Windham County Holiday Rentals
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Our top choices for Windham County holiday rentals
1. The Tree House at Underhill Hollow
The Tree House at Underhill HollowThompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
Zachary P.
The price is HK$989
HK$1,527 total
includes taxes & fees
16 Aug - 17 Aug
2. Cozy 1-bedroom cottage in serene Pomfret.
Cozy 1-bedroom cottage in serene Pomfret.Pomfret
10.0 out of 10, Exceptional, (2 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 HK$1,923
HK$2,486 total
includes taxes & fees
16 Aug - 17 Aug
3. 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 HK$989
HK$1,474 total
includes taxes & fees
16 Aug - 17 Aug
4. Stunning Lakefront Escape! Book Your Dream Getaway!
Stunning Lakefront Escape! Book Your Dream Getaway!Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Welcoming host! Beautiful house with great amenities!"
maria c.
The price is HK$3,924
HK$6,338 total
includes taxes & fees
30 Aug - 31 Aug
5. 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."
Kevan W.
The price is HK$1,307
HK$2,099 total
includes taxes & fees
18 Aug - 19 Aug
6. 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!"
Emma S.
The price is HK$3,924
HK$6,338 total
includes taxes & fees
1 Sept - 2 Sept
7. The Carriage House at Chaprae Hall
The Carriage House at Chaprae HallKillingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
Herbert
The price is HK$824
HK$1,571 total
includes taxes & fees
26 Aug - 27 Aug
8. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Lakefront - King - PetsOK - W&D - Fire Pit - KayakAshford
9.2 out of 10, Wonderful, (37 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 HK$1,375
HK$2,719 total
includes taxes & fees
16 Aug - 17 Aug
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
Holiday Inn Express Hotel & Suites Warwick-Providence (Arpt) by IHG
10/10 Excellent
