Estia Villas - Vacation Rentals in Windsor County
Villa
9.6
(
18 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
-
Parking -
Balcony/Terrace -
Kitchen -
Air Conditioner
US $265
/Night
7 Nights - $1,852
Villa
9.6
(
15 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $229
/Night
7 Nights - $1,601
Villa
3 Bedrooms
3 Bathrooms
7 Guests
-
Air Conditioner
-
Internet -
Child Friendly -
Barbecue/Outdoor Cooking
US $525
/Night
7 Nights - $3,675
Villa
9.6
(
8 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
-
Hot Tub -
Pool -
Skiing -
Kitchen
US $1,707
/Night
7 Nights - $11,947
See More Windsor County Vacation Rentals
Luxury Places to Stay in Windsor County
Over 2254+
Luxury Places to Stay in or Near Windsor County
House
16 Bedrooms
19 Bathrooms
39 Guests
-
Internet
-
Child Friendly
-
Security/Safety
US $4,854
/Night
7 Nights - $33,979
House
10.0
(
3 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $3,725
/Night
7 Nights - $26,073
Condo
10.0
(
40 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
1800 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $3,030
/Night
7 Nights - $21,211
New
House
4 Bedrooms
3 Bathrooms
10 Guests
2045.14 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $2,949
/Night
7 Nights - $20,640
Condo
10.0
(
3 Reviews
)
4 Bedrooms
3 Bathrooms
14 Guests
2000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $2,605
/Night
7 Nights - $18,233
Condo
10.0
(
4 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1000 ft²
-
Private Pool -
Parking
-
Pool
-
Skiing
US $2,568
/Night
7 Nights - $17,975
Condo
10.0
(
36 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1350 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $2,556
/Night
7 Nights - $17,889
House
4 Bedrooms
2 Bathrooms
7 Guests
-
Pet Friendly -
Child Friendly
-
Security/Safety
US $2,518
/Night
7 Nights - $17,624
Find More Windsor County Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Windsor County
Over 520+
Top-Rated Vacation Rentals with a Pool in or Near Windsor County
Cabin
10.0
(
105 Reviews
)
11 Bedrooms
7 Bathrooms
32 Guests
4000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $1,410
/Night
7 Nights - $9,870
House
10.0
(
91 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
3800 ft²
-
Parking
-
Pool
-
Ocean View -
Balcony/Terrace
US $1,085
/Night
7 Nights - $7,596
House
10.0
(
80 Reviews
)
4 Bedrooms
2 Bathrooms
11 Guests
2000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $492
/Night
7 Nights - $3,441
Ski Chalet
10.0
(
75 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1400 ft²
-
Parking
-
Pool
-
Spa -
Ocean View
US $430
/Night
7 Nights - $3,012
Condo
10.0
(
64 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1240 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $840
/Night
7 Nights - $5,877
Bed & Breakfast
10.0
(
51 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast -
Parking
-
Pool
-
Spa
US $422
/Night
7 Nights - $2,956
Condo
10.0
(
46 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1248 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $390
/Night
7 Nights - $2,733
Condo
10.0
(
45 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $593
/Night
7 Nights - $4,149
Pet-Friendly Vacation Rentals in Windsor County
Over 570+
Pet-Friendly Vacation Rentals in or Near Windsor County
House
10.0
(
67 Reviews
)
5 Bedrooms
3 Bathrooms
22 Guests
5000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $946
/Night
7 Nights - $6,625
House
8.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
499.98 ft²
-
Parking
-
Pet Friendly
US $157
/Night
7 Nights - $1,099
US $95
/Night
7 Nights - $662
Cabin
9.8
(
152 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1400 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $281
/Night
7 Nights - $1,970
House
9.8
(
75 Reviews
)
4 Bedrooms
2 Bathrooms
12 Guests
2150 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $621
/Night
7 Nights - $4,347
House
9.6
(
142 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1750 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $251
/Night
7 Nights - $1,759
House
9.8
(
51 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
3000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $432
/Night
7 Nights - $3,026
House
9.6
(
34 Reviews
)
5 Bedrooms
2 Bathrooms
8 Guests
2000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $339
/Night
7 Nights - $2,373
See More Pet-Friendly Vacation Rentals in Windsor County on PetFriendly.io
Large Vacation Homes & Villas in Windsor County
Over 530+
Large Vacation Homes & Villas in or Near Windsor County
House
10.0
(
160 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
3302 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $729
/Night
7 Nights - $5,102
Apartment
9.5
(
2 Reviews
)
4 Bedrooms
2 Bathrooms
11 Guests
1603.82 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $164
/Night
7 Nights - $1,148
Cabin
9.8
(
103 Reviews
)
4 Bedrooms
4 Bathrooms
14 Guests
3000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $521
/Night
7 Nights - $3,650
House
9.8
(
126 Reviews
)
5 Bedrooms
2 Bathrooms
12 Guests
2000 ft²
-
Parking
-
Pool
-
Skiing
-
Balcony/Terrace
US $485
/Night
7 Nights - $3,394
Ski Chalet
9.4
(
27 Reviews
)
6 Bedrooms
2 Bathrooms
13 Guests
2300 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $620
/Night
7 Nights - $4,339
House
10.0
(
121 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
3000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $581
/Night
7 Nights - $4,065
New
Cabin
10.0
(
96 Reviews
)
4 Bedrooms
3 Bathrooms
14 Guests
3000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $772
/Night
7 Nights - $5,403
House
10.0
(
58 Reviews
)
5 Bedrooms
3 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $903
/Night
7 Nights - $6,324
See More Family Vacation Rentals in Windsor County on FVR
Wheelchair Accessible Vacation Homes in Windsor County
Over 50+
Wheelchair Accessible Vacation Homes in or Near Windsor County
Condo
10.0
(
38 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $695
/Night
7 Nights - $4,865
Bed & Breakfast
9.2
(
6 Reviews
)
9 Bedrooms
8 Bathrooms
21 Guests
176.26 ft²
-
Parking
-
Pool
-
Skiing
-
View
US $270
/Night
7 Nights - $1,892
US $261
/Night
7 Nights - $1,824
Condo
10.0
(
34 Reviews
)
1 Bedroom
2 Bathrooms
6 Guests
976 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $360
/Night
7 Nights - $2,519
Condo
10.0
(
12 Reviews
)
1 Bedroom
2 Bathrooms
6 Guests
976 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $280
/Night
7 Nights - $1,962
Condo
9.6
(
7 Reviews
)
1 Bedroom
1 Bathroom
6 Guests
1044 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $341
/Night
7 Nights - $2,386
Condo
5 Bedrooms
3 Bathrooms
12 Guests
2230 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $1,236
/Night
7 Nights - $8,655
Condo
4 Bedrooms
3 Bathrooms
12 Guests
1880 ft²
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $820
/Night
7 Nights - $5,737
Windsor County Vacation Rentals and Airbnb Places to Stay Under $200
Over 226+
Windsor County Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
55 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $123
/Night
7 Nights - $859
Apartment
10.0
(
9 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
150.69 ft²
-
Pool
-
Skiing
-
Air Conditioner
-
Internet
US $189
/Night
7 Nights - $1,320
Bed & Breakfast
9.6
(
301 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
US $197
/Night
7 Nights - $1,378
Condo
10.0
(
16 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
750 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $170
/Night
7 Nights - $1,193
Cabin
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
350 ft²
-
Parking
-
Spa
-
Balcony/Terrace
-
Kitchen
US $190
/Night
7 Nights - $1,328
Bed & Breakfast
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
344 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $184
/Night
7 Nights - $1,285
Cabin
9.8
(
25 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
500 ft²
-
Parking
-
Kitchen
-
Internet
-
Pet Friendly
US $161
/Night
7 Nights - $1,130
Apartment
9.8
(
17 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $158
/Night
7 Nights - $1,109
See More Windsor County Vacation Rental Deals
Instantly Bookable Vacation Homes in Windsor County
Over 1278+
Instantly Bookable Vacation Homes in or Near Windsor County
Cabin
9.8
(
116 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $235
/Night
7 Nights - $1,646
US $372
/Night
7 Nights - $2,604
Cottage
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $494
/Night
7 Nights - $3,458
House
9.8
(
87 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1450 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $510
/Night
7 Nights - $3,568
House
10.0
(
20 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
2525 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,113
/Night
7 Nights - $7,793
House
9.8
(
63 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $363
/Night
7 Nights - $2,543
Condo
10.0
(
20 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $489
/Night
7 Nights - $3,426
House
9.4
(
40 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1300 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $413
/Night
7 Nights - $2,890
About Windsor County Vacation Rentals
With more than 4 Windsor County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windsor County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Windsor County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windsor County. Places to stay near Windsor County with prices averaging US $681 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Windsor County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Windsor County
| Type | Count |
|---|---|
| Villas | 4 |
Use these Quick Filters to Find a Vacation Rental in Windsor County
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windsor County.
Weather in Windsor County
View the weather forecast for Windsor County before booking your Windsor County Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Windsor County, VT
Estiavillas offers a large selection of top attractions around Windsor County. Research things to do on your vacation before you visit Windsor County.
Okemo Mountain Resort
Quechee Gorge
Jackson Gore Ski Resort at Okemo
King Arthur Flour
Quechee Gorge Village
Little Pico Mountain
Weston Playhouse
Suicide Six Ski Area
Weston Priory
Mt Ascutney State Park
Upper Valley Aquatic Center
Sugarbush Farm
Simon Pearce Mill
Mount Ascutney
Woodstock Country Club
Billings Farm and Museum
Okemo Valley Golf Club
Silver Lake State Park
Vermont River Tubing
Woodstock Town Hall Theatre
Briggs Opera House
Montshire Museum of Science
Wilderness Trails
Buttermilk Falls
Long Trail Brewing Company
Calvin Coolidge Historic Site
Mount Tom Peak
Vermont Institiute of Natural Science
Calvin Coolidge Homestead
Harpoon Brewery
Other Places to Stay Near Windsor County, VT
Ludlow
599 Properties
Bridgewater Corners
93 Properties
Woodstock
76 Properties
West Bridgewater
64 Properties
Cavendish
59 Properties
Quechee
58 Properties
Plymouth
56 Properties
Chester
50 Properties
Chester Depot
50 Properties
Proctorsville
30 Properties
Weston
26 Properties
West Windsor
24 Properties
Complexes around Windsor County, VT
Cedarbrook
28 Properties
Winterplace Ludlow
22 Properties
Located
16 Properties
Okemo Mountain Lodge
11 Properties
Efficiency Sofa
8 Properties
Kettle Brook
8 Properties
Hotel
6 Properties
Ghia Farm Road
4 Properties
Br Of Ski Lift
3 Properties
Comfort Inn White River Junction
3 Properties
Hampton Inn White River Junction
3 Properties
Holiday Inn Club Vacations Mount Ascutney Resort Ihg Hotel
3 Properties
Holiday Inn Express Hotel White River Junction Ihg
3 Properties
Hotel Coolidge
3 Properties
Solitude Bball Court
3 Properties
Windsor County Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Windsor County?
There are a lot of options in Windsor County. If you plan on staying in the Windsor County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor County:
How many vacation rentals have private pools in Windsor County?
There are 69 vacation rentals with private pools near Windsor County. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Windsor County are best for families?
If you are looking for a family-friendly vacation home in Windsor County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor County:
How many vacation rentals are available in Windsor County?
Currently, the total number of properties listed in 2026 is over 4 in the Windsor County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windsor County.
