A town with a prominent church, a river, and autumn foliage.

Cottages in Windham County

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Top Cities in Windham County

A fast-flowing river with a dam and rocky terrain.
CottagesCottages

Putnam

Putnam
A road sign for Brooklyn, Connecticut, with autumn trees in the background.
CottagesCottages

Brooklyn

Brooklyn

Our top choices for Windham County cottages

Exterior

1. 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, (204 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 AED 878
AED 1,612 total
includes taxes & fees
10 Sep - 11 Sep
Lakeside cottage ON the water with beautiful views up the lake!
Exterior detail

2. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 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 AED 900
AED 1,163 total
includes taxes & fees
26 Aug - 27 Aug
Cozy 1-bedroom cottage in serene Pomfret.
Property grounds

3. 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, (233 reviews)
"The kids had a blast fishing off the dock, very clean and comfortable"
United States
katlyn w.
The price is AED 694
AED 1,325 total
includes taxes & fees
27 Aug - 28 Aug
Lakeside cottage overhanging the water, beautiful window views across the lake
Property grounds

4. Peaceful WATERFRONT Cottage Near Mystic and Casinos

Peaceful WATERFRONT Cottage Near Mystic and Casinos
Griswold
9.0 out of 10, Wonderful, (64 reviews)
"We had a wonderful stay. Very peaceful, quiet, beautiful views. We also really enjoyed Hopeville Pond State Park which was only a 5 min drive. "
United States
Jennifer O.
Peaceful WATERFRONT Cottage Near Mystic and Casinos
Smart TV, fireplace

5. Charming 2-bedroom cottage on 7 acres of woods in Putnam with AC, WiFi

Charming 2-bedroom cottage on 7 acres of woods in Putnam with AC, WiFi
Putnam
10.0 out of 10, Exceptional, (13 reviews)
"Nice property close to town friendly owner"
United States
Andrew K.
Charming 2-bedroom cottage on 7 acres of woods in Putnam with AC, WiFi
Exterior

6. Charming Cottage by the Lake❤️

Charming Cottage by the Lake❤️
Coventry Lake
9.4 out of 10, Exceptional, (30 reviews)
"Great place! Would definitely stay again! "
United States
Sam F.
Charming Cottage by the Lake❤️
Exterior

7. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is AED 496
AED 1,118 total
includes taxes & fees
7 Sep - 8 Sep
Lakeview Carriage House with Spectacular Sunset Views
Exterior

8. Private Riverfront w Pool/Hot Tub/Cabins. Sanctuary for Family/Friend Gatherings

Private Riverfront w Pool/Hot Tub/Cabins. Sanctuary for Family/Friend Gatherings
Hopkinton
9.2 out of 10, Wonderful, (91 reviews)
"Great place. We really enjoyed the pool and hot tub. Highly recommend this property. "
United States
Jon H.
Private Riverfront w Pool/Hot Tub/Cabins. Sanctuary for Family/Friend Gatherings
Exterior

9. Brimfield Waterfront cottage

Brimfield Waterfront cottage
Brimfield
10.0 out of 10, Exceptional, (22 reviews)
"The host was wonderful, location was perfectly distanced from Brimfield Flea Market, and the view from the porch was gorgeous! Lovely place to stay. "
United States
Jessica P.
Brimfield Waterfront cottage
Terrace/patio

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

Private Guest House w/ Deck + Spectacular Views!
Montville
10.0 out of 10, Exceptional, (40 reviews)
"I had a pleasant stay, the house is very clean, well-equipped, and the peace and quiet were perfect. I commend the owner."
United States
Faniola O.
Private Guest House w/ Deck + Spectacular Views!
Exterior

11. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (10 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is AED 446
AED 587 total
includes taxes & fees
26 Aug - 27 Aug
The Tiny Cottage & Mini Farm
Exterior

12. Lake Getaway at Coventry Lake! close to Uconn

Lake Getaway at Coventry Lake! close to Uconn
Coventry Lake
10.0 out of 10, Exceptional, (29 reviews)
"Great host, lovely location!"
United States
Christine M.
Lake Getaway at Coventry Lake! close to Uconn
Property grounds

13. Breathtaking Private, Lakefront Retreat.

Breathtaking Private, Lakefront Retreat.
Lebanon
9.0 out of 10, Wonderful, (4 reviews)
"Laurie and Wayne were wonderful hosts. My husband and I had an amazing time celebrating our 28th anniversary. The lake was beautiful, the view was exceptional, and we truly loved being able to use the paddle boards.The house was exactly like the photos—comfortable, cozy, and well cared for. Everything we needed was available, and the space felt like the perfect retreat. If you’re looking to relax, unwind, and enjoy some real tranquility, I highly recommend this place. The peaceful setting is...
United States
Melissa C.
Breathtaking Private, Lakefront Retreat.
Property grounds

14. Weymouth Hill Station. Hillside cottage retreat with water views

Weymouth Hill Station. Hillside cottage retreat with water views
East Greenwich
10.0 out of 10, Exceptional, (43 reviews)
"Very quaint cottage with lots of character, good location between Providence and Newport. Would definitely recommend and stay again"
United States
Robert M.
Weymouth Hill Station. Hillside cottage retreat with water views
Dining

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

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
8.0 out of 10, Very Good, (2 reviews)
"Host was communicative before booking, but communication was not possible other than solely thru this platform. It was difficult to advise the host of my experience or needs. The bedroom rug had a potent urine odor, as well as, being dirty. The toilet was not clean. There is no dishwasher, limited wine glasses and one coffee mug. Though this is a pet-friendly host, the rooms smelled of pet urine. The window A/Cs were not adequately sealed, allowing bugs, moths, and spiders inside the bedroom and...
United States
Liz H.
The price is AED 716
AED 1,284 total
includes taxes & fees
31 Aug - 1 Sep
Privet Farm cottage with AC and Deck in charming Salem Connecticut
Cottage (1 Bedroom) | Interior

16. 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!
1 bedroom, iron/ironing board, WiFi (free), bed sheets

17. Charming Post and Beam Cottage (near Foxwoods)

Charming Post and Beam Cottage (near Foxwoods)
North Stonington
10.0 out of 10, Exceptional, (42 reviews)
"Perfect place to unplug and relax yet close to lots of fun things to do. Cozy, clean, & with luxury amenities. We’ve stayed before and will visit again. We love it there."
United States
Maria C.
Charming Post and Beam Cottage (near Foxwoods)
Exterior

18. Relax with a beautiful lake view

Relax with a beautiful lake view
Colchester
10.0 out of 10, Exceptional, (22 reviews)
"Great location for a getaway or event nearby. Scenic spot and convenient to local spots "
United States
Scott B.
Relax with a beautiful lake view
Terrace/patio

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

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (48 reviews)
"We had a great time swimming and kayaking. The house was spotless. Lake front with great parking."
United States
Christy
The price is AED 477
AED 1,213 total
includes taxes & fees
11 Sep - 12 Sep
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior

20. Charming cottage with short drive to the beach or the city!

Charming cottage with short drive to the beach or the city!
North Kingstown
10.0 out of 10, Exceptional, (19 reviews)
"Charming, clean cottage with ALL the amenities and hosts are super nice and attentive."
United States
Cindy L.
Charming cottage with short drive to the beach or the city!
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

Two Trees Inn

Two Trees Inn

10/10 Excellent
"I apologize for the lengthy review, but I intentionally waited until after multiple stays to write it because I wanted to give the hotel a fair chance and make sure my experience wasn’t based on just one visit. Shockingly, despite the condition of the building, we continued to come back—and there is one reason for that: the incredible staff. I honestly cannot say enough about them. I have rarely seen a staff so genuinely committed to customer service, their guests, and the overall success of a hotel. They consistently go above and beyond and are doing the absolute best they can with a property that desperately needs attention and investment. Unfortunately, the building itself is in serious need of repairs, maintenance, and updating. Across six stays and nine rooms, we have encountered rooms where the air conditioning didn’t work, outlets didn’t work, phones didn’t work, bathroom lights and fans didn’t work, and other basic room functions were not operational. Most importantly, none of the rooms—including my most recent “deluxe” room—had a microwave or a mirror outside the bathroom. We have yet to stay in a room where everything functioned as it should. What makes this particularly frustrating is that this property has so much potential. The staff clearly care and work incredibly hard to compensate for issues that are completely outside of their control. At this point, they are truly the reason to stay here. I sincerely hope ownership invests in the repairs and upgrades this"
Terren 1-night trip
Posted 6 hours ago
Two Trees Inn

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