Holiday Rentals in Windham County

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Featured Holiday Rentals in Windham County

Exterior
Wizard's Roost at Underhill Hollow

Holiday Home in North Grosvenordale

9.6 out of 10, Exceptional, (21)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
Wizard's Roost at Underhill Hollow
Exterior
The Tree House at Underhill Hollow

Holiday Home in Thompson

9.4 out of 10, Exceptional, (34)
"We had a magical stay! Hosts were accommodating to our needs and eager to make our visit the best."
United States
Grahame E.
The Tree House at Underhill Hollow
Exterior
SteamPunk Bunk House and Intergalactic Way Station

Holiday Home in Thompson

10.0 out of 10, Exceptional, (14)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is €148
includes taxes & fees
15 Dec - 16 Dec
SteamPunk Bunk House and Intergalactic Way Station
Exterior
Charming 2-bedroom apartment in welcoming Putnam

Apartment in Putnam

9.0 out of 10, Wonderful, (2)
"Very nice place. Quiet neighborhood and close to town. "
United States
michael C.
The price is €152
includes taxes & fees
15 Dec - 16 Dec
Charming 2-bedroom apartment in welcoming Putnam
Exterior
The Carriage House at Chaprae Hall

Apartment in Killingly

10.0 out of 10, Exceptional, (30)
"Great stay. Very quiet and convenient for a work event."
United States
sandra P.
The price is €170
includes taxes & fees
4 Jan - 5 Jan 2026
The Carriage House at Chaprae Hall
Interior
Spacious, unique barn with beautiful views.

Holiday Home in Hampton

10.0 out of 10, Exceptional, (3)
"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 €235
includes taxes & fees
9 Dec - 10 Dec
Spacious, unique barn with beautiful views.
Exterior
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Cabin in Ashford

9.2 out of 10, Wonderful, (25)
"Hosted a bachelorette trip at this property and it was fantastic. The kayaks and paddle boards provided plenty to do along with a firepit to sit around at night. The house was cozy with plenty of space to sleep 5. Had a great time! "
United States
Renee J.
The price is €293
includes taxes & fees
10 Dec - 11 Dec
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Outdoor dining
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Holiday Home in Ashford

9.4 out of 10, Exceptional, (19)
"We had a nice getaway after a tour of our alma mater, UCONN. This welcoming and very well decorated home gave us a nice place to rest and connect after our busy day."
United States
Andrea F.
The price is €296
includes taxes & fees
9 Dec - 10 Dec
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Fridge, microwave, oven, stovetop
Stunning Lakefront Escape! Book Your Dream Getaway!

Holiday Home in Woodstock

10.0 out of 10, Exceptional, (21)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
United States
Savanna
The price is €418
includes taxes & fees
7 Dec - 8 Dec
Stunning Lakefront Escape! Book Your Dream Getaway!
Private kitchen
Cozy 1-bedroom cottage in serene Pomfret.

Cottage in Pomfret

2.0 star property
The price is €244
includes taxes & fees
7 Dec - 8 Dec
Cozy 1-bedroom cottage in serene Pomfret.
Exterior
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Holiday Home in Woodstock

9.8 out of 10, Exceptional, (75)
"Lovely stay on the lake, we enjoyed the location and the kayaks on the lake. "
United States
Lucy H.
The price is €433
includes taxes & fees
7 Dec - 8 Dec
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Fridge, microwave, stovetop, coffee/tea maker
Spacious Home Near Mohegan Sun

Holiday Home in Killingly

6.0 out of 10, (2)
"Edgar was very quick to respond to all my inquiries. We stayed here for the weekend. We had eight in our party. We had ample room/beds. The house was very clean and the pictures on website are accurate. There was ample parking. Easy access on and off 395. There are three small things I am going to mention, there were no washcloths (I normally bring loofahs but forgot them) so we had to run to Walmart. The pillows are thin and you would need to use at least two for a comfortable sleep (I always...
United States
Judie T.
The price is €490
includes taxes & fees
7 Dec - 8 Dec
Spacious Home Near Mohegan Sun
4 bedrooms, iron/ironing board, WiFi, bed sheets
Charming 4-bedroom house with WiFi and AC in wonderful Killingly

Holiday Home in Killingly

The price is €718
includes taxes & fees
13 Dec - 14 Dec
Charming 4-bedroom house with WiFi and AC in wonderful Killingly
Property grounds
Glamping with sheep in a renovated 1972 Ace camper on 48 acres

Mobile Home in Cranston

10.0 out of 10, Exceptional, (22)
"Quite relaxing and quiet. Lived the critters! Beautiful property and the owner is amazing!"
United States
heather
The price is €138
includes taxes & fees
31 Dec - 1 Jan 2026
Glamping with sheep in a renovated 1972 Ace camper on 48 acres
Fridge, microwave, oven, stovetop
Charming single family Cottage, pet friendly w fenced in yard,

Cottage in Lincoln

2.0 star property
10.0 out of 10, Exceptional, (20)
"Booked this cozy cottage for a night as we attended a concert at Gillette Stadium. An easy 20 minute drive to and from the stadium. "
United States
Sarah K.
The price is €161
includes taxes & fees
7 Dec - 8 Dec
Charming single family Cottage, pet friendly w fenced in yard,
Property grounds
A Mystic Stay as Sweet as Apple Pie!

Holiday Home in Old Mystic

2.0 star property
10.0 out of 10, Exceptional, (7)
"Loved the personal touches!"
United States
Jenny
The price is €191
includes taxes & fees
15 Dec - 16 Dec
A Mystic Stay as Sweet as Apple Pie!
Terrace/patio
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!

Apartment in Westerly

9.4 out of 10, Exceptional, (11)
"It was sweet, small but roomy for 2.A C was wonderful in the hot day. All provisions served us well. "
United States
Mary Alice B.
The price is €111
includes taxes & fees
21 Dec - 22 Dec
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!
Property grounds
Lakeside cottage ON the water with beautiful views up the lake!

Cottage in Ledyard

9.8 out of 10, Exceptional, (191)
"There were stunning views, it was very relaxing, and we had excellent communication with the host. We couldn’t be happier, it was perfect! Kayaking was the best part. Plenty to see and do in the area as well."
United States
Heather S.
The price is €266
includes taxes & fees
4 Jan - 5 Jan 2026
Lakeside cottage ON the water with beautiful views up the lake!
Outdoor dining
Lakeside cottage overhanging the water, beautiful window views across the lake

Cottage in Ledyard

9.8 out of 10, Exceptional, (217)
"Very comfortable, easy to get to and had everything you could need in a house rental! "
United States
Anna K.
The price is €191
includes taxes & fees
10 Dec - 11 Dec
Lakeside cottage overhanging the water, beautiful window views across the lake
Private kitchen
The Cellar-Suite at Silver LakeNEW 1-Bed APT

Apartment in Silver Lake

2.0 star property
8.0 out of 10, Very good, (4)
"The bed was comfortable, the place was accurate to the description. Not located in the best part of town, but quiet for the most part. The neighbors upstairs were noisy and up all hours of the night. "
United States
Anonymous traveller
The price is €169
includes taxes & fees
6 Jan - 7 Jan 2026
The Cellar-Suite at Silver LakeNEW 1-Bed APT
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

The Loom Hotel, Tapestry Collection by Hilton

The Loom Hotel, Tapestry Collection by Hilton

10/10 Excellent
"Yes, very."
Mark 3-night trip
Posted 2 days ago
The Loom Hotel, Tapestry Collection by Hilton

Find out more about Windham County

Holiday Homes in Windham County

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