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Top cities in Windsor County

Woodstock
Our top choices for Windsor County holiday rentals

1. Fat Sheep Farm & Cabins
Fat Sheep Farm & CabinsWindsor
9.8 out of 10, Exceptional, (17 reviews)
The price is £134
includes taxes & fees
17 Nov - 18 Nov

2. Addie's Place: A Quiet and Quirky Guesthouse
Addie's Place: A Quiet and Quirky GuesthouseHartford
9.6 out of 10, Exceptional, (23 reviews)
The price is £167
includes taxes & fees
15 Nov - 16 Nov

3. Bridgewater Living - Ben&Jerry Suite
Bridgewater Living - Ben&Jerry SuiteBridgewater
10.0 out of 10, Exceptional, (1 review)
The price is £158
includes taxes & fees
15 Nov - 16 Nov

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)
The price is £205
includes taxes & fees
16 Nov - 17 Nov

5. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails
Cozy Resort Cabin! Hot-Tub Sauna Fire Pit TrailsCavendish
10.0 out of 10, Exceptional, (59 reviews)
The price is £297
includes taxes & fees
15 Nov - 16 Nov

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 DeckHartford
9.2 out of 10, Wonderful, (9 reviews)
The price is £386
includes taxes & fees
15 Nov - 16 Nov

7. Cabin on the hill Ascutney Vt - 4 bedrooms
Cabin on the hill Ascutney Vt - 4 bedroomsWest Windsor
10.0 out of 10, Exceptional, (1 review)
The price is £378
includes taxes & fees
16 Nov - 17 Nov

8. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
Renovated Vermont Retreat with mountain views near Okemo & Killington for 6Cavendish
10.0 out of 10, Exceptional, (4 reviews)
The price is £419
includes taxes & fees
15 Nov - 16 Nov

9. Game Room, Fire Pit & Views! Spacious Ludlow Home
Game Room, Fire Pit & Views! Spacious Ludlow HomeLudlow
The price is £598
includes taxes & fees
15 Nov - 16 Nov

10. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8Hartford
10.0 out of 10, Exceptional, (3 reviews)
The price is £601
includes taxes & fees
17 Nov - 18 Nov

11. Pet Friendly | Game Room | Minutes to Woodstock and Killington
Pet Friendly | Game Room | Minutes to Woodstock and KillingtonBridgewater
10.0 out of 10, Exceptional, (4 reviews)
The price is £386
includes taxes & fees
15 Nov - 16 Nov

12. Cozy Village Condo-Okemo Shuttle
Cozy Village Condo-Okemo ShuttleLudlow
9.8 out of 10, Exceptional, (89 reviews)
The price is £187
includes taxes & fees
15 Nov - 16 Nov

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

14. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski ResortCavendish
10.0 out of 10, Exceptional, (26 reviews)
The price is £375
includes taxes & fees
15 Nov - 16 Nov

15. Gnome Home Mountain Ski Chalet w/Sauna Killington
Gnome Home Mountain Ski Chalet w/Sauna KillingtonStockbridge
10.0 out of 10, Exceptional, (7 reviews)
The price is £352
includes taxes & fees
15 Nov - 16 Nov

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 ShuttleLudlow
9.8 out of 10, Exceptional, (114 reviews)
The price is £398
includes taxes & fees
22 Nov - 23 Nov

17. Village Fireplace Shuttle Boot Warmers
Village Fireplace Shuttle Boot WarmersLudlow
9.8 out of 10, Exceptional, (109 reviews)
The price is £306
includes taxes & fees
30 Nov - 1 Dec

18. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
4-Season Vermont Cabin · 12 Acres, Mountain Views · OkemoChester
10.0 out of 10, Exceptional, (6 reviews)
The price is £696
includes taxes & fees
15 Nov - 16 Nov

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)
The price is £779
includes taxes & fees
15 Nov - 16 Nov

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)
The price is £992
includes taxes & fees
15 Nov - 16 Nov
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.
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