A river flowing through an urban area with historic buildings and a bridge.

Search Windham Cottage Rentals from CA $195

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Windham cottages

A dining area with a round wooden table surrounded by six white chairs with dark cushions. A potted plant with green foliage and pink flowers is placed in the center.

1. Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
9.0 out of 10, Wonderful, (4 reviews)
"The place was perfect! So much bigger and nicer in person!!!!! Well appointed very cozy! Clean!!!!! Very pet friendly! Great shower!"
United States
Kellie
The price is CA $246
CA $454 total
includes taxes & fees
Oct 26 - Oct 27
Privet Farm cottage with AC and Deck in charming Salem Connecticut
A small white house with black shutters, a porch, and a red barn in the background.

2. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (13 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is CA $145
CA $195 total
includes taxes & fees
Oct 29 - Oct 30
The Tiny Cottage & Mini Farm
A wooden deck with potted plants and a view of a lush landscape.

3. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
3.0 star property
Montville
10.0 out of 10, Exceptional, (3 reviews)
"The pool was amazing, the host was great, very accessible and the property was prisine. The views alone made us immediately want to come back. Very clean and well stocked. "
United States
agata
Private Guest House w/ Deck + Spectacular Views!
A house with a white porch, a black door, and a window with a white frame.

4. 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.
The price is CA $301
CA $390 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 1-bedroom cottage in serene Pomfret.
A wooden deck with potted plants and a view of a lush landscape.

5. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
Montville
10.0 out of 10, Exceptional, (43 reviews)
"Home away from home with one major key asset: Allan, the host is a gem ; extremely welcoming, discreet, hands-on, friendly - very smart so will adapt to the guests. keeps the place a perfect spot to spend few days with family or friends away from the action of the city but very close by car. You are right in the middle of nature (great if you love it), with a wonderful view, an amazingly private large pool (never seen on any rentals before) and a comfortable guesthouse with all the basics you...
United States
pierre g.
Private Guest House w/ Deck + Spectacular Views!
A covered outdoor seating area with wicker furniture, a wooden table, and a bottle of wine.

6. Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!

Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!
Ledyard
10.0 out of 10, Exceptional, (13 reviews)
"My husband and I stayed in the cottage with our fur baby and it was perfect. The cottage was very comfortable and very private."
United States
Kim S.
The price is CA $303
CA $378 total
includes taxes & fees
Oct 26 - Oct 27
Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!
A small, single-story building with a red door and windows, a covered picnic table, and a barbecue grill outside.

7. 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, (212 reviews)
"Sweet, cozy and clean. We had a nice time fishing, spotted a wide variety of birds, and enjoyed a few rounds of croquet. The lake was peaceful and quiet but is only a few minutes from the Foxwoods complex for shopping, dining, casino and shows. Thanks for a great stay!"
United States
Marcy P.
The price is CA $232
CA $482 total
includes taxes & fees
Nov 4 - Nov 5
Lakeside cottage ON the water with beautiful views up the lake!
A deck with a grill, a glass table, and kayaks by a lake.

8. 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, (238 reviews)
"The kids had a blast fishing off the dock, very clean and comfortable"
United States
katlyn w.
The price is CA $224
CA $453 total
includes taxes & fees
Nov 3 - Nov 4
Lakeside cottage overhanging the water, beautiful window views across the lake
A covered outdoor area with a stone patio, a grill, and Adirondack chairs overlooking a forested landscape.

9. Montville Retreat Near Mohegan Sun: 2-home Bundle!

Montville Retreat Near Mohegan Sun: 2-home Bundle!
3.0 star property
Montville
Montville Retreat Near Mohegan Sun: 2-home Bundle!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Great Wolf Lodge Mashantucket

Great Wolf Lodge Mashantucket

10/10 Excellent
"Great family option at Foxwoods"
Brian 1-night trip
Posted 1 hour ago
Great Wolf Lodge Mashantucket

Find out more about Windham

Windham Cottages information

Number of reviews
531
Accommodation
45 Cottages
Lowest Price
CA $195
Highest Price
CA $482

Frequently asked questions

Why book your cottage in Windham with Expedia?
Expedia has some great cottages in Windham, so get set for a memorable vacay close to nature. If you have a fixed budget, click on how much you're willing to spend and the star rating of your property. Or, use our filters to search for cottages with a kitchen or a pool. We'll help you find the perfect pad whatever your style of travel or plans.
How can I find cheap cottages in Windham?
Expedia can help you track down cheap cottages in Windham. To lock in a superb stay in a few clicks, try out our convenient filter tool to refine your search by amenities, budget and star rating.

Explore a world of travel with Expedia