
Vacation rentals in Windsor
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Top-rated vacation rentals in Windsor
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Popular amenities for Windsor vacation rentals
Other great vacation rentals in Windsor

Beautiful home walking distance to Ocean Beach
A great setting for a large family gathering. Lots for everyone in the family to do from the kids to the grandparents. The kids especially loved the puppets and playing hide and seek in the house. Tony was flexible with check in as our flight arrived earlier than originally expected. Would highly recommend 😊

Writer's retreat: study, books, fireplace (Ecobnb)
The location and space were great! I worked remotely during most of my stay and was very comfortable with my set up. The dining table was a perfect desk, with good lighting and wifi! Slept well due to it being so quiet at night. A positive experience overall.

Lake house retreat Granby CT
We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!

Spacious Classic Lakefront Home with jet tub
I came here in the dead of winter for a writer's retreat with a fellow writer- AND I WOULD DO IT AGAIN! It was a beautiful and inspiring place to write. Perched on Andover Lake, it was too cold to frolic outside but that was actually liberating. There was a rocking chair-ottoman combo in the master bedroom looking out on the lake and watching it freeze while I worked on some writing was so peaceful and perfect. When I needed to switch it up, there was a writer's desk with the same view and I can not overstate how nice and productive it was to work from it. I am sure in the summer it's a really fun stay (there were kayaks and a dock for swimming) but I actually loved being isolated in such an idyllic place. It's near a few other homes but the road was low traffic enough for a cold weather run around half the lake. Marcie was super helpful with suggestions for places to eat. We didn't actually use the recs - but that only speaks to how nice the house was and how hard it was to leave!

Casa Lago
I didnt want to leave this little cabin in the woods. It felt rustic but had all the modern amenities you would expect in a home. From the rocking chairs on the porch to the comfy beds, there is nothing I could complain about, even if I tried. Marilyn gave excellent suggestions of places to eat and local current events. We left with fall apples, bellies full of clam chowder, and gigantic smiles!!! We have already started planning our return!

The Pinnacle House at Otis Ridge Ski Area!
Welcoming, tidy and clean home. Fully functional and amenable to families with young children. A perfect winter getaway spot given its proximity to Otis Ridge. Extremely easy to ski in and ski out. Mary Kay is a lovely host- extremely responsive, helpful and flexible.

Villa with Access to Amazing Amenities!
The place was great and wish i had more time there. We were just looking for a quick overnight with two bedrooms, which this was, but it seemed like a lovely place for a vacation.

Pet Friendly Bungalow!!!
June and her bungalow emanated an inviting warmth from the very beginning. My partner and I were looking for a peaceful getaway with our pup, and we were thrilled to see such a beautiful, affordable, pet friendly option by the water. I then saw that it was just 15mins from my grandmother in Waterford, so we would be able to visit with her, too! We exchanged friendly messages right after booking, and I immediately felt confident and comfortable with our decision to stay at her place. June was incredibly thoughtful and seemed to think of everything! She sent a message earlier in the week ahead of the booking to let us know she was preparing for our stay and to share excitement on the beautiful forecast. She was flexible and communicative on check in/check out times, and wished us well throughout her stay. We felt truly at home upon arrival. You can tell this bungalow has been loved and cared for, and that many good times have been shared. Very positive and serene energy. 🌅♥️🐾
Quick stats about vacation rentals in Windsor
Total rentals
60 properties
Total number of reviews
2.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Frequently Asked Questions
Do house rentals in Windsor have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Windsor. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Windsor?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with free parking, over 30 homes with air conditioning, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Windsor have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Windsor?
Windsor has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Windsor have wifi?
Absolutely! We offer over 40 house rentals with wifi in Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 40 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Windsor?
Four-legged friends are welcome in Windsor. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Windsor have free parking?
Absolutely! We offer over 30 house rentals with free parking in Windsor. Enjoy a tailored experience with all the comforts you desire.
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- Yale University
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- Clinton Town Beach
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- Six Flags New England
- Taconic State Park
- Douglas State Forest
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