Estia Villas - Vacation Rentals in Windham County
Villa
10.0
(
8 Reviews
)
7 Bedrooms
4 Bathrooms
18 Guests
6800 ft²
-
Private Pool -
Hot Tub -
Parking -
Pool
US $1,567
/Night
7 Nights - $10,966
House
10.0
(
4 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
2798.62 ft²
-
EV Charge Station -
Parking
-
Pool
-
View
US $677
/Night
7 Nights - $4,739
Villa
10.0
(
1 Review
)
4 Bedrooms
4 Bathrooms
11 Guests
-
Hot Tub
-
Internet -
Pet Friendly -
Child Friendly
US $783
/Night
7 Nights - $5,482
Villa
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
10 Guests
-
Hot Tub
-
Kitchen -
Air Conditioner -
Internet
US $633
/Night
7 Nights - $4,431
Villa
10.0
(
1 Review
)
1 Bedroom
3 Bathrooms
9 Guests
-
Hot Tub
-
Parking
-
Pool
-
Kitchen
US $612
/Night
7 Nights - $4,286
Villa
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
9 Guests
-
Hot Tub
-
Air Conditioner
-
Internet
-
Child Friendly
US $596
/Night
7 Nights - $4,173
Villa
10.0
(
1 Review
)
4 Bedrooms
4 Bathrooms
8 Guests
-
Hot Tub
-
Pool
-
Kitchen
-
Internet
US $567
/Night
7 Nights - $3,966
Villa
9.8
(
10 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
-
Hot Tub
-
Parking
-
Spa -
Kitchen
US $466
/Night
7 Nights - $3,260
See More Windham County Vacation Rentals
Luxury Places to Stay in Windham County
Over 1960+
Luxury Places to Stay in or Near Windham County
US $3,540
/Night
7 Nights - $24,778
Bed & Breakfast
9 Bedrooms
9 Bathrooms
16 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $3,517
/Night
7 Nights - $24,616
Bed & Breakfast
9 Bedrooms
9 Bathrooms
27 Guests
-
Breakfast -
Parking
-
Balcony/Terrace -
Kitchen
US $3,354
/Night
7 Nights - $23,481
House
10.0
(
62 Reviews
)
11 Bedrooms
7 Bathrooms
30 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $3,129
/Night
7 Nights - $21,905
House
10.0
(
87 Reviews
)
10 Bedrooms
7 Bathrooms
27 Guests
7000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $3,061
/Night
7 Nights - $21,424
Villa
12 Bedrooms
13 Bathrooms
32 Guests
7997.59 ft²
-
Private Pool
-
Parking
-
Pool
-
Spa
US $3,043
/Night
7 Nights - $21,300
House
10.0
(
4 Reviews
)
7 Bedrooms
5 Bathrooms
16 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $3,012
/Night
7 Nights - $21,085
House
10.0
(
139 Reviews
)
10 Bedrooms
6 Bathrooms
24 Guests
6000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $2,991
/Night
7 Nights - $20,937
Find More Windham County Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Windham County
Over 520+
Top-Rated Vacation Rentals with a Pool in or Near Windham County
Apartment
10.0
(
181 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Pool
-
Skiing -
Balcony/Terrace
US $199
/Night
7 Nights - $1,392
Condo
10.0
(
154 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $426
/Night
7 Nights - $2,982
Condo
10.0
(
73 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $180
/Night
7 Nights - $1,259
House
10.0
(
66 Reviews
)
5 Bedrooms
3 Bathrooms
18 Guests
4000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $871
/Night
7 Nights - $6,100
Condo
10.0
(
54 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $216
/Night
7 Nights - $1,515
House
10.0
(
44 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2040 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $616
/Night
7 Nights - $4,315
House
10.0
(
44 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1800 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $413
/Night
7 Nights - $2,891
House
10.0
(
37 Reviews
)
4 Bedrooms
2 Bathrooms
11 Guests
2000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $652
/Night
7 Nights - $4,564
Pet-Friendly Vacation Rentals in Windham County
Over 624+
Pet-Friendly Vacation Rentals in or Near Windham County
Cabin
10.0
(
87 Reviews
)
3 Bedrooms
3 Bathrooms
7 Guests
1800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $475
/Night
7 Nights - $3,326
Bed & Breakfast
10.0
(
11 Reviews
)
10 Bedrooms
12 Bathrooms
20 Guests
2079.59 ft²
-
Private Pool
-
Private Beach -
Oceanfront -
Breakfast
US $626
/Night
7 Nights - $4,379
Cottage
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $736
/Night
7 Nights - $5,149
House
10.0
(
74 Reviews
)
6 Bedrooms
5 Bathrooms
14 Guests
4000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,223
/Night
7 Nights - $8,563
Cabin
9.6
(
169 Reviews
)
2 Bedrooms
1 Bathroom
10 Guests
-
Hot Tub
-
Parking
-
Ocean View -
Balcony/Terrace
US $368
/Night
7 Nights - $2,579
House
10.0
(
96 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $330
/Night
7 Nights - $2,309
Cabin
10.0
(
64 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $201
/Night
7 Nights - $1,407
Cabin
10.0
(
56 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $274
/Night
7 Nights - $1,921
See More Pet-Friendly Vacation Rentals in Windham County on PetFriendly.io
Large Vacation Homes & Villas in Windham County
Over 642+
Large Vacation Homes & Villas in or Near Windham County
House
10.0
(
118 Reviews
)
4 Bedrooms
3 Bathrooms
11 Guests
3000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $419
/Night
7 Nights - $2,931
Bed & Breakfast
10.0
(
10 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
409.03 ft²
-
Parking
-
Skiing
-
Balcony/Terrace
-
Air Conditioner
US $198
/Night
7 Nights - $1,386
House
9.6
(
27 Reviews
)
9 Bedrooms
5 Bathrooms
30 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,494
/Night
7 Nights - $10,457
Condo
9.4
(
11 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
2900 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $742
/Night
7 Nights - $5,197
House
10.0
(
10 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
4218 ft²
-
Parking
-
Pool
-
Skiing
-
Kitchen
US $1,371
/Night
7 Nights - $9,599
House
10.0
(
61 Reviews
)
6 Bedrooms
3 Bathrooms
12 Guests
2000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,003
/Night
7 Nights - $7,024
House
10.0
(
61 Reviews
)
4 Bedrooms
1 Bathroom
16 Guests
1671 ft²
-
Parking
-
Skiing
-
Ocean View
-
Balcony/Terrace
US $315
/Night
7 Nights - $2,207
House
10.0
(
58 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
2800 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,129
/Night
7 Nights - $7,906
See More Family Vacation Rentals in Windham County on FVR
Wheelchair Accessible Vacation Homes in Windham County
Over 49+
Wheelchair Accessible Vacation Homes in or Near Windham County
Condo
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
950 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $333
/Night
7 Nights - $2,330
Bed & Breakfast
9.1
(
204 Reviews
)
26 Bedrooms
9 Bathrooms
33 Guests
333.68 ft²
-
Hot Tub
-
EV Charge Station
-
Parking
-
Pool
US $167
/Night
7 Nights - $1,166
US $201
/Night
7 Nights - $1,407
Apartment
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $215
/Night
7 Nights - $1,507
Cabin
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $229
/Night
7 Nights - $1,606
Ski Chalet
10.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
8 Guests
2000 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $1,154
/Night
7 Nights - $8,077
Condo
3 Bedrooms
3 Bathrooms
12 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $665
/Night
7 Nights - $4,656
US $573
/Night
7 Nights - $4,010
Windham County Vacation Rentals and Airbnb Places to Stay Under $200
Over 191+
Windham County Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
16 Reviews
)
2 Bedrooms
1 Bathroom
2 Guests
280 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $162
/Night
7 Nights - $1,133
Apartment
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1679.17 ft²
-
Parking
-
Internet
-
Child Friendly
-
Security/Safety
US $199
/Night
7 Nights - $1,391
Bed & Breakfast
9.8
(
268 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
US $183
/Night
7 Nights - $1,282
House
10.0
(
7 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1291 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $145
/Night
7 Nights - $1,012
Apartment
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $190
/Night
7 Nights - $1,329
Apartment
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Child Friendly
-
Bedding/Linens
US $194
/Night
7 Nights - $1,357
Cabin
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
400 ft²
-
Parking
-
Spa
-
Balcony/Terrace
-
Kitchen
US $147
/Night
7 Nights - $1,028
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $141
/Night
7 Nights - $984
See More Windham County Vacation Rental Deals
Instantly Bookable Vacation Homes in Windham County
Over 1083+
Instantly Bookable Vacation Homes in or Near Windham County
Condo
10.0
(
66 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1755 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $639
/Night
7 Nights - $4,473
Condo
9.8
(
97 Reviews
)
1 Bedroom
1 Bathroom
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $374
/Night
7 Nights - $2,619
House
10.0
(
16 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Parking
-
Pool
-
Skiing
-
Balcony/Terrace
US $390
/Night
7 Nights - $2,733
Cabin
10.0
(
72 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1600 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $829
/Night
7 Nights - $5,802
House
9.8
(
26 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Parking
-
Pool
-
Skiing
-
Balcony/Terrace
US $613
/Night
7 Nights - $4,291
House
9.4
(
62 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $297
/Night
7 Nights - $2,079
House
10.0
(
21 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
2000 ft²
-
Parking
-
Pool
-
Spa
-
Balcony/Terrace
US $535
/Night
7 Nights - $3,748
House
9.4
(
24 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
2000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $471
/Night
7 Nights - $3,297
About Windham County Vacation Rentals
With more than 29 Windham 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 Windham County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Windham 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 Windham County. Places to stay near Windham County are 2620.66 ft² on average, with prices averaging US $1,092 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Windham 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.
Use these Quick Filters to Find a Vacation Rental in Windham 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 Windham County.
Weather in Windham County
View the weather forecast for Windham County before booking your Windham 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 Windham County, VT
Estiavillas offers a large selection of top attractions around Windham County. Research things to do on your vacation before you visit Windham County.
Mount Snow
Stratton Mountain Resort
Magic Mountain Ski Resort
Bellows Falls Opera House
American Express Ski Lift
Stratton Mountain Summit Gondola Ski Lift
Vermont Country Store
Brattleboro Bowl
Landmark College
The Putney School
Viking Nordic Center
Brattleboro Outlet Center
Brattleboro Farmers' Market
Ball Mountain Dam
The Stone Church
Brattleboro Country Club
Villager Ski Lift
Plummer's Sugar House
Jamaica State Park
South American Ski Lift
Solstice Ski Lift
Brattleboro Common
Mount Snow Golf Course
Ball Mountain State Park
Lake Raponda
Jacksonville Pond
Snow Bowl Ski Lift
Jud Hartmann Gallery
Creamery Covered Bridge
Marlboro College
Other Places to Stay Near Windham County, VT
West Dover
490 Properties
Mount Snow Valley
490 Properties
Wilmington
201 Properties
West Halifax
116 Properties
Jamaica
70 Properties
Putney
70 Properties
Wardsboro
45 Properties
Brattleboro
43 Properties
Whitingham
42 Properties
Stratton
41 Properties
South Londonderry
24 Properties
Townshend
24 Properties
Complexes around Windham County, VT
Inn Rm West Dover
18 Properties
Holiday Inn Express Hotel Brattleboro Ihg
3 Properties
The Putney Inn
3 Properties
Timber Creek
3 Properties
Farmhouse Farm Road Estate Mt Snow
2 Properties
Mountain Inn
2 Properties
Colonial Motel
1 Properties
Crafts Inn Wilmington
1 Properties
Mountain Retreat Wilmington
1 Properties
Mt Snow Ski Trail Shuttle Green Mountain
1 Properties
Windham County Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Windham County?
There are a lot of options in Windham County. If you plan on staying in the Windham 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 Windham County:
- The Myrtle Villa Hot Tub Pool Near Mount Snow
- The Villa - Industrial Farmhouse with Hot Tub
- Trailedge Townhome-Ski on/off, Walk to lodge
- New Townhome, Minutes from Mtn & lakes. Hottub
- New Construction- min from Mt, Hot tub, Shuttle
- Greenspring townhome- Free shuttle and clubhouse
- New Townhome- Minutes from Mountain, Hot tub, game room
- Greenspring Townhome at Mount Snow with free shuttle, Amenities
- New! Family Townhome with Hot Tub, Shuttle service
- New! Mt Snow Condo. Walk to lifts, pool, Hot tub
How many vacation rentals have private pools in Windham County?
There are 63 vacation rentals with private pools near Windham County. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Windham County are best for families?
If you are looking for a family-friendly vacation home in Windham 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 Windham County:
How many vacation rentals are available in Windham County?
Currently, the total number of properties listed in 2026 is over 29 in the Windham County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windham County.
