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 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.
The price is CA $347
CA $448 total
includes taxes & fees
Oct 15 - Oct 16
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.
The price is CA $179
CA $275 total
includes taxes & fees
Oct 4 - Oct 5
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.
The price is CA $179
CA $266 total
includes taxes & fees
Oct 2 - Oct 3
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.
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.
The price is CA $354
CA $549 total
includes taxes & fees
Oct 4 - Oct 5
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
9.0 out of 10, Wonderful, (41 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 $291
CA $558 total
includes taxes & fees
Oct 1 - Oct 2
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.
The price is CA $179
CA $266 total
includes taxes & fees
Oct 4 - Oct 5
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, (7 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 $281
CA $433 total
includes taxes & fees
Oct 2 - Oct 3
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.
The price is CA $673
CA $1,100 total
includes taxes & fees
Oct 4 - Oct 5
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.
The price is CA $172
CA $311 total
includes taxes & fees
Oct 6 - Oct 7
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.
The price is CA $258
CA $828 total
includes taxes & fees
Oct 1 - Oct 2
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
The price is CA $284
CA $862 total
includes taxes & fees
Oct 1 - Oct 2
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
The price is CA $184
CA $465 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is CA $127
CA $343 total
includes taxes & fees
Oct 1 - Oct 2
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
The price is CA $249
CA $366 total
includes taxes & fees
Oct 1 - Oct 2
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, (46 reviews)
"My girlfriend and I had a wonderful time here it was GREAT.!"
United States
Kareem
The price is CA $223
CA $455 total
includes taxes & fees
Oct 6 - Oct 7
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.
The price is CA $255
CA $465 total
includes taxes & fees
Oct 1 - Oct 2
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
The price is CA $217
CA $503 total
includes taxes & fees
Oct 13 - Oct 14
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.
The price is CA $231
CA $482 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is CA $319
CA $576 total
includes taxes & fees
Oct 1 - Oct 2
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

10/10 Excellent
"The front desk staff was very accommodating."
Christine 1-night trip
Posted less than an hour ago
Two Trees Inn

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 $154 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.