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Top cities in Windsor County

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Our top choices for Windsor County holiday rentals

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (17 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
The price is £134
includes taxes & fees
17 Nov - 18 Nov
Fat Sheep Farm & Cabins

2. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (23 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is £167
includes taxes & fees
15 Nov - 16 Nov
Addie's Place: A Quiet and Quirky Guesthouse

3. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is £158
includes taxes & fees
15 Nov - 16 Nov
Bridgewater Living - Ben&Jerry Suite

4. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (16 reviews)
"Our stay in this tiny home was perfect! Very cozy and private. The host was very responsive and everything was exactly as described."
United States
Kat V.
The price is £205
includes taxes & fees
16 Nov - 17 Nov
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

5. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails
Cavendish
10.0 out of 10, Exceptional, (59 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
The price is £297
includes taxes & fees
15 Nov - 16 Nov
Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

6. 180-degree panoramic views of Vermont's mountains from the living room and Deck

180-degree panoramic views of Vermont's mountains from the living room and Deck
Hartford
9.2 out of 10, Wonderful, (9 reviews)
"Communication was great! The views from the house were terrific and the living room space is really nice."
United States
Craig K.
The price is £386
includes taxes & fees
15 Nov - 16 Nov
180-degree panoramic views of Vermont's mountains from the living room and Deck

7. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
10.0 out of 10, Exceptional, (1 review)
"The Cabin in the Woods looks very rustic on the outside, but a cabin ine the woods should. Inside was a pleasant surprise. Full kitchen, large leather wrap around sofa to watch the LARGE flat-screen TV, large dining room table, 4 bedrooms, and 2 full baths made this a perfect get away place."
United States
Alvin
The price is £378
includes taxes & fees
16 Nov - 17 Nov
Cabin on the hill Ascutney Vt - 4 bedrooms

8. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
Cavendish
10.0 out of 10, Exceptional, (4 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is £419
includes taxes & fees
15 Nov - 16 Nov
Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

9. Game Room, Fire Pit & Views! Spacious Ludlow Home

Game Room, Fire Pit & Views! Spacious Ludlow Home
3.0 star property
Ludlow
The price is £598
includes taxes & fees
15 Nov - 16 Nov
Game Room, Fire Pit & Views! Spacious Ludlow Home

10. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Hartford
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful and well appointed abode - super cozy!"
United States
Nina S.
The price is £601
includes taxes & fees
17 Nov - 18 Nov
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

11. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (4 reviews)
"We loved the farmhouse. It was very charming and cozy. Plenty of space for us and exactly as advertised. We would definitely stay here again. Thank you"
United States
Lisa G.
The price is £386
includes taxes & fees
15 Nov - 16 Nov
Pet Friendly | Game Room | Minutes to Woodstock and Killington

12. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"simple, sweet, CLEAN and easy"
United States
walter s.
The price is £187
includes taxes & fees
15 Nov - 16 Nov
Cozy Village Condo-Okemo Shuttle

13. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is £541
includes taxes & fees
15 Nov - 16 Nov
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

14. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (26 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is £375
includes taxes & fees
15 Nov - 16 Nov
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

15. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (7 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is £352
includes taxes & fees
15 Nov - 16 Nov
Gnome Home Mountain Ski Chalet w/Sauna Killington

16. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
The price is £398
includes taxes & fees
22 Nov - 23 Nov
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

17. Village Fireplace Shuttle Boot Warmers

Village Fireplace Shuttle Boot Warmers
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
The price is £306
includes taxes & fees
30 Nov - 1 Dec
Village Fireplace Shuttle Boot Warmers

18. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is £696
includes taxes & fees
15 Nov - 16 Nov
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

19. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is £779
includes taxes & fees
15 Nov - 16 Nov
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

20. 150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Bethel
9.6 out of 10, Exceptional, (4 reviews)
"5 bedrooms with only 2.5 baths but beautiful!"
United States
Jamie R.
The price is £992
includes taxes & fees
15 Nov - 16 Nov
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find holiday rentals that suit your style

Top Windsor County Hotel Reviews

Find out more about Windsor County

Everything you need to know about Windsor County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Windsor County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor County holiday rentals we have selected for you start as low as £133 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor County rentals

At Expedia, we put the best Windsor County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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