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

Holiday Rentals in Windham County

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Our top choices for Windham County holiday rentals

Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is €175
includes taxes & fees
2 Aug - 3 Aug
The Tree House at Underhill Hollow
Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Great experience. Thank you "
United States
edmund d.
The price is €663
includes taxes & fees
2 Aug - 3 Aug
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (87 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is €686
includes taxes & fees
2 Aug - 3 Aug
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (36 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
The price is €363
includes taxes & fees
30 Jul - 31 Jul
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Exterior detail

Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (1 review)
"We were up in Pomfret for a wedding in the area. Perfect location for us; walkable to a local cafe (Vanilla Bean) for breakfast. The place sits on a large piece of property complete with pond; beautiful setting, very peaceful. Plenty of space for parking; water pressure was great for showers and appreciate the travel size lotions, shampoo, etc ! Overall a great experience. Would highly recommend, especially for parents of students who attend The Pomfret School (boarding). Perfect location...
United States
Stephanie K.
The price is €285
includes taxes & fees
26 Aug - 27 Aug
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 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 €169
includes taxes & fees
2 Aug - 3 Aug
Wizard's Roost at Underhill Hollow
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (5 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 €237
includes taxes & fees
30 Jul - 31 Jul
Spacious, unique barn with beautiful views.
Exterior

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, (5 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 €240
includes taxes & fees
5 Aug - 6 Aug
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is €169
includes taxes & fees
2 Aug - 3 Aug
SteamPunk Bunk House and Intergalactic Way Station
Exterior

The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
The price is €183
includes taxes & fees
26 Aug - 27 Aug
The Carriage House at Chaprae Hall
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (22 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is €398
includes taxes & fees
18 Aug - 19 Aug
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Coffee/tea maker, fridge, microwave, oven

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 €613
includes taxes & fees
29 Jul - 30 Jul
Mohegan Sun Getaway Large Group Retreat
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is €619
includes taxes & fees
29 Jul - 30 Jul
6 Beds Home w/Game Room Perfect for Groups
Property grounds

The Ultimate Luxury Coastal Houseboat Experience at Jodoin Marina -Sleeps 4!

The Ultimate Luxury Coastal Houseboat Experience at Jodoin Marina -Sleeps 4!
East Greenwich
10.0 out of 10, Exceptional, (4 reviews)
"Amazing experience; all the space we needed, beautiful surroundings. Clean, all the amenities, we (and our pup) LOVED it! Close to GREAT restaurants! If you need to relax, do yourself a favor and book this slice of heaven."
United States
Christopher M.
The price is €591
includes taxes & fees
13 Aug - 14 Aug
The Ultimate Luxury Coastal Houseboat Experience at Jodoin Marina -Sleeps 4!
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (32 reviews)
"Sue is a great host, making necessary adjustments to suit the circumstances, generous and flexible. The dove cabin is so sweet, comfortable beds, cozy stove and fully equipped kitchen. And lovely porch! There’s a really cool swing on the way down to a peaceful pond!"
United States
kathryn m.
The price is €234
includes taxes & fees
29 Jul - 30 Jul
Dove Cabin up in the Trees
A row of colorful kayaks lined up on a grassy shore by a lake, with a wooden dock extending into the water.

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
9.8 out of 10, Exceptional, (158 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
The price is €341
includes taxes & fees
20 Aug - 21 Aug
Go Jump in the Lake!
Beach nearby

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.2 out of 10, Wonderful, (46 reviews)
"The property was clean and accommodating."
United States
Ann Marie T.
The price is €332
includes taxes & fees
2 Aug - 3 Aug
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Exterior

Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (38 reviews)
"Nice stay"
United States
WINFOR
The price is €294
includes taxes & fees
29 Jul - 30 Jul
Peaceful Oasis Steps from Mohegan Sun
Smart TV

The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (9 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is €165
includes taxes & fees
29 Jul - 30 Jul
The Tiny Cottage & Mini Farm
Smart TV

3 bed apartment, 5 mi to Mohegan/10 to Foxwoods

3 bed apartment, 5 mi to Mohegan/10 to Foxwoods
Laurel Hill
9.6 out of 10, Exceptional, (44 reviews)
"Enjoyed our stay, plenty of room and quiet. Had everything we needed and more. I will rent again for sure."
United States
chad m.
The price is €163
includes taxes & fees
29 Jul - 30 Jul
3 bed apartment, 5 mi to Mohegan/10 to Foxwoods
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
"Very clean rooms and facilities. Spacious rooms, and enjoyed the indoor pool and hot tub. The staff were friendly and it was a great location, being close to the casino. There was also a free shuttle service offered, along with continental breakfast. The lady taking care of the breakfast lady was very attentive and friendly. Overall a good stay."
Ashley 1-night trip
Posted 2 hours ago
Two Trees Inn

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Holiday Homes in Windham County

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