Estia Villas - Vacation Rentals in Windham County
US $1,725
/Night
7 Nights - $12,075
See More Windham County Vacation Rentals
Luxury Places to Stay in Windham County
Over 100+
Luxury Places to Stay in or Near Windham County
House
10.0
(
15 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
3600 ft²
-
Private Pool -
Parking -
Pool -
Ocean View
US $1,150
/Night
7 Nights - $8,047
House
10.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
10 Guests
-
Child Friendly -
Security/Safety
US $1,009
/Night
7 Nights - $7,063
Cottage
1 Bedroom
1 Bathroom
-
Parking
-
Ocean View
-
Balcony/Terrace -
View
US $904
/Night
7 Nights - $6,329
House
9.8
(
87 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen -
Air Conditioner
US $770
/Night
7 Nights - $5,390
House
10.0
(
27 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $738
/Night
7 Nights - $5,168
New
House
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $698
/Night
7 Nights - $4,886
House
10.0
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1300 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $695
/Night
7 Nights - $4,863
House
10.0
(
8 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
2363 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $676
/Night
7 Nights - $4,729
Find More Windham County Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Windham County
Over 11+
Top-Rated Vacation Rentals with a Pool in or Near Windham County
House
9.8
(
20 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2800 ft²
-
Breakfast -
Parking
-
Pool
-
Ocean View
US $539
/Night
7 Nights - $3,770
House
9.8
(
9 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
1000 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $187
/Night
7 Nights - $1,308
Hotel
7.6
(
1006 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Kitchen
US $102
/Night
7 Nights - $717
Hotel
7.0
(
382 Reviews
)
290.63 ft²
-
Private Pool
-
Parking
-
Pool
-
Kitchen
US $70
/Night
7 Nights - $487
US $425
/Night
7 Nights - $2,978
Cabin
10.0
(
1 Review
)
3 Bedrooms
1 Bathroom
8 Guests
-
Oceanfront -
Parking
-
Pool
-
Ocean View
US $352
/Night
7 Nights - $2,461
Cabin
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
2 Guests
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $209
/Night
7 Nights - $1,463
Other
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
5 Guests
1250 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $202
/Night
7 Nights - $1,417
Pet-Friendly Vacation Rentals in Windham County
Over 37+
Pet-Friendly Vacation Rentals in or Near Windham County
Apartment
10.0
(
19 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
340 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $227
/Night
7 Nights - $1,587
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
753.47 ft²
-
Parking
-
Pet Friendly -
Child Friendly
-
Sports/Activities
US $175
/Night
7 Nights - $1,224
Cottage
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $426
/Night
7 Nights - $2,985
House
9.8
(
34 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $234
/Night
7 Nights - $1,636
House
9.8
(
16 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Hot Tub -
Parking
-
Balcony/Terrace
-
Kitchen
US $430
/Night
7 Nights - $3,009
Cottage
9.6
(
40 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
1502 ft²
-
Parking
-
Skiing -
Balcony/Terrace
-
Kitchen
US $426
/Night
7 Nights - $2,982
House
9.6
(
22 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2150 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $452
/Night
7 Nights - $3,166
House
9.6
(
5 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
-
Air Conditioner
-
Internet -
Pet Friendly
-
Child Friendly
US $264
/Night
7 Nights - $1,851
See More Pet-Friendly Vacation Rentals in Windham County on PetFriendly.io
Large Vacation Homes & Villas in Windham County
Over 12+
Large Vacation Homes & Villas in or Near Windham County
House
7.4
(
3 Reviews
)
1 Bedroom
2 Bathrooms
10 Guests
2100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $434
/Night
7 Nights - $3,038
House
7 Bedrooms
7 Bathrooms
14 Guests
5500.36 ft²
-
Parking
-
Internet
-
Child Friendly
-
Wheelchair Accessible
US $584
/Night
7 Nights - $4,088
New
House
3 Bedrooms
2 Bathrooms
14 Guests
4000 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $494
/Night
7 Nights - $3,458
House
10.0
(
3 Reviews
)
6 Bedrooms
6 Bathrooms
12 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $780
/Night
7 Nights - $5,458
House
6.8
(
11 Reviews
)
7 Bedrooms
7 Bathrooms
14 Guests
5294 ft²
-
Hot Tub
-
Parking
-
Skiing
-
Balcony/Terrace
US $666
/Night
7 Nights - $4,662
House
3.3
(
3 Reviews
)
7 Bedrooms
7 Bathrooms
14 Guests
5500 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Bedding/Linens
US $683
/Night
7 Nights - $4,781
House
1 Bedroom
4 Bathrooms
16 Guests
4198 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $908
/Night
7 Nights - $6,356
House
6 Bedrooms
6 Bathrooms
14 Guests
-
Hot Tub
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $499
/Night
7 Nights - $3,493
See More Family Vacation Rentals in Windham County on FVR
Wheelchair Accessible Vacation Homes in Windham County
Over 6+
Wheelchair Accessible Vacation Homes in or Near Windham County
House
1.0
(
1 Review
)
4 Bedrooms
4 Bathrooms
8 Guests
2949.31 ft²
-
Parking
-
Internet
-
Child Friendly
-
Wheelchair Accessible
US $271
/Night
7 Nights - $1,897
US $99
/Night
7 Nights - $695
US $110
/Night
7 Nights - $770
Hotel
7.0
(
109 Reviews
)
355.21 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Air Conditioner
US $76
/Night
7 Nights - $530
US $90
/Night
7 Nights - $630
Windham County Vacation Rentals and Airbnb Places to Stay Under $200
Over 24+
Windham County Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
33 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $193
/Night
7 Nights - $1,348
Apartment
9.5
(
4 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
344.45 ft²
-
Parking
-
Internet
-
Pet Friendly
-
Child Friendly
US $183
/Night
7 Nights - $1,279
Bed & Breakfast
10.0
(
39 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Kitchen
-
Air Conditioner
US $199
/Night
7 Nights - $1,396
Apartment
10.0
(
19 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $173
/Night
7 Nights - $1,211
Cabin
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $149
/Night
7 Nights - $1,041
House
9.4
(
39 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $194
/Night
7 Nights - $1,356
Cottage
10.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $168
/Night
7 Nights - $1,179
House
9.8
(
14 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1300 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $199
/Night
7 Nights - $1,390
See More Windham County Vacation Rental Deals
Instantly Bookable Vacation Homes in Windham County
Over 18+
Instantly Bookable Vacation Homes in or Near Windham County
House
10.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
825 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $427
/Night
7 Nights - $2,990
Cottage
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
698 ft²
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $314
/Night
7 Nights - $2,196
Apartment
8.8
(
5 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $255
/Night
7 Nights - $1,787
House
8.0
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $427
/Night
7 Nights - $2,989
New
House
1 Bedroom
1 Bathroom
4 Guests
750 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $248
/Night
7 Nights - $1,738
New
House
3 Bedrooms
4 Bathrooms
3 Guests
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $209
/Night
7 Nights - $1,465
House
9.8
(
60 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2350 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $379
/Night
7 Nights - $2,650
House
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,160
/Night
7 Nights - $8,117
About Windham County Vacation Rentals
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 with prices averaging US $1,725 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.
Top Rental Accommodation Types in Windham County
| Type | Count |
|---|---|
| Villas | 1 |
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, CT
Estiavillas offers a large selection of top attractions around Windham County. Research things to do on your vacation before you visit Windham County.
Brooklyn Golf Course
Bradley Playhouse
Eastern Connecticut State University
Canterbury Green
Chaplin Museum
Woodstock Golf Course
Killingly Shopping Center
Skydive Danielson
Thompson International Speedway
Brooklyn Country Club
Taylor Brooke Winery
Little River Plaza Shopping Center
Old Furnace State Park
New England Center for Contemporary Art at Brooklyn
Sharpe Hill Vineyard
Brooklyn Recreation Park
Martha's Herbary
Davis Park
Squaw Rock State Park
Rotary Park
Roseland Cottage
Brooklyn Common Shopping Center
Tinkerville Brook Reserve
Harrisville Golf Course
Nathaniel Lyon Memorial Park
Nickerson Park
Moosup Pond Beach
Roseland Park Golf Course
Killingly Pond State Park
Quaddick Reservoir
Other Places to Stay Near Windham County, CT
Woodstock
167 Properties
Ashford
154 Properties
Canterbury
152 Properties
Plainfield
119 Properties
Hampton
100 Properties
Hampton Hill Historic District
99 Properties
Putnam
49 Properties
Thompson
37 Properties
Dayville
37 Properties
Pomfret
31 Properties
Killingly
29 Properties
Danielson
25 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:
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 1 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.
