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 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Windham County vacation rentals

Dining Room

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
$88 nightly
The price is $101
Nov 11 - Nov 12
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. 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 8 - Nov 9
Total with taxes and fees
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

3. 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 6 - Nov 7
Total with taxes and fees
The Tree House at Underhill Hollow
A two-story house with a front porch, stone steps, and a driveway.

4. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
$171 nightly
The price is $196
Nov 9 - Nov 10
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

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.
$158 nightly
The price is $180
Nov 8 - Nov 9
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 8 - Nov 9
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
A bedroom with a wooden bed, large windows, and a view of greenery outside.

7. 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 8 - Nov 9
Total with taxes and fees
Rustic Farmette Studio with Hot Tub & Pool
A window with a view of a grassy field and trees.

8. 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 8 - Nov 9
Total with taxes and fees
Spacious, unique barn with beautiful views.
A dining area with a high ceiling, skylights, and a view of the outdoors.

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.
$543 nightly
The price is $618
Nov 7 - Nov 8
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (23 reviews)
"The place was unique and cozy. The hosts were very friendly and our stay was great"
United States
Stacy
$203 nightly
The price is $232
Nov 16 - Nov 17
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A pond with rocks and a dog in the background.

11. 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 8 - Nov 9
Total with taxes and fees
The Tiny Cottage & Mini Farm
A wooden cabin with a balcony and stairs, surrounded by trees.

12. 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.
$239 nightly
The price is $272
Nov 9 - Nov 10
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
A hammock in a lush garden with a house in the background.

13. A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (13 reviews)
"The place was perfect and the vibe was awesome. The hosts think of everything!"
United States
Matt F.
$187 nightly
The price is $213
Nov 30 - Dec 1
Total with taxes and fees
A Mystic Stay as Sweet as Apple Pie!
A swimming pool with a wooden deck area, a covered seating area, and a building with a clock.

14. 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
$295 nightly
The price is $313
Dec 1 - Dec 2
Total with taxes and fees
Cozy Corner, by the Spa
A dock with a chair and a red canoe, overlooking a calm lake at sunset.

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, (214 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.
$263 nightly
The price is $298
Nov 8 - Nov 9
Total with taxes and fees
Lakeside cottage ON the water with beautiful views up the lake!
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

16. 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, (55 reviews)
"Very cute little place to spend a weekend! My friends, partner, and I slept comfortably. The lake itself is very nice (though weather unfortunately prevented us from going out on it with the kayaks) and it is within a short drive to Hartford, UConn, and plenty of things to do. Connecticut is such a lovely state! The purpose of our trip was so that my partner and I could look at apartments in town. We were already excited to move to CT, but after this trip, we became completely confident in how...
United States
Austin R.
$229 nightly
The price is $261
Nov 8 - Nov 9
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A large house with a pond and a fountain, surrounded by lush greenery.

17. 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.
$285 nightly
The price is $304
Nov 9 - Nov 10
Total with taxes and fees
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
A boat yard with several boats docked, a building labeled "Boat Yard," and a reflection in the water.

18. Entire Private 1 bedroom apartment ✨XL bathroom💄👔✨Breakfast included🥞

Entire Private 1 bedroom apartment ✨XL bathroom💄👔✨Breakfast included🥞
Greeneville
10.0 out of 10, Exceptional, (10 reviews)
"Our stay here was for an overnight trip, it exceedee our expectations. It was cute, cozy, excellently maintained. It has a little charm to it and the continental breakfast was a nice touch by the host. Definitely would book again for trip. "
United States
Frank M.
$155 nightly
The price is $176
Nov 8 - Nov 9
Total with taxes and fees
Entire Private 1 bedroom apartment ✨XL bathroom💄👔✨Breakfast included🥞
A patio with outdoor furniture, a covered seating area, and a brick pathway leading to a house with large windows and a chimney.

19. 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
$210 nightly
The price is $240
Nov 17 - Nov 18
Total with taxes and fees
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
A gazebo with wicker furniture and a sign indicating it's open.

20. 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, (51 reviews)
"Definitely recommend to travelers seeking quaint, relaxing, convenient lodging in the Old Mystic, CT area."
United States
Kirsten K.
$154 nightly
The price is $176
Nov 9 - Nov 10
Total with taxes and fees
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
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 hallway with a fireplace, a wreath on the door, and a wooden floor.
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 $100 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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