
Farmstay holiday rentals in Windsor County
Find and book unique farm-stay accommodation on Airbnb
Top-rated farm-stay accommodation in Windsor County
Guests agree: These farm-stay rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor County farm-stay accommodation
Family-Friendly farm stay rentals

5BR Chalet in Historic Town bet Killington & Okemo
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!

Beautiful Art Studio with hot tub/sauna #1 Airbnb
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!

Cowshed Cabin Farm
Great host, great location. Very relaxing and close to many attractions. Loved watching all the birds coming into the yard

Close to Okemo, 25 Acre Mountain Playground
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

A million-dollar view near Killington on 60 acres.
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

Colonial-style solid-timber home--sanctuary.
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!

Killington Retreat | Deck-Fire Pit-Mountain Views!
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 .

Bill’s Barn Rochester Vermont 3 Bdrm entire house
We loved the open floor plan. Perfect for our family get together. The setting and view was beautiful.
Farm-stay accommodation with a patio

Peace & quiet at Comet Farm
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!

The Creek Cabin at Sky Hollow
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!

500 Acre Farm Retreat: OQ Farm's Priory
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!

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

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

Stylish factory-farmhouse deluxe loft
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!

Cottage in the middle of family horse farm
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!

Brand New Creekside Cabin at Killington
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.
Farmstay rentals with a washing machine and dryer

Vermont Country Paradise minutes from Resorts

Modern Farmhouse on 25 Acres - Superb Views

Stunning Converted Barn Home 3-bed 2 bath

Cottage in the Heart of the Green Mountains

100 Acres Views & Creek near Woodstock/Killington

Garden Retreat, Lake Fairlee, Dartmouth & Ski-way

Quechee Hathaway House: gardens, hot tub & views

Private, 1 bedroom boutique tiny home
Destinations to explore
- Ski-in/ski-out rentals Windsor County
- Rentals with a fire pit Windsor County
- Villa rentals Windsor County
- Apartment rentals Windsor County
- Beachfront rentals Windsor County
- Rentals with pools Windsor County
- Rentals with a washing machine and dryer Windsor County
- Pet-friendly rentals Windsor County
- Rentals with an accessible height bed Windsor County
- Rentals with outdoor seating Windsor County
- Rentals with an EV charger Windsor County
- Cottage rentals Windsor County
- Rentals with a kayak Windsor County
- Kid-friendly rentals Windsor County
- Rentals with breakfast Windsor County
- Fitness-friendly rentals Windsor County
- Waterfront rentals Windsor County
- Rentals with lake access Windsor County
- Rentals with a hot tub Windsor County
- Rentals with a sauna Windsor County
- Condo rentals Windsor County
- Guesthouse rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Rentals with beach access Windsor County
- Tiny house rentals Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
- Rentals with a patio Windsor County
- Townhouse rentals Windsor County
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Family-friendly rentals Windsor County
- Bed and breakfasts Windsor County
- Farmstay rentals Vermont
- Farmstay rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Dorset Field Club
- Fort Ticonderoga
- Autumn Mountain Winery
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Hooper Golf Course
- Bretwood Golf Course
- Brattleboro Ski Hill
- Fox Run Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Things to do Windsor County
- Food and drink Windsor County
- Things to do Vermont
- Food and drink Vermont
- Nature and outdoors Vermont
- Things to do United States
- Entertainment United States
- Wellness United States
- Food and drink United States
- Nature and outdoors United States
- Sports activities United States
- Tours United States
- Art and culture United States
- Sightseeing United States