House
10.0(252 Reviews)
2 Bedrooms
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
CA $261/Night
7 Nights - CA $1,830
Windsor County Villa Rentals
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Compare Villas, Resorts, & Rentals in Windsor County
10.0
CA $503/Night
7 Nights - CA $3,521
Bed & Breakfast
10.0(54 Reviews)
1 Bedroom
Hot Tub
Breakfast- Parking
- Balcony/Terrace
CA $463/Night
7 Nights - CA $3,243
House
10.0(82 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
Internet
CA $454/Night
7 Nights - CA $3,176
House
10.0(3 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
Pool- Balcony/Terrace
CA $1,426/Night
7 Nights - CA $9,984
Ski Chalet
10.0(75 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
Spa- Balcony/Terrace
CA $628/Night
7 Nights - CA $4,399
Cabin
10.0(75 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
CA $308/Night
7 Nights - CA $2,157
Apartment
10.0(71 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $536/Night
7 Nights - CA $3,751
House
10.0(68 Reviews)
2 Bedrooms
4 Guests
- Parking
Skiing- Balcony/Terrace
- Kitchen
CA $831/Night
7 Nights - CA $5,813
Luxury Places to Stay in Windsor County
Over 2375+ Luxury Places to Stay in or Near Windsor County
House
10.0(35 Reviews)
15 Bedrooms
46 Guests
Private Pool- Hot Tub
- Breakfast
- Parking
CA $7,606/Night
7 Nights - CA $53,242
House
16 Bedrooms
39 Guests
- Internet
Child Friendly
Security/Safety
CA $6,839/Night
7 Nights - CA $47,874
House
10.0(3 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Pool
- Skiing
CA $5,178/Night
7 Nights - CA $36,248
House
10.0(9 Reviews)
7 Bedrooms
14 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $5,089/Night
7 Nights - CA $35,623
New
Condo
10.0(14 Reviews)
2 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Skiing
CA $5,046/Night
7 Nights - CA $35,323
CA $4,154/Night
7 Nights - CA $29,080
House
10.0(1 Review)
6 Bedrooms
16 Guests
- Hot Tub
- Parking
- Pool
- Skiing
CA $4,102/Night
7 Nights - CA $28,717
House
7 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
CA $3,964/Night
7 Nights - CA $27,747
House
10.0(3 Reviews)
6 Bedrooms
16 Guests
- Hot Tub
- Parking
- Pool
- Skiing
CA $3,959/Night
7 Nights - CA $27,712
Top-Rated Villas with a Pool in Windsor County
Over 573+ Top-Rated Private Villas with a Pool in or Near Windsor County
Cabin
10.0(106 Reviews)
11 Bedrooms
32 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $1,987/Night
7 Nights - CA $13,906
House
10.0(92 Reviews)
4 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $1,932/Night
7 Nights - CA $13,524
House
10.0(82 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $2,788/Night
7 Nights - CA $19,518
House
10.0(80 Reviews)
4 Bedrooms
11 Guests
- Hot Tub
- Parking
- Pool
- Skiing
CA $683/Night
7 Nights - CA $4,780
Condo
10.0(64 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $1,274/Night
7 Nights - CA $8,916
CA $595/Night
7 Nights - CA $4,165
Condo
10.0(48 Reviews)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Skiing
CA $555/Night
7 Nights - CA $3,884
Bed & Breakfast
10.0(47 Reviews)
1 Bedroom
- Breakfast
- Parking
- Pool
- Balcony/Terrace
CA $318/Night
7 Nights - CA $2,229
CA $835/Night
7 Nights - CA $5,846
Pet-Friendly Villas in Windsor County
Over 586+ Pet-Friendly Private Villas in or Near Windsor County
House
10.0(53 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
View- Kitchen
CA $836/Night
7 Nights - CA $5,851
House
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Internet
Pet Friendly
Sports/Activities
CA $714/Night
7 Nights - CA $4,997
House
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $688/Night
7 Nights - CA $4,816
Apartment
10.0(42 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $361/Night
7 Nights - CA $2,523
House
10.0(1 Review)
6 Bedrooms
15 Guests
- Hot Tub
- Parking
- Spa
- View
CA $1,255/Night
7 Nights - CA $8,787
Ski Chalet
10.0(31 Reviews)
1 Bedroom
15 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $2,282/Night
7 Nights - CA $15,976
Cabin
10.0(27 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $614/Night
7 Nights - CA $4,299
Apartment
10.0(17 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $386/Night
7 Nights - CA $2,701
House
10.0(14 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $338/Night
7 Nights - CA $2,370
Large Private Villas in Windsor County
Over 572+ Large Villas in or Near Windsor County for Groups and Families
House
10.0(1 Review)
1 Bedroom
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $1,612/Night
7 Nights - CA $11,283
House
10.0(2 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Skiing
CA $704/Night
7 Nights - CA $4,931
Condo
10.0(1 Review)
2 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Spa
CA $746/Night
7 Nights - CA $5,224
House
10.0(1 Review)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Internet
Wellness Facilities
CA $1,228/Night
7 Nights - CA $8,597
Villa
9.6(15 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $340/Night
7 Nights - CA $2,377
Villa
9.0(2 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $284/Night
7 Nights - CA $1,988
CA $1,447/Night
7 Nights - CA $10,127
New
Villa
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $430/Night
7 Nights - CA $3,009
House
10.0(162 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $1,035/Night
7 Nights - CA $7,245
Wheelchair Accessible Holiday Homes in Windsor County
Over 48+ Wheelchair Accessible Villas and Holiday Homes in or Near Windsor County
Condo
10.0(38 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
CA $980/Night
7 Nights - CA $6,860
CA $414/Night
7 Nights - CA $2,898
CA $382/Night
7 Nights - CA $2,677
Condo
10.0(34 Reviews)
1 Bedroom
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
CA $541/Night
7 Nights - CA $3,789
Resort
8.9(211 Reviews)
47 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $288/Night
7 Nights - CA $2,015
Condo
10.0(13 Reviews)
1 Bedroom
6 Guests
- Hot Tub
- Parking
- Pool
- Spa
CA $391/Night
7 Nights - CA $2,736
New
Condo
10.0(4 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Skiing
CA $220/Night
7 Nights - CA $1,537
CA $463/Night
7 Nights - CA $3,241
Condo
10.0(1 Review)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Skiing
CA $1,674/Night
7 Nights - CA $11,719
Windsor County Villas, Airbnb and Holiday Homes Under $200
Over 226+ Windsor County Private Villas, Airbnb and Holiday Homes Under $200
Condo
10.0(16 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $240/Night
7 Nights - CA $1,681
CA $252/Night
7 Nights - CA $1,761
Condo
6.8(3 Reviews)
1 Bedroom
- Hot Tub
- Parking
- Pool
- Kitchen
CA $225/Night
7 Nights - CA $1,578
Apartment
10.0(7 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Internet
- Pet Friendly
TV
CA $251/Night
7 Nights - CA $1,757
House
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Security/Safety
CA $209/Night
7 Nights - CA $1,465
Condo
10.0(6 Reviews)
1 Bedroom
4 Guests
- Kitchen
- Internet
- Child Friendly
Laundry
CA $276/Night
7 Nights - CA $1,934
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $269/Night
7 Nights - CA $1,880
Bed & Breakfast
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $244/Night
7 Nights - CA $1,708
House
10.0(1 Review)
1 Bedroom
2 Guests
- Breakfast
- Balcony/Terrace
- Air Conditioner
- Internet
CA $224/Night
7 Nights - CA $1,570
Instantly Bookable Villa Rentals in Windsor County
Over 1367+ Instantly Bookable Private Villas in or Near Windsor County
Cabin
10.0(54 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $569/Night
7 Nights - CA $3,983
CA $524/Night
7 Nights - CA $3,669
House
9.8(17 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
CA $584/Night
7 Nights - CA $4,084
Condo
10.0(41 Reviews)
2 Bedrooms
8 Guests
- Parking
- Skiing
- Balcony/Terrace
- Kitchen
CA $637/Night
7 Nights - CA $4,458
Condo
10.0(36 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $695/Night
7 Nights - CA $4,862
House
10.0(33 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Spa
Ocean View
CA $541/Night
7 Nights - CA $3,783
House
10.0(28 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
CA $517/Night
7 Nights - CA $3,618
Cabin
10.0(27 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $498/Night
7 Nights - CA $3,484
Condo
10.0(21 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Skiing
CA $559/Night
7 Nights - CA $3,913
Book a Last Minute Place to Stay in Windsor County
About Windsor County Vacation Rentals
There are more than 2384 incredible getaway rentals that are available in Windsor County. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Windsor County.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Windsor County, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Windsor County. Places to stay near Windsor County are 1150.4 ft² on average, with prices averaging CA $811 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Windsor County. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Windsor County, VT
There are 134 hotels in Windsor County 20 resorts, and 1564 rentals
- Prices for a holiday home in Windsor County start at CA $128
- Top rated vacation home in Windsor County is Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Most popular short term in Windsor County is Align Inn Vermont
- Cheapest place to stay in Windsor County is Super 8 by Wyndham White River Junction
- Most expensive holiday rental in Windsor County is Reading Farms Estate
Recently Booked Hotels, Resorts, or Rentals in Windsor County
Frequently Asked Questions About Windsor County?
What are the top hotels or resorts in Windsor County?
We provide an array of great vacation destinations in Windsor County. If you are looking to stay in or around the Windsor County area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windsor County:
- Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Luxurious, Secluded, Ski Chalet, w/Country Decor & Hot Tub Near Okemo
- GORGEOUS LAKEFRONT - Autumn Splendor - Private Setting - 5 Mins to Okemo!
- Perfect Design & Location for the VT Experience. "Hope Upon, Up Above"
- Quiet Vermont Winter Getaway
- Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
- Sleeps 32 - 11BR - 1/2 Mile to Okemo - Hot Tub - Walk to Downtown Ludlow
- Scenic South Woodstock, Vermont home
- Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
- Spacious home on picturesque grounds with stunning views. Quechee - Woodstock
How many vacation rentals have private pools in Windsor County?
We have 68 luxury villas and vacation rentals featuriung a private pool in and near Windsor County. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel or resort in Windsor County is best for families?
Searching for a family-friendly getaway in Windsor County? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Windsor County?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 2384 in the Windsor County area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Windsor County.
