Family-friendly holiday rentals in Sturbridge

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Sturbridge

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Chalet in Otis

4.94 out of 5 average rating, 418 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favourite

Home in Woodstock

4.94 out of 5 average rating, 239 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.

Superhost

Cabin in Holland

4.82 out of 5 average rating, 209 reviews

4 Seasons Lake View Cabin Holland

Quirky quaint older cabin. Small, but functional spaces, natural landscaping and under the trees , well water. Other seasonal and year round cabins surround it.If you are NOT looking for a chain hotel this is a great space, it has upgrades like mini splits, but it is a cabin and is for the nature lover who enjoys the area, the lake, the quiet and proximity to Brimfield Markets, Sturbridge Village, Tree House etc . I strive to keep updating and improving, great location to explore New England

Guest favourite

Guest suite in Worcester

4.88 out of 5 average rating, 444 reviews

Private Suite with separate entrance in Worcester

The suite allows maximum of two pets per reservation for $50 per a pet. Our guests privacy starts from check in to check out with private entrance. The living room has mini library for guests, a 65 inch smart TV with high speed Internet and complimentary YouTubeTV local channels. The suite has a mini kitchen with mini refrigerator, freezer, microwave, air fryer, and coffee maker. It also has stocked cabinet utensils, cleaning supplies, linen closet and electric pump air mattress if necessary.

Top Guest favourite

Place to stay in Sherborn

4.97 out of 5 average rating, 298 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Guest favourite

Home in Sturbridge

4.96 out of 5 average rating, 169 reviews

Cedar Lake 3 Bed 3 1/2 Bath Home Sturbridge MA

Fully equipped w/open lake view living space w/gas fpl. Direct access to Lake w/private dock, (2) kayaks, decks, patio, grill & fire pit. Pvt master bed/bath and 2nd bed w/lake view/deck access. Base rate up to 5 people. $50/each add pers-night max 8 tot. 4th bed is futon in finished walkout bsmt with 3rd full bath. Min 3 night stay. Base weekday $375, Weekend $475. Premium rates seasonally/holidays. Local tax added by AirBnB. Ck-out 11 AM, Ck-in 3 PM unless arranged. Sorry no more pets.

Top Guest favourite

Home in Oakham

5 out of 5 average rating, 167 reviews

Lovely & Peaceful Waterfront Vacation Retreat

Come enjoy this unique & beautiful retreat home, set on 50 acres of wooded land, with a breath-taking view over a 2 mile long, 190-acre body of water, & no houses in sight! Wonderful in any season. Peaceful, healing haven, & great get-away spot for a romantic weekend or family vacation. Perfect for swimming, boating, fishing, hiking, & cross-country skiing--or just relaxing in a hammock, on the deck, or in a bedroom overlooking the water. Youtube Video: Fred's Place, James Crowther

Guest favourite

Barn in Holden

4.89 out of 5 average rating, 466 reviews

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Guest favourite

Guest suite in Brooklyn

4.93 out of 5 average rating, 191 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.

Top Guest favourite

Home in Brimfield

4.93 out of 5 average rating, 167 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.

Top Guest favourite

Apartment in Northampton

4.92 out of 5 average rating, 632 reviews

Sunny Peaceful Home

This is a home-away-from-home! The space includes a full kitchen, laundry, wireless Internet, a queen-size bed, and more. Located in a safe, quiet, residential neighborhood, there is a river out back for swimming and many books and toys in the apartment if you're traveling with small children. You'll also have a beautiful view of the river from the 2nd-floor back deck!

Guest favourite