Holiday Rentals in Windham County
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Our top choices for Windham County holiday rentals
1. Secluded 2-Acre Lakefront Home! Book Your Getaway!
Secluded 2-Acre Lakefront Home! Book Your Getaway!Woodstock
9.8 out of 10, Exceptional, (89 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
Emma S.
The price is €660
includes taxes & fees
15 Sept - 16 Sept
2. Stunning Lakefront Escape! Book Your Dream Getaway!
Stunning Lakefront Escape! Book Your Dream Getaway!Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"We loved our stay at this lakeside retreat. We were in town for a wedding and in between family gatherings we were able to relax by the lake. The house was comfortable and well stocked so we didn't have to buy every little thing. I would definitely stay again"
Lisa R.
The price is €637
includes taxes & fees
24 Sept - 25 Sept
3. The Tree House at Underhill Hollow
The Tree House at Underhill HollowThompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
Douglas C.
The price is €170
includes taxes & fees
14 Sept - 15 Sept
4. Wizard's Roost at Underhill Hollow
Wizard's Roost at Underhill HollowNorth 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. "
Mateo A.
The price is €165
includes taxes & fees
17 Sept - 18 Sept
5. 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."
Kevan W.
The price is €266
includes taxes & fees
23 Sept - 24 Sept
6. Cozy 1-bedroom cottage in serene Pomfret.
Cozy 1-bedroom cottage in serene Pomfret.Pomfret
8.8 out of 10, Excellent, (3 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
Aaron H.
The price is €278
includes taxes & fees
14 Sept - 15 Sept
7. SteamPunk Bunk House and Intergalactic Way Station
SteamPunk Bunk House and Intergalactic Way StationThompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
Pauline S.
The price is €166
includes taxes & fees
13 Sept - 14 Sept
8. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Lakefront - King - PetsOK - W&D - Fire Pit - KayakAshford
9.2 out of 10, Wonderful, (39 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. "
Jennifer P.
The price is €253
includes taxes & fees
13 Sept - 14 Sept
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
Hyatt Place Uncasville - Casino Area
10/10 Excellent
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Holiday Homes in Windham County
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