Family-friendly vacation rentals in Windham County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Windham County

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

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Guest favorite

Guest suite in Tolland

4.9 out of 5 average rating, 324 reviews

UCONN Hideaway

Open, light floor plan with TV and cable sleeping 4 adults 1 full bed and twin bed w/ pull out sofa. Private access and parking. Full kitchen and full bathroom. Quiet rural area with quick access to Interstate 84 and Hartford. There are parks and tennis courts and walking trails very close to Our UCONN Hideaway. Later in the year you will see the beautiful flowers and vegetables that fill the yard. We are organic landscapers and use no harmful chemicals or practices in our business,home or yard.

Guest favorite

Farm stay in Southbridge

4.89 out of 5 average rating, 316 reviews

Scandanavian Wigwam with Sauna and Forest Baths

Deep sleeps await in our off grid forest Wigam. With everything you need, and nothing you do not, this exceptional retreat boasts a Danish Morso wood stove, fire pit, private forest baths, Finnish sauna, HUGE windows overlooking a wildlife trail and Peepers Owls and Coyote song. From photo shoots to wedding proposals - this is a special place to care for yourself and your family. We are on farm - but out of sight. Bring your kids, dogs, friends, guitar, or just a good book and settle in!

Guest favorite

Home in Woodstock

4.94 out of 5 average rating, 231 reviews

Cedar Ridge: House or House+Apartment

2 OPTIONS: HOUSE or HOUSE+APARTMENT In CT’s Quiet Corner: renovated 2-level house bathed in light, with nice flower beds and stunning hilltop views. Relax on its patios and in its small swimming pool, stroll along its forest paths, observe birds (including birds of prey) and other wildlife. New England's "Last Green Valley National Heritage Corridor" offers multiple attractions and is home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities.

Guest favorite

Guest suite in Worcester

4.88 out of 5 average rating, 418 reviews

Private Suite with separate entrance in Worcester

This private suite allows a maximum of two pets per reservation for $50 per a pet. Our guests privacy starts from check in to check out with private entrance gate. The living room has a mini library for guests, 55" TV with Internet streaming channels and fully subscribed YouTubeTv. The suite also has a mini kitchen with a refrigerator, a freezer, a microwave, air fryer, omelet egg maker and coffee maker. It also has fully stocked linen closet and electric pump air mattress if necessary.

Guest favorite

Cabin in Voluntown

4.95 out of 5 average rating, 706 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

Vinola is the "Cabin in the Woods" you've been looking for! Enjoy an idyllic escape from the city year-round. Activities include swimming, fishing, hiking, kayaking or just a cozy snooze with a book on the couch. Top off your stay by trying our traditional wood-fired Finnish sauna. Relax tired muscles and rejuvenate the soul. Private beach and lake access on Beach Pond just 335 feet from the cabin. Check our photos and reviews! Our guests consistently remark that one night isn't enough.

Guest favorite

Guesthouse in Sprague

4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

Rustic cottage on on Little River, a lovely trout stream that swishes around rocks. Great place for kids to play! Lake across the street. Canoe. Woods all around. Very quiet except for hush of river. Nice deck extends almost to the river. Charcoal grill. In all ways cozy and pleasant. Nice for couples, writers, artists, travelers, families, and pets—a place for quiet, peaceful people. About the lake: There's no beach. Access is just a narrow path down to the water.

Guest favorite

Rental unit in Brooklyn

4.85 out of 5 average rating, 217 reviews

8 Bedroom, 4 full bath residence with 40' pool

Fully appointed guest suite in renovated 150-year old post & beam barn. Exposed original wooden posts, beams and pegs. Three floors. 8 bedrooms (1 full and 7 queen beds) with A/C. 2 bedrooms have attached bathroom and 4 have cathedral ceiling.. 2 living rooms, 4 full bathrooms, full kitchen, separate kitchenette, large dining area and solarium. 4 stone-walled acres. Shaded 40 ft pool with screen house and outdoor cooking and dining area..

Guest favorite

Guest suite in Brooklyn

4.93 out of 5 average rating, 173 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Guest favorite

Guest suite in Mansfield

4.96 out of 5 average rating, 201 reviews

Cozy private apt 8 mins from UCONN - solar powered

Relax & unwind in this amply sized private studio suite, complete with large seating/tv area & study/desk space. Space comes w/ 2 beds (1 queen, 1 full sized pull out futon couch) a full private bath, mini-fridge, cooktop, microwave, dishware, & utensils. Beautiful rural wooded area with numerous hiking trails nearby. Longer term rentals may be considered starting from Summer of 2025

Guest favorite

Home in Brimfield

4.94 out of 5 average rating, 158 reviews

Brimfield Lakeside Home Away from Home

Renovated Brimfield Lakeside Home: minutes to downtown Brimfield & Sturbridge offers two bedrooms plus additional upstairs loft sleeping area, one bath & sleeps six. We are a year round property located in a quiet cove on beautiful Little Alum Pond in Brimfield, Massachusetts. Extremely tranquil setting, yet plenty of great restaurants and shopping are just minutes away.

Guest favorite

Treehouse in Willington

4.9 out of 5 average rating, 380 reviews

Treehouse | Countryside | Farm Animals | Fire Pit

Guest favorite

Cabin in North Stonington

4.96 out of 5 average rating, 186 reviews

Snuggle with a glass of wine in front of the fire

Come to the woods of Southeastern Connecticut and enjoy some solitude and connection in the woods while wrapped in our flannel LL Bean bathrobes. Snuggle with a glass of wine or coffee by the fire and unplug, rest, and rejuvenate with your partner or by yourself. Only fifteen minutes away from casinos, shopping or restaurants in Mystic or downtown Westerly, RI.