
Vacation rentals in Windsor
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor vacation rentals
Other great vacation rentals in Windsor

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
The house felt like coming home. Everything you need was provided. The location is beautiful as is the surrounding area. We needed proximity to family and this was a perfect spot. All the amenities in the home were available and perfect for a weeklong stay. Thank you for a great stay!

Beautiful Cabin in Cornwall CT.
Henry's beautiful home and yard provided the perfect getaway for 5 friends who try to get together at least once a year, coming from 3 different states. The large rooms, clean/fresh bed linens and towels, two full bathrooms and spacious living room adjacent to the kitchen gave us jus t the right setting in which to enjoy each other's company. Breakfast at the kitchen table overlooking the backyard was bright and sunny first thing in the morning. We especially liked the backyard patio, which gets sun all day long. After a cold rainy start to our stay, we were able to enjoy a warm afternoon on the patio - sunshine, blue skies, birds, budding trees and the soothing sound of the water fountain and small pond . We found great restaurants in both Kent and in Litchfield. As an avid gardener, I can just picture Henry's beautiful landscaping when all is in bloom later in the season. Very comfortable place to hang out! We wouldn't hesitate to give others a recommendation for Henry's home.

Rural Litchfield County Apartment Goshen CT
Wonderful stay and reasonably priced. We were attending a concert at the Warner Theater in the area so we made a weekend of it. There was a Vineyard and a farm that made their own chocolate nearby that we visited during our stay. The scenery was countryside side farm with Mohawk mountain nearby for a view. The accommodations were clean and comfortable and the host Pauline was available for any concerns.

"Red House on the Knoll" at Indian Cove
My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!

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. 🌅♥️🐾

Private apartment in residential home by the beach
Warm cozy and welcoming. Felt like home! We had a wonderful relaxing weekend and felt right at home. And we definitely look forward to coming back! Mercy was a wonderful host and very helpful and accommodating! Thank you again for the hospitality!

Great Hammcock Getaway, Nearby beaches, Hot tub
What a beautiful place and conveniently located. The house was wonderful decorated, was very comfortable and definitely was a relaxing place to get away. Irina was a wonderful host and the home had many wonderful amenities to offer.
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.
Destinations to explore
- The Hamptons Vacation rentals
- Hudson Valley Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Cape Cod Vacation rentals
- Pocono Mountains Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Yale University
- Foxwoods Resort Casino
- Catamount Mountain Ski Resort
- Ocean Beach Park
- Six Flags New England
- Quotonset Beach
- Giants Neck Beach
- Woodmont Beach
- TPC River Highlands
- Clinton Town Beach
- Taconic State Park
- Attawan Beach
- Shennecossett Beach
- Anchor Beach
- Clinton Beach
- Groton Long Point Main Beach
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Fort Trumbull Beach
- Burwells Beach
- Sleeping Giant State Park
- Bayview Beach
- Barbara Pine Memorial Beach
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes