A town with a prominent church, a river, and autumn foliage.

Windham County Vacation Rentals

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Top Cities in Windham County

A grassy field with cows grazing, a clear sky, and distant hills.
Vacation RentalsVacation Rentals

Plainfield

Plainfield

Our top choices for Windham County vacation rentals

A red building with a colorful mural on the front, a covered porch, and a stone foundation.

1. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is CA $178
CA $266 total
includes taxes & fees
Sep 27 - Sep 28
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

2. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is CA $178
CA $274 total
includes taxes & fees
Sep 27 - Sep 28
The Tree House at Underhill Hollow
A two-story house with a front porch, stone steps, and a driveway.

3. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is CA $176
CA $314 total
includes taxes & fees
Sep 27 - Sep 28
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

4. Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (25 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is CA $232
CA $483 total
includes taxes & fees
Sep 28 - Sep 29
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A small, single-story cabin with a porch and a small deck, surrounded by trees and a lake.

5. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (40 reviews)
"We had a nice stay in this cabin by the lake. It was close to UCONN so the convenience of the location was wonderful. "
United States
Jennifer P.
The price is CA $224
CA $473 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

6. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is CA $178
CA $266 total
includes taxes & fees
Sep 27 - Sep 28
SteamPunk Bunk House and Intergalactic Way Station
A window with a view of a grassy field and trees.

7. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (6 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is CA $280
CA $432 total
includes taxes & fees
Sep 28 - Sep 29
Spacious, unique barn with beautiful views.
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

8. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"
United States
shawn c b.
The price is CA $247
CA $813 total
includes taxes & fees
Sep 28 - Sep 29
Mohegan Sun Getaway Large Group Retreat
A modern interior with a kitchen, dining area, and living space.

9. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is CA $272
CA $846 total
includes taxes & fees
Sep 28 - Sep 29
6 Beds Home w/Game Room Perfect for Groups
A house with a white porch, a black door, and a window with a white frame.

10. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
The price is CA $346
CA $445 total
includes taxes & fees
Sep 27 - Sep 28
Cozy 1-bedroom cottage in serene Pomfret.
A bedroom with a wooden bed, large windows, and a view of greenery outside.

11. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
The price is CA $354
CA $547 total
includes taxes & fees
Sep 27 - Sep 28
Rustic Farmette Studio with Hot Tub & Pool
A dining area with a high ceiling, skylights, and a view of the outdoors.

12. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (92 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is CA $672
CA $1,097 total
includes taxes & fees
Sep 27 - Sep 28
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

13. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (19 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is CA $120
CA $333 total
includes taxes & fees
Sep 27 - Sep 28
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

14. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (54 reviews)
"Very cute little place to spend a weekend! My friends, partner, and I slept comfortably. The lake itself is very nice (though weather unfortunately prevented us from going out on it with the kayaks) and it is within a short drive to Hartford, UConn, and plenty of things to do. Connecticut is such a lovely state! The purpose of our trip was so that my partner and I could look at apartments in town. We were already excited to move to CT, but after this trip, we became completely confident in how...
United States
Austin R.
The price is CA $189
CA $424 total
includes taxes & fees
Sep 28 - Sep 29
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A lakeside view with a sandy beach, kayaks, and a 'No Dogs' sign.

15. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.0 out of 10, Wonderful, (49 reviews)
"Very peaceful and beautiful area. Well needed relaxing time. Highly recommend! Also Host was exceptional and attentive."
United States
Melissa
The price is CA $212
CA $453 total
includes taxes & fees
Oct 19 - Oct 20
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

16. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is CA $175
CA $456 total
includes taxes & fees
Sep 28 - Sep 29
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A wooden cabin with a balcony and stairs, surrounded by trees.

17. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful farm that’s perfect little getaway for one weekend"
United States
Justyn M.
The price is CA $213
CA $457 total
includes taxes & fees
Sep 27 - Sep 28
Treehouse - Countryside - Farm Animals - Fire Pit
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

18. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is CA $134
CA $259 total
includes taxes & fees
Oct 4 - Oct 5
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A room with a wooden ceiling, a ceiling fan, a blue door, and a dining area with a table and chairs.

19. Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (47 reviews)
"Nice location, just a short walk to the water."
United States
Harris G.
The price is CA $169
CA $398 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

20. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
The price is CA $148
CA $198 total
includes taxes & fees
Sep 29 - Sep 30
The Tiny Cottage & Mini Farm
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windham County Hotel Reviews

Inn on Storrs

Inn on Storrs

10/10 Excellent
"Room was very clean and the staff were super helpful and sweet!"
Madeline 1-night trip
Posted less than an hour ago
Inn on Storrs

Find out more about Windham County

Everything you need to know about Windham County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windham County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham County vacation rentals we have selected for you start as low as CA $153 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windham County rentals

At Expedia, we put the best Windham County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windham County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.