Vacation rentals in Windsor

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Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

Price Chopper15 locals recommend
Revolutions Bowling and Lounge7 locals recommend
University of Hartford5 locals recommend
Tunxis Grill & Pizzeria5 locals recommend
Thomas Hooker Brewery5 locals recommend
The Children's Museum5 locals recommend

Other great vacation rentals in Windsor

Top guest favorite
A wooden deck is visible, offering seating with blue rocking chairs. Lush greenery and a serene lake are seen in the background under a partially cloudy sky. The space invites relaxation and enjoyment of the natural surroundings.
Home in Granby
5 out of 5 average rating, 7 reviews

Lake house retreat Granby CT

DianeRating, 5 stars1 week ago
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!!!
Top guest favorite
A serene view of a private lake is captured during twilight, with gentle colors reflected on the water's surface. A stone bench is visible in the foreground, accompanied by a potted plant, and lush green grass leads to the lake's edge.
Home in Andover
4.98 out of 5 average rating, 56 reviews

Spacious Classic Lakefront Home with jet tub

JeffreyRating, 5 stars3 months ago
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!
Top guest favorite
Cabin in Cornwall
5 out of 5 average rating, 48 reviews

Beautiful Cabin in Cornwall CT.

JanRating, 5 stars2 weeks ago
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.
A cozy studio space features a door leading to a private outdoor area, with natural light streaming in through a skylight. A neutral-toned sofa is positioned near a television, accompanied by lamps that provide soft illumination, enhancing the welcoming atmosphere.
Guest suite in Goshen
4.73 out of 5 average rating, 249 reviews

Rural Litchfield County Apartment Goshen CT

KennethRating, 5 stars2 weeks ago
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.
Top guest favorite
The inviting living area is characterized by high beam ceilings and a stone fireplace. A stylish coffee table with a cowhide design sits at the center, surrounded by colorful seating. A flat-screen television is positioned for easy viewing, with natural light streaming from large windows.
Cottage in Guilford
4.99 out of 5 average rating, 136 reviews

"Red House on the Knoll" at Indian Cove

MaryRating, 5 stars2 weeks ago
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!
Top guest favorite
A wooden dock extends over the calm water, featuring two Adirondack chairs positioned to enjoy the scenic views. A ladder is attached to the dock, providing access to the water. Lush greenery surrounds the area, contributing to a peaceful ambiance.
Bungalow in Old Lyme
4.94 out of 5 average rating, 306 reviews

Pet Friendly Bungalow!!!

BrittanyRating, 5 stars1 week ago
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. 🌅♥️🐾
A serene outdoor space is featured, with a shaded pergola providing seating beneath. Two hammocks are suspended, surrounded by lush greenery. A circular stone patio includes a set of metal chairs and a small table, complemented by blooming flowers in the foreground.
Home in West Haven
4.75 out of 5 average rating, 119 reviews

Private apartment in residential home by the beach

StephenRating, 5 stars2 weeks ago
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!
Top guest favorite
Home in Old Saybrook
5 out of 5 average rating, 49 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

DavidRating, 5 stars1 month ago
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.

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