
Family-friendly vacation rentals in Roxbury
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Roxbury
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub
Step into the stylish and peaceful 3BR 2.5BA cabin in a historic Merryall District close to shops, lakes, hiking trails, farms, and downtown New Milford and Kent. Explore the picturesque area and the exciting attractions, or lounge by the fireplace or the fire pit in the magical yard. ✔ 3 Comfortable Bedrooms ✔ Living Room & Sunroom ✔ Wood Burning Hot Tub ✔ Chef's Kitchen ✔ Office/Library ✔ Books, Vinyls & Games ✔ Porch, Yard & Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry See more below!

Get Away to "Hygge" Tiny House on 75 Private Acres
Escape to 75 acres of secluded, private land and lounge in this "hyggelig" tiny house. The house has everything you need, from heat and A/c, strong wifi, TV with streaming (sign in to Netflix, HBO, etc), full working kitchen (gas stove, oven, microwave), shower and bathroom. This tiny house has an incredible amount of light coming in from the very large windows throughout. Outdoor amenities include wood patio, propane bbq grill, dining table/chairs, fire pit. Lawn games available on request.

Cozy Cottage |Quintessential CT | Pet Friendly
Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

The Cottage on Babbling Brook
A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

The Farmhouse
Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Peaceful apartment on 3.5 acres w/ Artist studio.
Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Sticks and Stones Farm - The Solar Cabin
Sticks and Stones Farm offers a rustic glamping experience! When you stay with us you'll get the adventure and fun of camping (no electricity, outdoor showers etc.) while still getting to lay your head on a soft pillow in a bed. You can treat your stay here as a chance to go inward or enjoy interacting with the different programs and events going on! If you want to be up to date on events or ask about weekday checkins you can message us directly.

Cozy Apartment with Water View of Brook
Lower Level Beautiful Space: Well kept with an amazing view of a Beautiful Brook that Runs through the Backyard. It is a small cottage style home and you will have the best views of the Brook. You will also hear and see the Brook from the Bedroom, Kitchenette and Patio. Depending on the season it will Vary. If you have 2 Cars please make sure you let me know so I can accommodate.

Beautiful Brook-side Log Cabin on 3 Private Acres
Fall asleep to the sound of the rushing brook in this beautifully restored log home. The cabin sits in the middle of three wooded acres overlooking Catlin Brook as it cascades through the gorge below. It seems like wilderness, yet all the amenities of Harwinton are just a few minutes away.

Light and airy, pet friendly rental in Newtown
Enjoy a light and airy space in a quiet and serene suburban setting, yet a 5 minute drive from shopping and restaurants . A wooded culdesac is within steps to walk your dog or just go for a stroll. Many nearby attractions whether Winter, Spring, Summer or Fall!

The Getaway-HOST & Co.
Come and unwind within the idyllic charm of Litchfield County. Relax in the spa or lounge by the heated pool and to take it all in. We are located on a quiet country road just 2 miles out of the center of Litchfield and 1.5 miles from the Borough of Bantam.
Popular amenities for Roxbury family-friendly rentals
Family-friendly home rentals with a hot tub

Lakefront Bungalow Bliss | Serene 2BR Retreat

Breathtaking home with unforgettable views & pool!

Foxglove Farm

40-Foot Container Cabin in the Catskills

Relaxing secluded stay with loving social animals.

(°) The Wandering Peacock (°)

Luxe Bolton Lake

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room
Family- and pet-friendly home rentals

Geodesic Dome in the Wooods

County Seat Colonial/Walk to Town-HOST&Co

Private and Serene home close to I-84 and shopping

The Waterfall House

Private Woodland Sanctuary—3 mins to a lake beach!

Huge eclectic space w/ private pool. 1.5hr to city

Blackberry Cottage

Rustic Pond Cabin: Nature, Stars & Serenity
Family-friendly home rentals with a pool

Escape to a Restored New England Antique Milk Barn

Entire Home (private pool), Event Friendly

Garden Level Suite with Beautiful Pool

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

E and T Getaway LLC

Charming apartment with breathtaking view!

4Br Mountain Brook House on 130 acres w/ trails

Peaceful Light-Filled Guesthouse salt pool/sauna
Destinations to explore
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- Yale University
- Six Flags New England
- Thunder Ridge Ski Area
- Fairfield Beach
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Sunken Meadow State Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Mohawk Mountain Ski Area
- Taconic State Park
- Hammonasset Beach State Park
- Bear Mountain State Park
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Storm King Art Center
- Yale University Art Gallery
- Ski Sundown
- Millbrook Vineyards & Winery
- Sherwood Island State Park
- Compo Beach
- Mount Southington Ski Area





