Family-friendly vacation rentals in Windsor

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Top-rated family-friendly rentals in Windsor

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Middletown

4.94 out of 5 average rating, 706 reviews

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

Mar 21 – 28

G$25,297 GYD per night

Guest favorite

Home in Granby

4.95 out of 5 average rating, 220 reviews

FULLY stocked Ranch Home, * Gardens* Gameroom

Clean refreshing three-bedroom , one floor living, centrally located, walk to town for fantastic dining ! Mexican, Sushi and Thai, Mediterranean, Italian, Continental, and Vegan ! 8 minutes to rt 91 and Bradley, minutes to Mass line! Downstairs living space with a gameroom and comfortable seating, and extra sofa bed and airbeds, if needed. Other than clothes, you will need nothing else...I provide everything from razors to coffee , tea and a HUGE snack basket ! Even have a heating pad .

Aug 31 – Sep 7

G$36,275 GYD per night

Guest favorite

Cabin in Cummington

4.98 out of 5 average rating, 162 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Sep 17 – 24

G$14,055 GYD per night

Guest favorite

Apartment in Glastonbury

4.9 out of 5 average rating, 409 reviews

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

Dec 11 – 18

G$23,818 GYD per night

Guest favorite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

May 3 – 10

G$25,030 GYD per night

Guest favorite

Home in Feeding Hills

4.89 out of 5 average rating, 884 reviews

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, good for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

Sep 8 – 15

G$25,251 GYD per night

Guest favorite

Home in New Hartford

4.89 out of 5 average rating, 133 reviews

Modern Farmhouse

This is a quaint, sun-filled farmhouse in the Farmington valley of Connecticut. Convenient to great antique shopping, Ski Sundown, farm stands, Farmington river inner-tubing and biking trails, kayak and canoe rentals, the sweet towns of Collinsville and New Hartford, and a 30 minute straight shot to Hartford itself. The house is also convenient to Torrington, Simsbury, Avon, Winsted, and a beautiful drive to Hartford-Bradley International Airport.

Jun 7 – 14

G$31,111 GYD per night

Guest favorite

Loft in Hartford

4.98 out of 5 average rating, 534 reviews

Loft - Queen Anne Row House in a historic district

Hosted by Judy and Greg, our home is close to art, culture, live theater, and restaurants. Our home is also close to major insurance companies, the state capitol and state of Connecticut offices. You’ll love the cozy 3rd floor loft. We also offer off street parking. Garage space is also available as an option. Our home is a perfect destination for couples, solo adventurers, and business travelers.

Nov 15 – 22

G$23,310 GYD per night

Superhost

Guesthouse in Granby

4.9 out of 5 average rating, 192 reviews

The Loft @ Lost Acres ~ A Peaceful Rural Escape!

The Loft @ Lost Acres Vineyard is a wonderfully private, rural getaway! This bright and comfortable space is located on the upper floor of a Lost Acres Vineyard barn. Originally intended for the caretaker, the owners are now offering it to the public to enjoy the beauty of the vines & the stunning rural scenery of North Granby. Oh, and stop by the tasting barn, the wine is AMAZING!

Nov 9 – 16

G$31,146 GYD per night

Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 340 reviews

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

Dec 12 – 19

G$20,508 GYD per night

Guest favorite

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

Jun 2 – 9

G$31,276 GYD per night

Guest favorite

Apartment in Portland

4.88 out of 5 average rating, 461 reviews

SUNNY PRIVATE 1 BEDROOM APARTMENT

Feel right at home in this modern meets traditional 1 bedroom apartment. Features a full kitchen, living room and reading nook/office . A short 5-10 minute drive to Wesleyan University, Downtown Middletown, Middlesex Hospital and Saint Clements Castle.

Jul 9 – 16

G$19,360 GYD per night