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
(
3 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
2798.62 ft²
-
Hot Tub
-
EV Charge Station -
Parking
-
Pool
US $677
/Night
7 Nights - $4,739
Villa
10.0
(
1 Review
)
4 Bedrooms
4 Bathrooms
11 Guests
-
Hot Tub
-
Internet -
Pet Friendly -
Laundry
US $783
/Night
7 Nights - $5,482
Villa
10.0
(
1 Review
)
1 Bedroom
3 Bathrooms
9 Guests
-
Hot Tub
-
Parking
-
Pool
-
Kitchen
US $651
/Night
7 Nights - $4,559
Villa
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
10 Guests
-
Hot Tub
-
Kitchen
-
Air Conditioner -
Internet
US $634
/Night
7 Nights - $4,441
Villa
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
9 Guests
-
Hot Tub
-
Air Conditioner
-
Internet
-
Child Friendly
US $598
/Night
7 Nights - $4,187
Villa
10.0
(
1 Review
)
4 Bedrooms
4 Bathrooms
8 Guests
-
Hot Tub
-
Pool
-
Kitchen
-
Internet
US $583
/Night
7 Nights - $4,084
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 1964+
Luxury Places to Stay in or Near Windham County
Villa
13 Bedrooms
13 Bathrooms
32 Guests
7997.59 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $4,413
/Night
7 Nights - $30,891
House
4 Bedrooms
3 Bathrooms
8 Guests
-
Air Conditioner
-
Internet
-
Laundry
-
Bedding/Linens
US $3,996
/Night
7 Nights - $27,974
US $3,540
/Night
7 Nights - $24,778
Bed & Breakfast
9 Bedrooms
9 Bathrooms
16 Guests
-
Air Conditioner
-
Internet
-
Laundry
-
Bedding/Linens
US $3,517
/Night
7 Nights - $24,616
Bed & Breakfast
9 Bedrooms
9 Bathrooms
27 Guests
-
Breakfast -
Parking
-
Balcony/Terrace -
Kitchen
US $3,442
/Night
7 Nights - $24,094
House
10.0
(
90 Reviews
)
10 Bedrooms
7 Bathrooms
27 Guests
7000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $3,058
/Night
7 Nights - $21,408
House
10.0
(
142 Reviews
)
10 Bedrooms
6 Bathrooms
28 Guests
6000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $2,984
/Night
7 Nights - $20,890
House
10.0
(
63 Reviews
)
11 Bedrooms
8 Bathrooms
30 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $2,976
/Night
7 Nights - $20,835
Find More Windham County Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Windham County
Over 499+
Top-Rated Vacation Rentals with a Pool in or Near Windham County
Condo
10.0
(
154 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $426
/Night
7 Nights - $2,982
House
10.0
(
75 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
2400 ft²
-
Parking
-
Pool
-
Ocean View -
Balcony/Terrace
US $1,023
/Night
7 Nights - $7,164
Condo
10.0
(
73 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $179
/Night
7 Nights - $1,251
House
10.0
(
72 Reviews
)
5 Bedrooms
3 Bathrooms
18 Guests
4000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $872
/Night
7 Nights - $6,104
Condo
10.0
(
56 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Hot Tub
-
Parking
-
Pool
-
Skiing
US $189
/Night
7 Nights - $1,321
House
10.0
(
46 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2040 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $513
/Night
7 Nights - $3,591
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 631+
Pet-Friendly Vacation Rentals in or Near Windham County
Cabin
10.0
(
88 Reviews
)
3 Bedrooms
3 Bathrooms
7 Guests
1800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $477
/Night
7 Nights - $3,336
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 $1,226
/Night
7 Nights - $8,582
Cabin
9.6
(
170 Reviews
)
2 Bedrooms
1 Bathroom
10 Guests
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $366
/Night
7 Nights - $2,564
House
10.0
(
98 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $329
/Night
7 Nights - $2,301
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
(
58 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $278
/Night
7 Nights - $1,944
See More Pet-Friendly Vacation Rentals in Windham County on PetFriendly.io
Large Vacation Homes & Villas in Windham County
Over 644+
Large Vacation Homes & Villas in or Near Windham County
House
10.0
(
122 Reviews
)
4 Bedrooms
3 Bathrooms
11 Guests
3000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $420
/Night
7 Nights - $2,939
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
US $554
/Night
7 Nights - $3,881
House
9.8
(
39 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
1900 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Child Friendly
US $774
/Night
7 Nights - $5,418
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 $820
/Night
7 Nights - $5,743
House
10.0
(
61 Reviews
)
3 Bedrooms
1 Bathroom
16 Guests
1671 ft²
-
Parking
-
Skiing
-
Ocean View
-
Balcony/Terrace
US $320
/Night
7 Nights - $2,243
See More Family Vacation Rentals in Windham County on FVR
Wheelchair Accessible Vacation Homes in Windham County
Over 46+
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
9.2
(
194 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 $220
/Night
7 Nights - $1,538
Ski Chalet
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
8 Guests
2000 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $1,151
/Night
7 Nights - $8,056
Cabin
9.4
(
3 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $234
/Night
7 Nights - $1,637
Condo
3 Bedrooms
3 Bathrooms
12 Guests
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $677
/Night
7 Nights - $4,740
US $582
/Night
7 Nights - $4,072
Windham County Vacation Rentals and Airbnb Places to Stay Under $200
Over 193+
Windham County Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
17 Reviews
)
2 Bedrooms
1 Bathroom
2 Guests
280 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $164
/Night
7 Nights - $1,149
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
Apartment
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $190
/Night
7 Nights - $1,329
Cabin
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
400 ft²
-
Parking
-
Spa
-
Balcony/Terrace
-
Kitchen
US $134
/Night
7 Nights - $937
Condo
9.6
(
11 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Internet
-
Laundry
US $168
/Night
7 Nights - $1,179
Cabin
9.6
(
8 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $138
/Night
7 Nights - $969
Apartment
9.4
(
3 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $142
/Night
7 Nights - $996
See More Windham County Vacation Rental Deals
Instantly Bookable Vacation Homes in Windham County
Over 1089+
Instantly Bookable Vacation Homes in or Near Windham County
Condo
10.0
(
66 Reviews
)
3 Bedrooms
2 Bathrooms
9 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
House
9.8
(
67 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1750 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Child Friendly
US $580
/Night
7 Nights - $4,062
Cabin
10.0
(
72 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1600 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $844
/Night
7 Nights - $5,908
House
9.8
(
26 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Parking
-
Pool
-
Skiing
-
Balcony/Terrace
US $612
/Night
7 Nights - $4,283
House
9.4
(
63 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $277
/Night
7 Nights - $1,939
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
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 2741.28 ft² on average, with prices averaging US $1,150 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
501 Properties
Mount Snow Valley
501 Properties
Wilmington
203 Properties
South Londonderry
146 Properties
Putney
70 Properties
Jamaica
69 Properties
Brattleboro
46 Properties
Wardsboro
43 Properties
Stratton
37 Properties
Newfane
30 Properties
Townshend
26 Properties
Whitingham
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
- Greenspring townhome- Free shuttle and clubhouse
- New Construction- min from Mt, Hot tub, Shuttle
- 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 61 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.
