Family-friendly vacation rentals in Windsor

Find and book unique family-friendly homes on Airbnb

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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Top guest favorite
A bright bedroom features a queen size bed with light linens and decorative pillows. A small desk and chair are positioned beside the bed. A closet offers hanging space, and a floral artwork adorns the wall, adding a touch of color to the space.
Guest suite in Vernon
4.98 out of 5 average rating, 204 reviews

Laura's Loft and Gallery, private suite

Unique and roomy space with private entrance, two bedrooms, full bath with tub shower, and plenty of room to relax. Kitchen space has mini fridge, microwave, toaster oven, hot plate, and crock pot. Pleasant living area opening to 2nd floor deck. WiFi with Ethernet also, great remote work space. Quiet and private, only common area shared with us is first floor entry into breezeway. Free parking on premises. Full coffee setup for your breakfast included, and homemade scones in seasonal flavors.

Superhost
A well-appointed sleeping area features a spacious bed with crisp white linens and decorative pillows. Two comfortable chairs are positioned around a circular table, complemented by a potted plant and a cozy blanket draped over one chair. Large windows allow natural light to fill the room.
Apartment in Downtown Hartford
4.89 out of 5 average rating, 207 reviews

Executive Stay Downtown Hartford

Enjoy a perfect upscale and stylish experience at this centrally located stay in downtown Hartford. With beautiful views of downtown Hartford overlooking our central park known as "The Green", this unit has everything you need (+blackout curtains) . This is Immediately across the street from the XL Center, home of our UCONN HUSKIES, and a short, quick walk from the executive buildings. Come enjoy an amazing stay at one of the premier locations in the city. (Also includes easy parking access.)

Superhost
A bright workspace features a wooden desk with a black chair, positioned against a light-colored wall. Two framed botanical prints are displayed above the desk, complemented by a standing lamp. A mirror reflects the scene, while a potted plant adds a touch of greenery.
Apartment in Windsor Locks
4.85 out of 5 average rating, 177 reviews

Apt near Big E, Six Flags, Bradley airport

Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

Guest favorite
A cozy living room features a stone fireplace surrounded by purple walls. A wooden table sits at the center, adorned with a decorative bowl. A comfortable sofa and a wooden chair are positioned near the fireplace, complementing the warm ambiance.
Cottage in Windsor
4.9 out of 5 average rating, 196 reviews

In-law apartment in Farmington River Cottage

If you are craving a getaway with a special someone, this space is meticulously clean and an opportunity to practice social distancing while relaxing and enjoying the Farmington River. Only 15 minutes from Bradley airport, 5 minutes from the train and I91. Nature, dining, all within a comfortable drive. You get it all here! Private space with its own entrance, one bedroom and newly updated bathroom, a cozy living room with fireplace in a Garden Level Unit. Off street parking available.

Top guest favorite
An entryway features a wooden sideboard with a marble top and a wine rack below. Metal vases with decorative grasses are placed on top, accompanied by a lamp providing soft illumination. A coat rack stands nearby, and a textured rug lays on the floor.
Place to stay in Coventry
4.99 out of 5 average rating, 121 reviews

Get Away Rock Farm Suite UConn Best Rated Clean

The Get Away Studio Suite on Rock Farm” is a quiet, safe, airy 600 sf open floor plan with 9ft ceilings. Peaceful secluded country setting 600ft in woods. Enjoy a comfy king bed, twin bed, kitchen, dining, living area & full bath. All Sundries & amenities. DIY breakfast! Near malls, groceries, lakes, 13 min UCONN, 20 min Hartford, trails & parks only mins away. WE ARE 5 ⭐️ RATED CLEAN with excellent hospitality. See The Hide Away https://www.airbnb.com/h/atrockfarm

Guest favorite
The inviting living area features a door leading to the patio, allowing natural light to fill the space. A wall clock and TV are positioned on gray walls, complemented by a coffee table and cozy seating. Views of the green outdoors can be seen through the windows.
Guest suite in Bloomfield
4.98 out of 5 average rating, 124 reviews

Guest Suite with Private Entrance & View

Relax at our Guest Suite Apartment with a private walk-out entrance on the lower level of our home. Nestled at the end of a quiet neighborhood road our space is just 15 minutes from Bradley Airport & less than an 8-mile drive from Hartford. Have fun with the local bike path, hiking, wineries, and breweries. Afterward, kick up your feet on the queen mattress or unwind on the patio in our peaceful backyard often visited by deer.

Top guest favorite
A round wooden table is set with woven placemats, featuring a white cup filled with frothy coffee. A tall vase with a vibrant sunflower adds a touch of color, while a small tray with assorted snacks is visible in the background.
Apartment in New Britain
4.96 out of 5 average rating, 223 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Top guest favorite
The exterior of a historic brick house is showcased, featuring a rounded turret and a welcoming front porch. Lush greenery and colorful flower beds surround the entry stairs, which lead to the front door. A small garden area adds to the inviting atmosphere of the home.
Loft in Frog Hollow
4.99 out of 5 average rating, 737 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.

Guest favorite
A brick patio area is seen with two rocking chairs positioned beside vibrant orange and yellow flower pots. A welcoming wreath adorns the double doors, and a pumpkin is placed on the ground, enhancing the seasonal decor.
Guest suite in East Granby
4.85 out of 5 average rating, 382 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

Top guest favorite
A bright living area features a dark sofa with multiple cushions, flanked by two patterned chairs. A wooden coffee table is positioned in the center, and a laptop is placed on it. Natural light enters through the two windows, adorned with dark curtains.
Apartment in Enfield
4.99 out of 5 average rating, 277 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

Guest favorite
The open living space features a kitchen island with a granite countertop and wooden cabinetry. A dining set with high chairs is positioned nearby. A comfortable blue sofa and a television stand are visible in the living area, complemented by hardwood flooring throughout.
Apartment in Manchester
4.96 out of 5 average rating, 106 reviews

Cozy 1 bedroom clean and quiet

Experience the charm of Manchester CT in this fully furnished 1 bedroom apartment! Available now. Pet-friendly, with laundry facilities conveniently located within the unit. Enjoy easy access to highways from this centrally located apartment while being just minutes away from quaint downtown area amenities.

Guest favorite
A red barn-style building with large windows is shown against a clear blue sky. The surrounding area is covered with snow, highlighting the building's architecture. Shadows from nearby trees fall gently on the ground, creating a peaceful winter scene.
Guest suite in Windsor
4.86 out of 5 average rating, 153 reviews

Rustic Loft Apartment

Cozy studio apartment, minutes from the center of Windsor. Easy access to I-91, grocery stores and Target minutes away. Plenty of off-street parking, private entrance. Laundromat available down the street. The second bedroom is the loft area above the kitchen. The apartment is above a wood working shop.

Popular amenities for Windsor family-friendly rentals

When is the best time to visit Windsor?

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Avg. priceG$36,586 GYDG$31,359 GYDG$31,359 GYDG$31,359 GYDG$35,332 GYDG$32,196 GYDG$29,687 GYDG$29,478 GYDG$31,359 GYDG$32,196 GYDG$34,077 GYDG$31,359 GYD
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Quick stats about vacation rentals that are family-friendly in Windsor

  • Total vacation rentals

    Explore 20 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at G$12,544 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,110 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Windsor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor rentals

  • 4.8 Average rating

    Windsor stays are highly rated by guests—averaging 4.8 out of 5!