
Holiday rentals in Windham County
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Top-rated holiday rentals in Windham County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Windham County
Guest favourite

Cottage in Killingly
4.94 out of 5 average rating, 448 reviewsLake front cottage
AshRating, 5 stars2 weeks ago
Sarah and I had a beautiful, relaxing stay. The lake was crystal clear and we enjoyed watching the ducks hunt for fish in the morning. The sun floods the space and you have uninterrupted views of the lake. John and Amy have a well stocked home for visitors with spices for cooking, a portable speaker, games, and plenty of cozy sitting options. We are excited to visit again for more kayaking in the warmer months! Thank you both!!
Guest favourite

Home in Thompson
4.9 out of 5 average rating, 101 reviewsWaterfront Cottage on Quaddick Lake, Thompson CT
CynthiaRating, 5 stars6 months ago
Perfect home for the 2 of us and our 2 dogs. The sunrises over the water were amazing! My husband enjoyed some quiet time kayaking and taking in the spectacular views of the changing colors of fall. Great neighborhood for dog walking and friendly neighbors. Jessica was a kind and attentive, responsive host.
Top guest favourite

Home in Hampton
5 out of 5 average rating, 23 reviewsConnecticut Country Escape
MikeRating, 5 stars1 month ago
This home was an absolute gem! Lois was also very responsive and kind throughout the process. Great views and property as well. Would highly recomend !!!
Top guest favourite

Farm stay in Sprague
5 out of 5 average rating, 32 reviewsHanover Vineyards
KarenRating, 5 stars6 months ago
We had a Girls weekend at this beautiful house we had an amazing time! I highly recommend. this house had everything you needed and more we loved lighting a fire and sitting around the fire pit, We will definitely be back!
Guest favourite

Guest suite in Brooklyn
4.92 out of 5 average rating, 183 reviewsAffordable In-Law Apartment in Brooklyn, CT
OmarRating, 5 stars1 month ago
I fell in love with this apartment, the living room, kitchen, bathroom and bedroom were excellent, very cozy and endless amenities, the only complaint I have is the ceiling of the room but it is understandable and is not a big deal and they did not tell us where to put the garbage so we had to leave it in front of the door in the garage but other than that a very good experience in this beautiful place, I recommend it!
Top guest favourite

Flat in Killingly
4.93 out of 5 average rating, 100 reviews2 Bedroom, 1st floor apartment
EfrainRating, 5 stars3 months ago
A very nice place to relax. My reason was because of work in the area. But I was delighted with the place. 100% recommended.
Guest favourite

Home in Mansfield
4.89 out of 5 average rating, 27 reviewsTranquil Forest Haven
JimRating, 5 stars5 months ago
We had a family gathering at Emma's place (Tranquil Forest Haven). Everyone loved it. The house is architecturally unusual in a good way, with an enormous amount of common area for a 4-bedroom home. The kitchen is large enough for several cooks to be working at once and there are two large and one smaller common areas that flow together. The living/dining room has a cathedral ceiling in the sitting area and a lower, flat ceiling in the dining area. The acoustics were great. Even with multiple conversations going everyone could hear each other without shouting. So many homes and other gathering places have bad acoustics for gatherings, so this was a welcome relief from that problem, especially appreciated by the many people in our family who are older, with hearing loss. We had a nice walk around the nearby town pond, next to the school . It is wooded and tranquil, with geese. (The beach is closed due to bacteria. ) We enjoyed the fire in the wood stove.
Guest favourite

Home in Killingly
4.98 out of 5 average rating, 40 reviews"A FOOLS FOLLY FARM"a fun contemporary farmhouse
WilliamRating, 5 stars2 months ago
We wanted a unique stay not too far from home for a brief break in our lackluster winter routine. Ken's farm certainly filled the bill. The best description we can come up with for the house is that it is part antique store, part natural history museum, part collectibles emporium, part library, and part very cozy home! We have never stayed in such an interesting, spacious, comfortable, and well-stocked Airbnb before. Ken is a very personable host who gave us a tour of the home he obviously loves after first having helped us lug our belongings from the truck. He answered questions promptly, kept the walkways clear of snow and ice, gave us fresh eggs from his chickens for breakfast, and had started a welcoming fire in one of the two fireplaces just prior to our arrival. If you are looking for a quiet country setting with a few pleasant surprises, Kenneth's farm is the place to be!
Destinations to explore
- Rentals with a fireplace Windham County
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- Waterfront rentals Windham County
- Rentals with a patio Windham County
- Family-friendly rentals Windham County
- Family-friendly rentals Windham County
- Rentals with lake access Windham County
- Rentals with a kayak Windham County
- Pet-friendly rentals Windham County
- Rentals with a firepit Windham County
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- Charlestown Beach
- Brown University
- Easton Beach
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- Ocean Beach Park
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- Giants Neck Beach
- Blue Shutters Beach
- TPC River Highlands
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- The Breakers
- Grove Beach
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