300+ stays

Stays in Windsor County

SUPERHOST
Entire guest suite in Brownsville/West Windsor
Cozy Guest Suite in Charming Farmhouse
2 guests1 bedroom1 bed1.5 bathrooms
WifiFree parking
₹9,417 per night
SUPERHOST
Entire guest house in Springfield
Connecticut River-Cozy Cottage
2 guestsStudio1 bed1 bathroom
WifiFree parkingKitchenAir conditioning
₹6,481 per night
SUPERHOST
Entire rental unit in Andover
Private Hilltop farm apartment
4 guests1 bedroom1 bed1 bathroom
WifiFree parkingKitchen
₹7,333 per night
SUPERHOST
Entire apartment in Ludlow
All Season Lovely and Zen Okemo Mt Lodge Condo
4 guests1 bedroom2 beds1 bathroom
WifiFree parkingKitchen
₹7,221 per night
Entire cabin in Cavendish
Hot Tub Cabin in the Woods
8 guests3 bedrooms4 beds2 bathrooms
WifiFree parkingKitchen
₹16,782 per night
SUPERHOST
Private room in Windsor
Weaving Dreams Farm and Boutique
4 guests1 bedroom3 beds1 private bathroom
WifiFree parking
₹6,997 per night
SUPERHOST
Entire rental unit in Clarendon
Dog heavenly! Private, beautiful and relaxing.
2 guests1 bedroom0 beds1 bathroom
WifiFree parkingKitchenAir conditioning
₹6,029 per night
SUPERHOST
Entire loft in Ludlow
Spacious Renovated Barn Apt on 100 acres!
6 guests2 bedrooms2 beds1 bathroom
WifiFree parkingKitchenAir conditioning
₹15,203 per night
SUPERHOST
Farm stay in Plainfield
Renovated 1817 Hobby Farm Close to Dartmouth
4 guests1 bedroom3 beds1 bathroom
WifiFree parkingKitchenAir conditioning
₹8,101 per night
SUPERHOST
Entire guest house in Hartland
Yurt In The Woods - Private Refuge
6 guests1 bedroom3 beds1 bathroom
WifiFree parkingKitchen
₹11,784 per night
Entire cabin in Ludlow
Beautiful lake cottage close to Okemo Mt
5 guests2 bedrooms4 beds1 bathroom
WifiFree parkingKitchen
₹13,562 per night
Entire cabin in Cavendish
Copper Hill House - VT getaway near Ludlow & Okemo
6 guests3 bedrooms3 beds2 bathrooms
WifiFree parkingKitchenAir conditioning
₹18,553 per night
SUPERHOST
Entire guest house in Reading
Peaceful Alpine Cottage Retreat with Mountain View
4 guestsStudio3 beds1 bathroom
WifiFree parking
₹11,047 per night
SUPERHOST
Entire rental unit in Chester
Beautiful 2 Bedrooms in Mountains w/ full kitchen
4 guests2 bedrooms4 beds2 bathrooms
WifiFree parkingKitchenAir conditioning
₹9,785 per night
SUPERHOST
Entire residential home in Plymouth
BEST OF LAKE FRONT LIVING, HOT TUB & FIREPIT !!
6 guests2 bedrooms5 beds2 bathrooms
WifiFree parkingKitchen
₹21,832 per night
SUPERHOST
Entire residential home in Cavendish
25 Acre Mountain Playground, Okemo Valley
5 guests2 bedrooms3 beds1 bathroom
WifiFree parkingKitchenAir conditioning
₹12,542 per night
SUPERHOST
Entire cottage in Woodstock
2 person SunCottage - Hot Tub Solar Geothermal
2 guests1 bedroom1 bed1 bathroom
WifiFree parkingKitchenAir conditioning
₹20,254 per night
SUPERHOST
Entire townhouse in Killington
Trailside Townhouse, Ski in/out/Mountain Views
6 guests4 bedrooms8 beds4 bathrooms
WifiFree parkingKitchen
₹9,574 per night
Entire residential home in Cavendish
Four Season River Retreat: Private beaches & more!
8 guests4 bedrooms5 beds2 bathrooms
WifiFree parkingKitchen
₹18,412 per night
SUPERHOST
Entire cabin in Plymouth
Log Cabin@ Lake Ninevah w/ beach, canoes & kayaks
6 guests3 bedrooms4 beds2 bathrooms
WifiFree parkingKitchen
₹13,257 per night
21 – 40 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.