Windham Holiday Rentals
House
- Connecticut
- ·
- Mansfield Depot
- 1.51 mi to center
10.0Exceptional
(79 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
Parking
Ocean View
Balcony/Terrace
View
US $449/Night
7 Nights - US $3,140
House
- Mystic - New London
- ·
- Norwich
- 1.00 mi to center
10.0Exceptional
(4 Reviews)
5 Bedrooms
4 Baths
10 Guests
4133.34 ft²
- Parking
- Balcony/Terrace
- View
Internet
US $491/Night
7 Nights - US $3,439
House
- Willington
- ·
- Mansfield
- 0.71 mi to center
8.8Fabulous
(121 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
US $262/Night
7 Nights - US $1,835
Cottage
- Connecticut
- ·
- Mansfield Depot
- 1.63 mi to center
10.0Exceptional
(35 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $323/Night
7 Nights - US $2,264
House
- Willington
- ·
- Hampton Hill Historic District
- 0.41 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1506.95 ft²
- Parking
Spa
Skiing- View
US $257/Night
7 Nights - US $1,801
House
- Connecticut
- ·
- Andover
- 1.55 mi to center
10.0Exceptional
(28 Reviews)
2 Bedrooms
1 Bath
6 Guests
1800 ft²
Hot Tub- Parking
- Ocean View
- Balcony/Terrace
US $237/Night
7 Nights - US $1,661
Cottage
- Willington
- ·
- Coventry Lake
- 0.99 mi to center
10.0Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $468/Night
7 Nights - US $3,273
House
- Willington
- ·
- Coventry Lake
- 0.31 mi to center
10.0Exceptional
(22 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $256/Night
7 Nights - US $1,794
House
- Willington
- ·
- Hampton
- 1.50 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Air Conditioner
- Internet
Pet Friendly
Child Friendly
US $264/Night
7 Nights - US $1,851
Luxury Holiday Rentals in Windham
Over 152+ Luxury Holiday Rentals in or Near Windham
House
- Willington
- ·
- Coventry Lake
- 0.95 mi to center
10.0Exceptional
(9 Reviews)
5 Bedrooms
5 Baths
15 Guests
5746 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $2,043/Night
7 Nights - US $14,298
House
- Willington
- ·
- Coventry Lake
- 0.44 mi to center
10.0Exceptional
(40 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,991/Night
7 Nights - US $13,936
House
- Mystic - New London
- ·
- Norwich
- 1.19 mi to center
9.2Exceptional
(39 Reviews)
10 Bedrooms
4 Baths
14 Guests
5000 ft²
Private Pool- Hot Tub
- Parking
Pool
US $1,071/Night
7 Nights - US $7,499
House
- Mystic - New London
- ·
- Baltic
- 0.16 mi to center
10.0Exceptional
(24 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $903/Night
7 Nights - US $6,323
House
- Mystic - New London
- ·
- Norwich
- 1.18 mi to center
10.0Exceptional
(4 Reviews)
5 Bedrooms
1 Bath
11 Guests
3336 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $826/Night
7 Nights - US $5,781
House
- Mystic - New London
- ·
- Norwichtown
- 2.34 mi to center
8.8Fabulous
(6 Reviews)
9 Bedrooms
4 Baths
16 Guests
4000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $824/Night
7 Nights - US $5,765
House
- Mystic - New London
- ·
- Norwichtown
- 1.22 mi to center
9.6Exceptional
(19 Reviews)
4 Bedrooms
2 Baths
10 Guests
3800 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $808/Night
7 Nights - US $5,654
House
- Mystic - New London
- ·
- Norwichtown
- 0.79 mi to center
9.8Exceptional
(17 Reviews)
7 Bedrooms
3 Baths
14 Guests
5000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $779/Night
7 Nights - US $5,456
House
- Mystic - New London
- ·
- Bozrah
- 0.51 mi to center
10.0Exceptional
(5 Reviews)
5 Bedrooms
2 Baths
8 Guests
5000 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $671/Night
7 Nights - US $4,696
Top-Rated Holiday Rentals with a Pool in Windham
Over 18+ The Best Private Villas and Holiday Rentals in Windham with a Pool
House
- Connecticut
- ·
- Mansfield Depot
- 1.63 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399.31 ft²
- Parking
- Pool
- Internet
- Pet Friendly
US $371/Night
7 Nights - US $2,597
Apartment
- Mystic - New London
- ·
- Norwichtown
- 0.53 mi to center
9.8Exceptional
(30 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $286/Night
7 Nights - US $2,002
House
- Connecticut
- ·
- Canterbury
- 3.63 mi to center
9.8Exceptional
(9 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $184/Night
7 Nights - US $1,289
Cottage
- Mystic - New London
- ·
- Norwichtown
- 1.26 mi to center
9.6Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $350/Night
7 Nights - US $2,450
Hotel
- Mystic - New London
- ·
- Griswold
- 0.90 mi to center
8.8Fabulous
(1001 Reviews)
1 Bath
- Hot Tub
Breakfast- Parking
- Pool
US $114/Night
7 Nights - US $798
House
- Connecticut
- ·
- Columbia
- 1.90 mi to center
8.8Fabulous
(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
5000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $406/Night
7 Nights - US $2,844
Hotel
- Mystic - New London
- ·
- Griswold
- 0.90 mi to center
8.3Excellent
(400 Reviews)
1 Bath
247.57 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
US $101/Night
7 Nights - US $707
Hotel
- Willington
- ·
- Mansfield Center
- 2.01 mi to center
8.0Excellent
(1007 Reviews)
1 Bath
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $195/Night
7 Nights - US $1,368
Hotel
- Mystic - New London
- ·
- Yantic
- 0.52 mi to center
7.8Very Good
(1163 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $101/Night
7 Nights - US $710
Pet-Friendly Holiday Rentals in Windham
Over 50+ Pet-Friendly Holiday Rentals in or Near Windham
Cottage
- Willington
- ·
- Coventry Lake
- 0.71 mi to center
9.4Exceptional
(29 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $213/Night
7 Nights - US $1,488
House
- Connecticut
- ·
- Gilman
- 2.64 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
1862.16 ft²
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $321/Night
7 Nights - US $2,247
Cottage
- Willington
- ·
- Hampton Hill Historic District
- 0.41 mi to center
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $426/Night
7 Nights - US $2,981
Cabin
- Willington
- ·
- Coventry Lake
- 0.96 mi to center
8.8Fabulous
(48 Reviews)
2 Bedrooms
1 Bath
6 Guests
764 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $243/Night
7 Nights - US $1,699
Apartment
- Mystic - New London
- ·
- Norwich
- 1.04 mi to center
9.8Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
11 Guests
1001.04 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $528/Night
7 Nights - US $3,694
New
House
- Connecticut
- ·
- Gilman
- 2.56 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $237/Night
7 Nights - US $1,661
House
- Willington
- ·
- Storrs
- 0.68 mi to center
10.0Exceptional
(11 Reviews)
3 Bedrooms
1 Bath
6 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $309/Night
7 Nights - US $2,160
House
- Willington
- ·
- Coventry Lake
- 0.92 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $345/Night
7 Nights - US $2,415
Cabin
- Willington
- ·
- Coventry Lake
- 0.45 mi to center
9.8Exceptional
(40 Reviews)
3 Bedrooms
1 Bath
6 Guests
972 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $372/Night
7 Nights - US $2,601
Large Holiday Rentals and Private Villas in Windham
Over 28+ Large Holiday Rentals and Private Villas in or Near Windham
House
- Willington
- ·
- Coventry Lake
- 0.42 mi to center
9.6Exceptional
(35 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $483/Night
7 Nights - US $3,378
Villa
- Connecticut
- ·
- Versailles
- 2.78 mi to center
3 Bedrooms
2 Baths
6 Guests
1603.82 ft²
EV Charge Station- Parking
- Air Conditioner
- Internet
US $552/Night
7 Nights - US $3,863
Cabin
- Connecticut
- ·
- Amston
- 0.09 mi to center
9.0Exceptional
(24 Reviews)
4 Bedrooms
2 Baths
10 Guests
3000 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $428/Night
7 Nights - US $2,993
House
- Connecticut
- ·
- Columbia
- 1.63 mi to center
8.0Excellent
(10 Reviews)
5 Bedrooms
2 Baths
9 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $450/Night
7 Nights - US $3,152
Cottage
- Connecticut
- ·
- Lebanon
- 3.32 mi to center
9.2Exceptional
(35 Reviews)
2 Bedrooms
1 Bath
10 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $353/Night
7 Nights - US $2,472
House
- Mystic - New London
- ·
- Norwich
- 1.00 mi to center
9.2Exceptional
(59 Reviews)
5 Bedrooms
3 Baths
10 Guests
4132 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $641/Night
7 Nights - US $4,484
House
- Connecticut
- ·
- Gilman
- 2.64 mi to center
9.0Exceptional
(32 Reviews)
3 Bedrooms
2 Baths
100 Guests
1860 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $327/Night
7 Nights - US $2,286
House
- Mystic - New London
- ·
- Norwich
- 1.43 mi to center
9.0Exceptional
(15 Reviews)
7 Bedrooms
2 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $386/Night
7 Nights - US $2,701
House
- Mystic - New London
- ·
- Norwich
- 1.37 mi to center
8.8Fabulous
(6 Reviews)
5 Bedrooms
2 Baths
12 Guests
2100 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $381/Night
7 Nights - US $2,669
Wheelchair Accessible Holiday Homes in Windham
Over 6+ Wheelchair Accessible Holiday Homes in or Near Windham
Hotel
- Willington
- ·
- Storrs
- 0.19 mi to center
9.1Exceptional
(359 Reviews)
1 Bath
3805.81 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $308/Night
7 Nights - US $2,155
Hotel
- Willington
- ·
- Storrs
- 0.21 mi to center
9.6Exceptional
(1000 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $232/Night
7 Nights - US $1,625
Hotel
- Mystic - New London
- ·
- Norwichtown
- 1.40 mi to center
7.8Very Good
(275 Reviews)
4 Baths
252.95 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $144/Night
7 Nights - US $1,006
Hotel
- Mystic - New London
- ·
- Norwichtown
- 1.44 mi to center
9.0Exceptional
(1005 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $137/Night
7 Nights - US $958
Hotel
- Mystic - New London
- ·
- Yantic
- 0.52 mi to center
6.9Good
(649 Reviews)
4 Baths
378.53 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $159/Night
7 Nights - US $1,111
Hotel
- Mystic - New London
- ·
- Norwichtown
- 1.45 mi to center
4.0Average
(95 Reviews)
1 Bath
355.21 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $104/Night
7 Nights - US $725
Windham Private Villas and Holiday Homes Under $200
Over 30+ Windham Private Villas and Holiday Homes Under $200
House
- Willington
- ·
- Storrs
- 1.25 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
3 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $84/Night
7 Nights - US $590
House
- Mystic - New London
- ·
- Jewett City
- 2.06 mi to center
7.5Very Good
(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
188.37 ft²
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $95/Night
7 Nights - US $665
Hotel
- Willington
- ·
- Chaplin
- 2.62 mi to center
8.6Fabulous
(56 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $97/Night
7 Nights - US $681
New
Apartment
- Willington
- ·
- Coventry Lake
- 0.71 mi to center
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $142/Night
7 Nights - US $994
House
- Connecticut
- ·
- Canterbury
- 3.63 mi to center
7.0Very Good
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
1001.04 ft²
- Parking
- Balcony/Terrace
- Internet
- Child Friendly
US $194/Night
7 Nights - US $1,360
House
- Mystic - New London
- ·
- Baltic
- 0.69 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,316
Apartment
- Mystic - New London
- ·
- Norwich
- 0.83 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $114/Night
7 Nights - US $797
House
- Mystic - New London
- ·
- Norwich
- 1.71 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,390
Hotel
- Mystic - New London
- ·
- Jewett City
- 1.91 mi to center
1 Bath
- Child Friendly
- Laundry
Bedding/Linens
Wellness Facilities
US $154/Night
7 Nights - US $1,075
Instantly Bookable Holiday Homes in Windham
Over 54+ Instantly Bookable Holiday Homes in or Near Windham
Apartment
- Willington
- ·
- South Coventry
- 0.19 mi to center
9.8Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
700 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $286/Night
7 Nights - US $2,005
New
Apartment
- Connecticut
- ·
- Mansfield Depot
- 1.61 mi to center
9.8Exceptional
(17 Reviews)
1 Bedroom
2 Baths
4 Guests
900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $282/Night
7 Nights - US $1,973
Cottage
- Willington
- ·
- Coventry Lake
- 0.41 mi to center
10.0Exceptional
(20 Reviews)
3 Bedrooms
1 Bath
6 Guests
1200 ft²
- Parking
- View
- Kitchen
- Air Conditioner
US $482/Night
7 Nights - US $3,371
House
- Willington
- ·
- Willimantic
- 0.42 mi to center
9.8Exceptional
(16 Reviews)
4 Bedrooms
2 Baths
8 Guests
1500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $450/Night
7 Nights - US $3,149
Cottage
- Willington
- ·
- Hampton Hill Historic District
- 0.41 mi to center
9.6Exceptional
(40 Reviews)
3 Bedrooms
1 Bath
8 Guests
1502 ft²
- Parking
- Skiing
- Balcony/Terrace
- Kitchen
US $337/Night
7 Nights - US $2,358
Cabin
- Willington
- ·
- Coventry Lake
- 0.52 mi to center
9.2Exceptional
(45 Reviews)
3 Bedrooms
1 Bath
6 Guests
640 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $323/Night
7 Nights - US $2,260
Cottage
- Connecticut
- ·
- Amston
- 0.52 mi to center
8.8Fabulous
(10 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $389/Night
7 Nights - US $2,725
House
- Mystic - New London
- ·
- Lisbon
- 1.01 mi to center
10.0Exceptional
(15 Reviews)
1 Bedroom
1 Bath
4 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $236/Night
7 Nights - US $1,655
Apartment
- Mystic - New London
- ·
- Norwich
- 0.69 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $231/Night
7 Nights - US $1,620
Book a Last Minute Place to Stay in Windham
About Casai's Private Villas and Holiday Rentals in Windham
Discover more than 161 vacation rentals available in Windham. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windham.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windham, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windham. On average, places to stay near Windham offer 952.99 ft², with nightly prices averaging US $416.
With Casai, finding and comparing holiday rentals in Windham is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Windham
| Type | Count |
|---|---|
| Vacation Homes | 98 |
| Holiday Apartments | 21 |
| Cottages | 19 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Windham
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Windham.
Weather in Windham, CT
View the weather forecast for Windham before booking your Windham 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, CT
Casai offers a large selection of top attractions around Windham . Research things to do on your vacation before you visit Windham.
Frequently Asked Questions About Windham?
What are the top holiday rentals in Windham?
With numerous options available in Windham, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windham:
- The Bungalow at Eagleville Lake Under 3 miles to UCONN!
- Updated Lakefront House *outdoor tv and water toys- 10 min from UConn
- Lakefront Connecticut Retreat Near UConn
- Spacious modern home on private lake
- Hanover Vineyards
- Lake Getaway at Coventry Lake! close to Uconn
- The Lake House
- Lakefront Cottage w/Covered Porch & Dock!
- A Lot Like Paradise. Quiet. Peaceful. Cozy. Spacious.
- Barn Stay at Hanover Vineyards
How many holiday rentals have private pools in Windham?
Discover a selection of holiday rentals with private pools near Windham with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Harland Haven - 4BR Home w/Pooln
- Mansion by the lake, Airline Trail and Wineries! In ground heated Pool-Jacuzzi.
Which holiday homes in Windham are best for families?
If you're searching for a family-friendly holiday home in Windham, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windham:
- Beautiful 1-bedroom apartment in Andover 10 miles to Uconn w/AC, Washer/Dryer
- Lakefront Cottage w/Covered Porch & Dock!
- Cozy Rural Guest House: Close to Wedding Venues
How many Casai.com holiday rentals are available in Windham?
As of 2026, Casai boasts over 161 properties listed in the Windham area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windham.
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