Windham County Holiday Rentals

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Featured Windham County Holiday Rentals

Exterior
Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow

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.
The price is HK$771
HK$1,221 total
includes taxes & fees
14 Dec - 15 Dec
Wizard's Roost at Underhill Hollow
Exterior
SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station

Thompson
10.0 out of 10, Exceptional, (14)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is HK$841
HK$1,302 total
includes taxes & fees
14 Dec - 15 Dec
SteamPunk Bunk House and Intergalactic Way Station
Exterior
Charming 2-bedroom apartment in welcoming Putnam

Charming 2-bedroom apartment in welcoming Putnam

Putnam
9.0 out of 10, Wonderful, (2)
"Very nice place. Quiet neighborhood and close to town. "
United States
michael C.
The price is HK$645
HK$1,345 total
includes taxes & fees
15 Dec - 16 Dec
Charming 2-bedroom apartment in welcoming Putnam
Exterior
The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall

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 HK$778
HK$1,506 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Carriage House at Chaprae Hall
Interior
Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.

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 HK$1,296
HK$2,059 total
includes taxes & fees
10 Dec - 11 Dec
Spacious, unique barn with beautiful views.
Fridge, microwave, oven, stovetop
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

Windham
9.8 out of 10, Exceptional, (8)
"Great house for family visit with our USCG cadet. The owners were very flexible and responsive to our needs. The property was clean and spacious we will use again! "
United States
Mark M.
The price is HK$1,207
HK$4,330 total
includes taxes & fees
15 Dec - 16 Dec
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Exterior
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

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

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 HK$1,230
HK$2,567 total
includes taxes & fees
9 Dec - 10 Dec
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Fridge, microwave, oven, stovetop
Home with King Bed Near UCONN & ECSU & Hospital

Home with King Bed Near UCONN & ECSU & Hospital

Prospect Hill Historic District
The price is HK$1,242
HK$2,603 total
includes taxes & fees
29 Dec - 30 Dec
Home with King Bed Near UCONN & ECSU & Hospital
Outdoor dining
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

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

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 HK$1,277
HK$2,628 total
includes taxes & fees
9 Dec - 10 Dec
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Private kitchen
Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.

2.0 star property
Pomfret
The price is HK$1,713
HK$2,164 total
includes taxes & fees
8 Dec - 9 Dec
Cozy 1-bedroom cottage in serene Pomfret.
Fridge, microwave, oven, stovetop
Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

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 HK$1,927
HK$3,708 total
includes taxes & fees
8 Dec - 9 Dec
Stunning Lakefront Escape! Book Your Dream Getaway!
Exterior
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

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 HK$2,034
HK$3,847 total
includes taxes & fees
8 Dec - 9 Dec
Secluded 2-Acre Lakefront Home! Book Your Getaway!
4 bedrooms, iron/ironing board, WiFi, bed sheets
Charming 4-bedroom house with WiFi and AC in wonderful Killingly

Charming 4-bedroom house with WiFi and AC in wonderful Killingly

Killingly
The price is HK$2,662
HK$6,359 total
includes taxes & fees
14 Dec - 15 Dec
Charming 4-bedroom house with WiFi and AC in wonderful Killingly
Fridge, microwave, stovetop, coffee/tea maker
Spacious Home Near Mohegan Sun

Spacious Home Near Mohegan Sun

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 HK$1,457
HK$4,350 total
includes taxes & fees
8 Dec - 9 Dec
Spacious Home Near Mohegan Sun
Property grounds
Glamping with sheep in a renovated 1972 Ace camper on 48 acres

Glamping with sheep in a renovated 1972 Ace camper on 48 acres

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 HK$778
HK$1,219 total
includes taxes & fees
31 Dec - 1 Jan 2026
Glamping with sheep in a renovated 1972 Ace camper on 48 acres
Property grounds
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, (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 HK$679
HK$1,871 total
includes taxes & fees
10 Dec - 11 Dec
Lakeside cottage ON the water with beautiful views up the lake!
Property grounds
A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!

2.0 star property
Old Mystic
10.0 out of 10, Exceptional, (7)
"Loved the personal touches!"
United States
Jenny
The price is HK$796
HK$1,677 total
includes taxes & fees
8 Dec - 9 Dec
A Mystic Stay as Sweet as Apple Pie!
Property grounds
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

Old Mystic
10.0 out of 10, Exceptional, (33)
"Absolutely adorable! Beautiful view from our window. Quaint decor and every little detail thought of. Loved our stay! "
United States
Randolph
The price is HK$694
HK$1,543 total
includes taxes & fees
23 Dec - 24 Dec
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Outdoor dining
Lakeside cottage overhanging the water, beautiful window views across the lake

Lakeside cottage overhanging the water, beautiful window views across the lake

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 HK$617
HK$1,694 total
includes taxes & fees
10 Dec - 11 Dec
Lakeside cottage overhanging the water, beautiful window views across the lake
Property grounds
Cozy apartment along the Wood River in the heart of Richmond.

Cozy apartment along the Wood River in the heart of Richmond.

Richmond
9.4 out of 10, Exceptional, (3)
"Property.\nWas absolutely gorgeous.The river was beautiful, quiet and peaceful.Very pet friendly immaculate , and shopping was just right down the street"
United States
Lisa C.
The price is HK$743
HK$1,853 total
includes taxes & fees
10 Dec - 11 Dec
Cozy apartment along the Wood River in the heart of Richmond.
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Yes"
Chris 1-night trip
Posted 22 hours ago
Wellsworth Hotel