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

Vacation Rentals in Windham County

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Top Cities in Windham County

A church with a steeple, a bridge, and a bench in a park.
Vacation RentalsVacation Rentals

Willimantic

Willimantic

Our top choices for Windham County vacation rentals

A house with a white porch, a black door, and a window with a white frame.

1. 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.
$265 nightly
The price is $302
Sep 28 - Sep 29
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
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.
$171 nightly
The price is $194
Sep 28 - Sep 29
Total with taxes and fees
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

3. 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.
$166 nightly
The price is $188
Sep 28 - Sep 29
Total with taxes and fees
Wizard's Roost at Underhill Hollow
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.
$287 nightly
The price is $327
Sep 28 - Sep 29
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A bedroom with a wooden bed, large windows, and a view of greenery outside.

5. 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.
$320 nightly
The price is $365
Sep 28 - Sep 29
Total with taxes and fees
Rustic Farmette Studio with Hot Tub & Pool
A small, single-story cabin with a porch and a small deck, surrounded by trees and a lake.

6. 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.
$274 nightly
The price is $312
Sep 30 - Oct 1
Total with taxes and fees
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.

7. 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.
$166 nightly
The price is $188
Sep 28 - Sep 29
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
A window with a view of a grassy field and trees.

8. 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.
$258 nightly
The price is $294
Oct 1 - Oct 2
Total with taxes and fees
Spacious, unique barn with beautiful views.
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$640 nightly
The price is $730
Oct 4 - Oct 5
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A two-story house with a front porch, stone steps, and a driveway.

10. 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.
$192 nightly
The price is $217
Oct 6 - Oct 7
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

11. 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.
$452 nightly
The price is $543
Sep 28 - Sep 29
Total with taxes and fees
Mohegan Sun Getaway Large Group Retreat
A modern interior with a kitchen, dining area, and living space.

12. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
$472 nightly
The price is $566
Sep 28 - Sep 29
Total with taxes and fees
6 Beds Home w/Game Room Perfect for Groups
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

13. 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
$267 nightly
The price is $304
Sep 28 - Sep 29
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

14. 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
$204 nightly
The price is $232
Sep 28 - Sep 29
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A wooden cabin with a glass upper floor, surrounded by a forest.

15. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
$236 nightly
The price is $249
Sep 28 - Sep 29
Total with taxes and fees
Dove Cabin up in the Trees
A wooden cabin with a glass door, a small pool, and a ceiling fan.

16. Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Norwich
10.0 out of 10, Exceptional, (45 reviews)
"My girlfriend and I had a wonderful time here it was GREAT.!"
United States
Kareem
$268 nightly
The price is $305
Sep 28 - Sep 29
Total with taxes and fees
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
A parking lot with several cars and a modern building with glass windows in the background.

17. Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (42 reviews)
"My return visite excellent place to stay."
United States
Lisa M.
$276 nightly
The price is $314
Sep 28 - Sep 29
Total with taxes and fees
Peaceful Oasis Steps from Mohegan Sun
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

18. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
9.6 out of 10, Exceptional, (9 reviews)
"This is a real gem of a find! I loved our stay here. GPS does take you to the back of the building but it’s located next to a large parking lot. Plenty of parking which was great for us because we have an extended cab f350 ford that does not fit into most parking spaces. The other great thing about this house is multiple showers and bathrooms. This is so rare in a CT house. I must’ve searched for hours. The host Pam was super friendly and was so quick to respond. The house was super stocked with...
United States
Jenny
$301 nightly
The price is $343
Sep 28 - Sep 29
Total with taxes and fees
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A wooden cabin with a balcony and stairs, surrounded by trees.

19. 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.
$284 nightly
The price is $324
Oct 20 - Oct 21
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
A modern bedroom with a bed, a sofa, a small table, and a TV on the wall.

20. The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun

The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (10 reviews)
"Nice alternative to hotel … after casino show ….would definitely come back !"
United States
Andrew
$341 nightly
The price is $388
Sep 28 - Sep 29
Total with taxes and fees
The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun
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

Two Trees Inn

Two Trees Inn

8/10 Good
"Bathrooms need a little upgrade."
Deborah 2-night trip
Posted less than an hour ago
Two Trees Inn

Find out more about Windham County

Discover your perfect Windham County vacation rental with Expedia

How many vacation rentals are available in Windham County?


Expedia has plenty of vacation rentals to choose from in and around  Windham County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Windham County?


The selection of Windham County vacation rentals we have selected for you start as low as $108 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Windham County?


Vacation rentals in Windham County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Windham County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Windham County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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. 


How do I find the best deal on a vacation rental in Windham County?


Find vacation rentals in Windham County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Windham County.  


What amenities are available in a vacation rental in Windham County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Windham County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Windham County?   


Everytime is a great time to head to Windham County! Staying in a Windham County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Windham County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Windham County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Windham County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Windham County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.  


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