Windham County Holiday Rentals

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Top Holiday Rentals Destinations in Windham County

The Tree House at Underhill Hollow
Exterior

The Tree House at Underhill Hollow

9.4 out of 10, Exceptional, (32)
"My 10 year old loved this stay! Meeting the goats and sheep was fun and it was located in a nice area. Would love to visit again!"
The price is AU$267
includes taxes & fees
13 Oct - 14 Oct
The Tree House at Underhill Hollow
Wizard's Roost at Underhill Hollow
Exterior

Wizard's Roost at Underhill Hollow

9.6 out of 10, Exceptional, (18)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
The price is AU$242
includes taxes & fees
13 Oct - 14 Oct
Wizard's Roost at Underhill Hollow
The Cellar-Suite at Silver LakeNEW 1-Bed APT
Private kitchen

The Cellar-Suite at Silver LakeNEW 1-Bed APT

2.0 star property
9.0 out of 10, Wonderful, (2)
"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. "
The price is AU$290
includes taxes & fees
14 Oct - 15 Oct
The Cellar-Suite at Silver LakeNEW 1-Bed APT
The Micro-Loft at Mt. Pleasant New 2BR APT Parking
2 bedrooms, iron/ironing board, WiFi, bed sheets

The Micro-Loft at Mt. Pleasant New 2BR APT Parking

2.0 star property
7.0 out of 10, Good, (6)
"It was clean and met our needs for the visit."
The price is AU$250
includes taxes & fees
20 Oct - 21 Oct
The Micro-Loft at Mt. Pleasant New 2BR APT Parking
Lakeside cottage overhanging the water, beautiful window views across the lake
Outdoor dining

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

9.8 out of 10, Exceptional, (210)
"Nice home and location, included amenities very nice. "
The price is AU$581
includes taxes & fees
4 Nov - 5 Nov
Lakeside cottage overhanging the water, beautiful window views across the lake
Treehouse - Countryside - Farm Animals - Fire Pit
Property grounds

Treehouse - Countryside - Farm Animals - Fire Pit

9.4 out of 10, Exceptional, (27)
"Safe, inviting stay."
The price is AU$445
includes taxes & fees
13 Oct - 14 Oct
Treehouse - Countryside - Farm Animals - Fire Pit
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

9.8 out of 10, Exceptional, (25)
"This prperty was GREAT! Clean, and very accomadating. Had everything you would need staying there. Didn't get to use the lake but sitting on the deck was relaxing. Will book again. 10 Stars!! Thank You!"
The price is AU$476
includes taxes & fees
14 Oct - 15 Oct
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Lakeside cottage ON the water with beautiful views up the lake!
Property grounds

Lakeside cottage ON the water with beautiful views up the lake!

9.8 out of 10, Exceptional, (186)
"every was very easy process and a pleasure to stay there"
The price is AU$564
includes taxes & fees
11 Nov - 12 Nov
Lakeside cottage ON the water with beautiful views up the lake!
Dove Cabin up in the Trees
Exterior

Dove Cabin up in the Trees

9.8 out of 10, Exceptional, (25)
"A sweet, cozy, nostalgic little cabin in the woods. It was the perfect stop over on our road trip to Acadia. Very peaceful, and the screened in porch was wonderful to relax on before bed and during breakfast. "
The price is AU$397
includes taxes & fees
12 Oct - 13 Oct
Dove Cabin up in the Trees
Spacious 7-bedroom house Stonington with amazing views.
Dining

Spacious 7-bedroom house Stonington with amazing views.

10.0 out of 10, Exceptional, (5)
"The place is lovely! I stayed here for the week leading up to my wedding with my whole family and we had a great time! The host and his wife went ABOVE and BEYOND to be helpful and (no joke) saved my wedding dress! Definitely stay here."
Spacious 7-bedroom house Stonington with amazing views.
SECLUDED WATERFRONT HOME WITH ROOM FOR ALL
Terrace/patio

SECLUDED WATERFRONT HOME WITH ROOM FOR ALL

9.8 out of 10, Exceptional, (44)
"We had a blast! Thanks again. "
SECLUDED WATERFRONT HOME WITH ROOM FOR ALL
Humble Beginnings
Exterior

Humble Beginnings

10.0 out of 10, Exceptional, (5)
"We loved this property.Only stayed one night, wish we could spend more time here. Well stocked kitchen, bathroom extras in case you've forgotten some essentials at home. Electric fireplace for that special atmosphere while hanging out in the living room. Super comfy mattresses. Shower with great water pressure and extra large head. Convenient access, private parking space. Board games. Books. Quiet air purifiers in each room.I could go on and on.Definitely will stay again. Adding to favorites."
The price is AU$282
includes taxes & fees
13 Oct - 14 Oct
Humble Beginnings
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!
Terrace/patio

Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!

9.4 out of 10, Exceptional, (8)
"Great spot, easy check-in and out, coffee, creamer, and sugar, snacks and water! Would recommend this for a 1/2 person stay! Great price!"
The price is AU$192
includes taxes & fees
13 Oct - 14 Oct
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!
Lovely Historic Vintage home. Remodeled inside.
Dining

Lovely Historic Vintage home. Remodeled inside.

9.2 out of 10, Wonderful, (36)
"Overall it was ok. Quaint and quiet neighborhood. Nice area for a little get away"
The price is AU$737
includes taxes & fees
14 Oct - 15 Oct
Lovely Historic Vintage home. Remodeled inside.
Casino Getaway! 2M from Mohegan 8M from Foxwoods
Terrace/patio

Casino Getaway! 2M from Mohegan 8M from Foxwoods

6.0 out of 10, (1)
"Elliot was available and courteous reservation and check in easy. Upon arrival 1st floor bathroom sink was not draining well, 2nd floor bathroom tub does not drain well hot and cold water are reversed sink water is also reversed. Missing sheet rock in dining room. All walls have either nails popping or water damage. We only slept at the residence one evening. I manage multiple high end properties on Nantucket and maintaining them year round. First impression is Most important to insure future...
The price is AU$388
includes taxes & fees
14 Oct - 15 Oct
Casino Getaway! 2M from Mohegan 8M from Foxwoods
Your Charming 4BR Retreat Home Minutes from Casino Excitement!
Private kitchen

Your Charming 4BR Retreat Home Minutes from Casino Excitement!

9.8 out of 10, Exceptional, (8)
"Had a wonderful weekend"
The price is AU$1,500
includes taxes & fees
14 Oct - 15 Oct
Your Charming 4BR Retreat Home Minutes from Casino Excitement!
Lakeside Haven at the Pines / Tent
Property grounds

Lakeside Haven at the Pines / Tent

9.0 out of 10, Wonderful, (7)
"My family and I had a great time. Canoeing, making s’mores in the fire pit, grilling, and amazing bike rides. We made great memories there that we will never forget!!"
The price is AU$234
includes taxes & fees
14 Oct - 15 Oct
Lakeside Haven at the Pines / Tent
Thames River Retreat · CT College+Casinos+USCGA
Property grounds

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (17)
"Clean"
The price is AU$901
includes taxes & fees
10 Nov - 11 Nov
Thames River Retreat · CT College+Casinos+USCGA
Peaceful WATERFRONT Cottage Near Mystic and Casinos
Fridge, microwave, oven, stovetop

Peaceful WATERFRONT Cottage Near Mystic and Casinos

9.2 out of 10, Wonderful, (54)
"It was a great stay. Good space. A great place to come back to after exploring Connecticut for a few days. The pond access and kayaks were a great bonus "
Peaceful WATERFRONT Cottage Near Mystic and Casinos
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Property grounds

Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

8.4 out of 10, Very good, (11)
"Affordable, fun, relaxing house. Indoor and outdoor things to do. Some pretty glass decor in the dining room, so I easily moved a few things to temporarily kid proof it. A/C in bedrooms, ceiling fans in almost every room. The hosts were very responsive and addressed our concerns exceptionally well."
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
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

Cedar Park Whirlpool Suites

Cedar Park Whirlpool Suites

10/10 Excellent
"Everything was very clean "
Greg 1-night trip
Posted 1 day ago
Cedar Park Whirlpool Suites

Find out more about Windham County

Everything you need to know about Windham County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windham County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windham County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Windham County holiday rentals we have chosen for you start as low as AU$192 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Windham County rentals

At Expedia, we put the best Windham County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windham County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.