
Vacation rentals in Windham County
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Top-rated vacation rentals in Windham County
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Guest favorite

Cottage in Killingly
4.94 out of 5 average rating, 449 reviewsLake front cottage
AshRating, 5 stars2 months 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 favorite

Apartment in Woodstock
5 out of 5 average rating, 7 reviewsQuiet Corner Studio
MarkRating, 5 stars1 week ago
My wife and I had a great stay at Karin's place for a long weekend in early June. The temperatures outside had gotten warm, but they had the apartment cooled off and comfortable for us. The entire place was clean, the bed was comfortable, and the kitchen was stocked and perfect for our uses. The apartment is easy to access (up a fight of stairs), and located on their property in a lovely area of Connecticut with many adventures in easy driving distance. Karin did a great job communicating with us from the time we reserved the space until after we left. She was proactive, answered any questions we had, and was available during our stay if we needed anything. Though we spent most of our weekend out and about in the area, we were very pleased with our stay in their Quiet Corner Studio apartment. We would happily stay there again.

Guesthouse in Brooklyn
5 out of 5 average rating, 3 reviewsHistoric Railroad Caboose - Unique CT Farm Escape
JennyRating, 5 stars2 weeks ago
This was an amazing place to stay with my three year old! Laurie’s husband came out to show us around the place and my son grabbed his hand right away and was so excited! They had teddy bears and books set up for him and he loved every minute of it! When we woke up the next morning he said “I don’t wanna leave this place!” 10/10 recommend to anyone looking for a cozy getaway!

Cottage in Pomfret
4.95 out of 5 average rating, 38 reviewsLittle House in the Big Woods - Tennis Court
JeanRating, 5 stars8 months ago
We stayed for a wedding held at the Gwyn Careg Inn and The Little House was perfectly located just a few minutes from the wedding venue. This is a beautifully maintained old house with beautiful grounds for strolling. Very warm and inviting living room and dining area. I would say that taller travelers may find the upstairs bedrooms a bit challenging as the sloped roof and old architecture dramatically reduces the headroom in those bedrooms. Not a strike against but something to be aware of…part of the charm of an old home. Just a neat old house and we enjoyed watching Hammer the beagle keeping an eye on things.
Top guest favorite

Private room in Mansfield
5 out of 5 average rating, 101 reviewsWoods Room
LeslieRating, 5 stars1 week ago
Terry and Judy are amazing hosts. They are gracious and friendly but give you space to enjoy being on your schedule in their home. I loved the trees all around, the quiet, joyfully painted room and all the light. The whole house is beautifully painted and so very clean! They provide everything you could need and more. I ended up having breakfast in the kitchen with Judy and an art tour from the two hosts. They have a spectacular collection of art and stories from their adventurous life, which they will share on request. It's a wonderful place to stay.

Guesthouse in Ashford
5 out of 5 average rating, 4 reviewsChez Nanou- Above the Barn Charm
GabrielleRating, 5 stars1 week ago
Was absolutely amazing, Cheryl was incredible with making sure I had what I needed. The location is absolutely gorgeous. Will definitely be back.

Home in Windham
4.96 out of 5 average rating, 140 reviewsmid century home on farmland
AlexandraRating, 5 stars2 months ago
Nothing to say but absolute positivity! Jennifer is amazing! Place was amazing! Experience was amazing! Thanks so much!
Top guest favorite

Barn in Brooklyn
5 out of 5 average rating, 10 reviewsThe Barn at Pondview
KyleRating, 5 stars6 days ago
This was, hands down, the greatest AirBnB our family has ever stayed in. The property was beautiful, well-appointed, and everything was meticulously thought out. Our host proactively reached out to offer an early check-in so our young children could maximize their pool time. And the bar and game room was a great way to spend a rainy day. Would highly recommend and will stay again!
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- Charlestown Beach
- Brown University
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