Family-friendly holiday rentals in Tolland County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Tolland County

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

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Guest favourite

Treehouse in Thompson

4.96 out of 5 average rating, 399 reviews

The Tree House at Underhill Hollow

The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.

Top Guest favourite

Cottage in Vernon

4.97 out of 5 average rating, 114 reviews

Vintage Bolton Lake

Experience the nostalgia of vintage lake charm and enjoy the calming lake waters! The Vintage is nestled on the shores of picturesque Middle Bolton Lake. Relax, unplug, and savor the good life of times past. The cottage has been tastefully updated and outfitted with period furnishings to allow for vacationing in comfort and style. As our guest, you will enjoy full use of the cottage, WiFi, property, propane grill, smokeless firepit, kayaks and much more. Come enjoy vintage lakefront lifestyle.

Top Guest favourite

Guest suite in Vernon

4.98 out of 5 average rating, 193 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.

Top Guest favourite

Place to stay in Coventry

4.99 out of 5 average rating, 112 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 the comfy king bed, twin bed, kitchen, dining, living area & full bath. All Sundries & amenities. DIY breakfast on us! Near malls, shopping, lakes, 13 min UCONN, 20 min Hartford, trails & parks only mins away. WE ARE 5 ⭐️ RATED CLEAN with excellent hospitality. Need more space? See The Hide Away https://www.airbnb.com/h/atrockfarm

Guest favourite

Loft in Tolland

4.97 out of 5 average rating, 259 reviews

Cozy studio loft

Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

Top Guest favourite

Guesthouse in Portland

5 out of 5 average rating, 223 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Top Guest favourite

Home in Coventry

4.98 out of 5 average rating, 121 reviews

Cozy cottage 5 minutes from UConn

Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a warm morning coffee while enjoying the lake view from the bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

Guest favourite

Cabin in Windham

4.85 out of 5 average rating, 170 reviews

Secluded Cabin on Golden Pond

• Cozy Cabin on Golden Pond! • Fire Pit, (free wood)! • Fishing! • Kayak, Paddle Boat Canoe, Row boat! • Hiking! • Swimming! • Sand Beach! • Picnic Table, Chairs! • Grill! • WiFi! • Cooking Utensils, Service 4 six! • Air Conditioning! . Soap Stone Fire Place! . Comfy Couch, Smart T.V.! . Beds: 2 Full, 2 Twin, 1 Queen on Porch! • 14x14 Tent platform at waters edge! (Camping gear not provided) • Secluded! • Wildlife!

Top Guest favourite

Guest suite in Mansfield

4.96 out of 5 average rating, 208 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 favourite

Treehouse in Willington

4.92 out of 5 average rating, 459 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Guest favourite

Apartment in Stafford

4.94 out of 5 average rating, 157 reviews

Modern Industrial Apartment with rooftop access

* Modern industrial apartment with rooftop access. * Nestled in an old Mill Building/Artist Community. * Centrally located between Boston and NYC. * 15 mins to UConn, 20 mins to Brimfield Antique Show. * 40 mins to MGM Casino in Springfield, MA. * Walk to restaurants, boutiques, parks, and events. * On-site Yoga, Dance, Recording Studio & Vintage Shop.