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 two-story house with a front porch, stone steps, and a driveway.

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (9 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
The price is CA $126
CA $244 total
includes taxes & fees
Nov 15 - Nov 16
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
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.

2. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (47 reviews)
"if youre going to sleep 4 here, be aware it'll be a very intimate sleeping situation."
United States
Crystal
The price is CA $180
CA $265 total
includes taxes & fees
Nov 15 - Nov 16
The Tree House at Underhill Hollow
A hotel reception area with a receptionist, a guest, and a child.

3. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
10.0 out of 10, Exceptional, (4 reviews)
"Offers good value with cozy accommodations."
United States
Anonymous traveller
The price is CA $123
CA $142 total
includes taxes & fees
Nov 16 - Nov 17
1 King Bed | Non-Smoking, Micfridge
A red wooden house with a porch, a door with a colorful design, and a green door in the background.

4. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
The price is CA $180
CA $258 total
includes taxes & fees
Nov 15 - Nov 16
Wizard's Roost at Underhill Hollow
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.

5. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is CA $180
CA $258 total
includes taxes & fees
Nov 18 - Nov 19
SteamPunk Bunk House and Intergalactic Way Station
A house with a white porch, a black door, and a window with a white frame.

6. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.2 out of 10, Wonderful, (5 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
The price is CA $307
CA $380 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 1-bedroom cottage in serene Pomfret.
A white building with a green door, surrounded by lush greenery and red autumn leaves.

7. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (11 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 $282
CA $420 total
includes taxes & fees
Nov 16 - Nov 17
Spacious, unique barn with beautiful views.
A wooden deck with a hot tub, a swimming pool, lounge chairs, and a covered area with a railing.

8. 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 $357
CA $529 total
includes taxes & fees
Nov 18 - Nov 19
Rustic Farmette Studio with Hot Tub & Pool
A lakeside dock with a bench and a tree stump nearby.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (95 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 $535
CA $882 total
includes taxes & fees
Nov 15 - Nov 16
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.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (24 reviews)
"The place was unique and cozy. The hosts were very friendly and our stay was great"
United States
Stacy
The price is CA $141
CA $351 total
includes taxes & fees
Nov 23 - Nov 24
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A pond with rocks and a dog in the background.

11. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (14 reviews)
"Love love love this place. A very unique setting on a little farm and the cabin was great. Everything ya need. A gorgeous setting. Tom, the owner is great. Will. Be. Back."
United States
Paul
The price is CA $173
CA $216 total
includes taxes & fees
Nov 15 - Nov 16
The Tiny Cottage & Mini Farm
A wooden cabin with a balcony and stairs, surrounded by trees.

12. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful treehouse with everything you need. My kids loved picking blueberries and meeting the farm animals!"
United States
Lauren B.
The price is CA $185
CA $390 total
includes taxes & fees
Nov 17 - Nov 18
Treehouse - Countryside - Farm Animals - Fire Pit
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

13. 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, (56 reviews)
"Wonderful lake house with a short walk to the beach! Our family of 5 had a wonderful, very relaxing time here."
United States
Blithen D.
The price is CA $178
CA $397 total
includes taxes & fees
Dec 1 - Dec 2
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A large house with a pond and a fountain, surrounded by lush greenery.

14. ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (18 reviews)
"Excellent stay. Saw a concert at Mohegan Sun and was looking for a relaxing day before. Perfect spot."
United States
Geralyn F.
The price is CA $178
CA $453 total
includes taxes & fees
Dec 9 - Dec 10
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
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, (39 reviews)
"Excellent location for a quiet and relaxing getaway. The cabin was clean and well outfitted. Our host greeted us, talked about the history of the property, kayaking around the lake was great, such a good idea for an old youth camp with so much potential. We’ll definitely be returning for another stay"
United States
Zachary C.
The price is CA $250
CA $354 total
includes taxes & fees
Nov 16 - Nov 17
Dove Cabin up in the Trees
A sandy beach with a wooden picnic table and a lake in the background.

16. 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, (50 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 $264
CA $503 total
includes taxes & fees
Dec 9 - Dec 10
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A swimming pool with a white fence and lounge chairs, surrounded by a building with multiple balconies and a tall structure nearby.

17. Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun

Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun
Norwich
8.6 out of 10, Excellent, (33 reviews)
"Good location if you are planning to go to the Mohegan Sun for a show. Enough room for a family of 3."
United States
Jacqueline
The price is CA $209
CA $291 total
includes taxes & fees
Nov 15 - Nov 16
Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun
A patio with outdoor furniture, a covered seating area, and a brick pathway leading to a house with large windows and a chimney.

18. Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Norwich
9.6 out of 10, Exceptional, (70 reviews)
"Beautfil and convenient place. We stayed just one night and the location is perfect since it's just by the Spa."
United States
Aura
The price is CA $195
CA $373 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
A wooden cabin with a glass door, a small pool, and a ceiling fan.

19. 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 $225
CA $433 total
includes taxes & fees
Nov 15 - Nov 16
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
A wooden deck with a hot tub, chairs, and a table by a lake.

20. Lakeside cottage ON the water with beautiful views up the lake!

Lakeside cottage ON the water with beautiful views up the lake!
Ledyard
9.8 out of 10, Exceptional, (216 reviews)
"Perfect spot for a quiet family weekend. Close to mystic restaurants and activities, but removed enough for space and peace. Kayaking, hot tub, playing with all the fish off the dock - perfection!"
United States
Caitlyn G.
The price is CA $189
CA $428 total
includes taxes & fees
Nov 18 - Nov 19
Lakeside cottage ON the water with beautiful views up the lake!
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 biggest bed was great we also liked the breakfast"
Janice 1-night trip
Posted 5 hours 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 $141 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.