2 months ago
We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!
Superhost
Cabin in Londonderry
4.76 out of 5 average rating, 405 reviews

Beautiful Art Studio with hot tub/sauna #1 Airbnb

Bari Rating, 5 stars4 days ago
We had a wonderful time in this beautiful rural Vermont oasis. Exactly what we were looking for! The place is quintessential VT…. So if you are looking to spend a few nights in a reconverted barn on farmland…. Well, this is it. We loved being able to walk the property, and the jacuzzi and sauna were a real highlight. Directions getting in and figuring out our building were a bit confusing at first but we figured it out. We had a few small issues but Ben was responsive and did his best to take care of them quickly - with varying levels of success. The outdoor area could use some easier access and a bit more attention, but we were told that it is in the works. We would stay again in a heartbeat!
Guest favourite
Cabin in West Windsor
4.96 out of 5 average rating, 144 reviews

Cowshed Cabin Farm

JefferyRating, 5 stars2 days ago
Great host, great location. Very relaxing and close to many attractions. Loved watching all the birds coming into the yard
Guest favourite
Home in Cavendish
4.94 out of 5 average rating, 81 reviews

Close to Okemo, 25 Acre Mountain Playground

MichaelRating, 5 stars5 months ago
A beautiful place with an incredible view of the mountains- cozy and warm and extra comfy beds! Sheryl’s kitchen had everything we needed. And close to okemo
Guest favourite
Home in Pittsfield
4.85 out of 5 average rating, 106 reviews

A million-dollar view near Killington on 60 acres.

Debbie LynnRating, 5 stars3 months ago
Perfect location for us and what we can to Pittsfield for. We had plenty of room for five of us. Nice to have a bedroom for everyone. Kitchen was equipped to do anything we wanted to as far as cooking etc Close to skiing Loved being on 60 acres. All worked out perfect for all of us
Superhost
Home in Barnard
5 out of 5 average rating, 69 reviews

Colonial-style solid-timber home--sanctuary.

Erin Rating, 5 stars25 months ago
Another stay in the books at Starry Hill! We love this house, peaceful surroundings and lots to do in the area. Heidi and Robert are wonderful hosts, friendly, responsive and will help if you need anything. Memories made in this house!
Guest favourite
Home in Clarendon
4.96 out of 5 average rating, 296 reviews

Killington Retreat | Deck-Fire Pit-Mountain Views!

StephanieRating, 5 stars4 days ago
beautiful white pine floors and cabinets, comfortable feeling as soon as you walk through the door. can see neighbors horses and hear them in the morning to relax to. Great nature light due to the amount and type of windows. we had a very relaxed wedding week off here. 5 minutes from Rutland, vt so quick to go out .
Guest favourite
Home in Rochester
4.97 out of 5 average rating, 98 reviews

Bill’s Barn Rochester Vermont 3 Bdrm entire house

RichardRating, 5 stars3 weeks ago
We loved the open floor plan. Perfect for our family get together. The setting and view was beautiful.

Farm-stay accommodation with a patio

Top Guest favourite
Guesthouse in Reading
5 out of 5 average rating, 30 reviews

Peace & quiet at Comet Farm

XiangchengRating, 5 stars3 months ago
This is an absolutely gorgeous place to stay in Vermont and we loved it!! The living room and bedrooms are all elegantly decorated and also very cozy. More importantly, Madeline and Parris are the best hosts we have ever had. We came to Vermont for a ski trip and ran into some snow-related issues on our first day. Madeline and Parris were very responsive and offered tremendous help to us. Overall, a beautiful house with great hosts for an amazing stay!
Guest favourite
Cabin in Rochester
4.93 out of 5 average rating, 27 reviews

The Creek Cabin at Sky Hollow

AnnaRating, 5 stars1 month ago
The stay was fantastic. The cabin is located in a perfect area surrounded by the woods, beautiful trails, a sauna and just so much greenery we couldn't believe it. The cabin itself was incredibly well put together, had everything you'd need and then some. Jess was very accommodating and answered every question we had. 100% recommend!
Guest favourite
Cabin in Bridgewater
4.98 out of 5 average rating, 51 reviews

500 Acre Farm Retreat: OQ Farm's Priory

KeriRating, 5 stars1 month ago
If you are aiming to book an experience, more than just a traditional stay, do not hesitate and book now! We traveled to OQ Farm with our three daughters (my 8 year-olds request!) and it was an incredible experience being part of the farm and exploring the property. Accommodations were spacious, clean and well appointed. The hosts (and children) are approachable, kind and felt being amongst old friends! There were tears as we left. We have already recommended OQ Farm to family and friends. And our daughters are planning their return to the farm! Unforgettable!
Guest favourite
Cabin in Chittenden
4.96 out of 5 average rating, 112 reviews

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

JessicaRating, 5 stars2 days ago
Such a beautiful and comfortable place for our group to stay at. The beds were super comfortable, it was very relaxing. We spent time enjoying the hot tub and fire pit as well. Came in for a wedding at the Mountaintop Resort, with that being a 6 minute drive, we had nothing to worry about with time. There is a cute general store a couple mins up the road and Rutland isn't far for bigger needs. Nicole was very proactive on giving us all the instructions we needed to check in and plenty of recommendations for the area. There are little gems in the house that were hidden in plain site which added to the charm. Overall, this was a fantastic experience and I absolutely would stay at their property again!!
Top Guest favourite
Home in Windsor
4.99 out of 5 average rating, 94 reviews

Stylish Ascutney Cabin •View •Chef’s Kitchen •Pets

AmandaRating, 5 stars1 week ago
We had a great stay! The house was well-appointed and comfortable. We especially loved the covered porch and beautiful view. It was a great home base for exploring the area, including several nearby hiking trails, Woodstock and Quechee (about a half hour away), and Brattleboro (less than an hour away). Ab was a fantastic host. He was proactive with communication and even checked in with us to make sure we had power after some strong thunderstorms that had moved through the area.
Guest favourite
Loft in Randolph
4.94 out of 5 average rating, 97 reviews

Stylish factory-farmhouse deluxe loft

ErikaRating, 5 stars3 weeks ago
This is such a beautiful AirBnB! The space is comfortable, clean, cozy and beautifully done. It is a great place for families or a group of friends to stay. The beds were amazing and all of the little thoughtful touches and amenities didn’t go unnoticed. While we didn’t get to use the outside because of weather, it was as pictured and I’m sad we were able to use such a cool space with a beautiful stream flowing by. Highly recommend!
Top Guest favourite
Home in Royalton
5 out of 5 average rating, 20 reviews

Cottage in the middle of family horse farm

HeidiRating, 5 stars3 days ago
We really enjoyed our five nights at the Hop House. The place is exactly how it is described/pictured. It isn’t super fancy, but it has a cozy charm that made us immediately feel at home. The back deck is built around a couple of trees! It feels like a treehouse, and from there you can enjoy views of the horses in the pastures and a few cows across the street! The kitchen was well stocked and Dorothy left us coffee and a little bottle of maple syrup! We enjoyed our visit and would definitely stay again!
Guest favourite
Cabin in Killington
4.93 out of 5 average rating, 60 reviews

Brand New Creekside Cabin at Killington

AndrewRating, 5 stars3 weeks ago
Ideal spot within a short walk of the Appalachian Trail, Thundering Brook falls, Kent pond. Can MTB straight to base camp and sherburne trails. Have been looking forward to staying here for a long time. Huge space, very open yet cozy. Porch overlooking the river and marsh is expansive and covered. Breeze means no bugs. Loved our time here.

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