Vacation Rentals in Windham County

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Top cities in Windham County

Vacation Rentals

Scotland

Scotland

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Windham County vacation rentals

A hotel room with a bed, pillows, a patterned blanket, a bedside table with a lamp, and a wall-mounted phone.

1. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
10.0 out of 10, Exceptional, (4 reviews)
"Offers good value with cozy accommodations."
United States
Anonymous traveler
$87 nightly
The price is $100
Nov 13 - Nov 14
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A two-story wooden house with a deck and a staircase.

2. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
$163 nightly
The price is $186
Nov 15 - Nov 16
Total with taxes and fees
The Tree House at Underhill Hollow
A two-story house with a front porch, stone steps, and a driveway.

3. 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, (9 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
$156 nightly
The price is $177
Nov 13 - Nov 14
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A red wooden house with a porch, a door with a colorful design, and a green door in the background.

4. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
$158 nightly
The price is $180
Nov 15 - Nov 16
Total with taxes and fees
Wizard's Roost at Underhill Hollow
A room with a wall covered in mechanical gears and a bicycle.

5. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$159 nightly
The price is $181
Nov 16 - Nov 17
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
A house with a white porch, a black door, and a window with a white frame.

6. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.2 out of 10, Wonderful, (5 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
$232 nightly
The price is $264
Nov 15 - Nov 16
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
A cozy living room with a bed, a sofa, a small table, and a wall decorated with various posters.

7. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (11 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.
$257 nightly
The price is $293
Nov 14 - Nov 15
Total with taxes and fees
Spacious, unique barn with beautiful views.
A rustic wooden house with a sloped roof, surrounded by a wooden fence and greenery.

8. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
$323 nightly
The price is $368
Nov 13 - Nov 14
Total with taxes and fees
Rustic Farmette Studio with Hot Tub & Pool
A large, two-story house with a prominent brick chimney, a balcony with white railings, and a well-maintained lawn with flowering shrubs.

9. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (95 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$518 nightly
The price is $593
Nov 13 - Nov 14
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A wooden cabin bedroom with a bed, two bedside tables, a wall-mounted lamp, a framed picture, and a window.

10. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (24 reviews)
"The place was unique and cozy. The hosts were very friendly and our stay was great"
United States
Stacy
$237 nightly
The price is $270
Nov 22 - Nov 23
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A wooden cabin with a balcony and stairs, surrounded by trees.

11. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful treehouse with everything you need. My kids loved picking blueberries and meeting the farm animals!"
United States
Lauren B.
$251 nightly
The price is $288
Nov 17 - Nov 18
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (56 reviews)
"Wonderful lake house with a short walk to the beach! Our family of 5 had a wonderful, very relaxing time here."
United States
Blithen D.
$262 nightly
The price is $298
Dec 1 - Dec 2
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A compact kitchen with a refrigerator, a sink, and a window with floral curtains.

13. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (14 reviews)
"Love love love this place. A very unique setting on a little farm and the cabin was great. Everything ya need. A gorgeous setting. Tom, the owner is great. Will. Be. Back."
United States
Paul
$134 nightly
The price is $152
Nov 15 - Nov 16
Total with taxes and fees
The Tiny Cottage & Mini Farm
A bedroom with a bed, bedside tables, a chair, a dresser, and a door.

14. PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (49 reviews)
"Everything was great location, cleanliness, and parking. Enjoyed the stay. Would recommend to anyone looking for a cozy get away!!"
United States
Timothy E.
$298 nightly
The price is $316
Dec 9 - Dec 10
Total with taxes and fees
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
A calm lake with reflections of clouds and a forested hillside.

15. 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, (215 reviews)
"Perfect spot for a quiet family weekend. Close to mystic restaurants and activities, but removed enough for space and peace. Kayaking, hot tub, playing with all the fish off the dock - perfection!"
United States
Caitlyn G.
$266 nightly
The price is $301
Nov 18 - Nov 19
Total with taxes and fees
Lakeside cottage ON the water with beautiful views up the lake!
A living room with a fireplace, a sofa, and a chair.

16. Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Norwich
9.6 out of 10, Exceptional, (69 reviews)
"Beautfil and convenient place. We stayed just one night and the location is perfect since it's just by the Spa."
United States
Aura
$217 nightly
The price is $247
Nov 16 - Nov 17
Total with taxes and fees
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
A spacious living room with a fireplace, leather seating, and large windows.

17. 1 Mi to Mohegan Sun: Studio w/ Pool Access

1 Mi to Mohegan Sun: Studio w/ Pool Access
3.5 star property
Norwich
10.0 out of 10, Exceptional, (2 reviews)
"The space was very clean, the hostess was available, even late night when we needed the code for the gate! "
United States
Sarah
1 Mi to Mohegan Sun: Studio w/ Pool Access
A bedroom with a four-poster bed, a bedside table with a WiFi sign, a brown ottoman, and a decorative mirror on the wall.

18. Cozy Corner, by the Spa

Cozy Corner, by the Spa
Norwich
9.6 out of 10, Exceptional, (13 reviews)
"Beautiful home. Quiet, peaceful & comfortable"
United States
julie
$310 nightly
The price is $330
Nov 18 - Nov 19
Total with taxes and fees
Cozy Corner, by the Spa
A bedroom with a wooden floor, a bed with a blue bedspread, a dresser, a mirror, and a fireplace.

19. ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (18 reviews)
"Nice comfy stay in the beautiful room , Amanda was spot on with everything and very alert with any messages "
United States
Lenny R.
$299 nightly
The price is $318
Dec 9 - Dec 10
Total with taxes and fees
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
A modern kitchen with white cabinets, a black countertop, and stainless steel appliances.

20. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (75 reviews)
"All aspects of our stay were excellent!"
United States
Lori G.
$205 nightly
The price is $233
Nov 16 - Nov 17
Total with taxes and fees
Cozy, comfy,quiet &close to casinos
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

A cozy room with a wooden desk, a comfortable sofa, and a decorative vase on a console table.
The Watson Boutique Bed & Breakfast

The Watson Boutique Bed & Breakfast

The Watson Boutique Bed & Breakfast
Thompson

10/10 Excellent

Great stay and amazing family
United States
Laura
Reviewed August 22, 2026
The Watson Boutique Bed & Breakfast

Frequently Asked Questions

How many vacation rentals are available in Windham County?

Expedia has plenty of vacation rentals to choose from in and around Windham County, so you’re guaranteed to find the right one for you.


How much is a vacation rental in Windham County?

The selection of Windham County vacation rentals we have selected for you start as low as $99 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Windham County?

Vacation rentals in Windham County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Windham County vacation rentals to suit everyone.


Why should I choose a vacation rental in Windham County?

Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Windham County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.


How do I find the best deal on a vacation rental in Windham County?

Find vacation rentals in Windham County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Windham County.


What amenities are available in a vacation rental in Windham County?

The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Windham County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Windham County?

Everytime is a great time to head to Windham County! Staying in a Windham County vacation rentals you will always find lots going on to keep you entertained.


Why book a vacation rental with Expedia?

Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Windham County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Windham County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Windham County, you can save even more.


Can I cancel my vacation rental through Expedia?

Yes, you can cancel or change your Windham County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.


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