Family-friendly vacation rentals in Sturbridge

“Tranquillity on the Lake ” Woodstock Valley, CT.

WINTER WEEKLY & MONTHLY DISCOUNTS.The beauty of the serene winter awaits you. Featuring your own private direct waterfront with 1400 sq ft.of indoor living space . Queen bed in Master Suite. Queen sofa in living area,Indoor propane fireplace,full stove, full refrigerator, microwave. Enjoy your own deck, propane fire place.Sway on the swing , gaze at the stars.Stroll around the lake, see local birds. Great nearby dining,wineries,breweries . Enjoy this winter and embrace the joy of lake living !!

Lake Front Home Sleeps 6-8 on a private Peninsula!

Stunning year-round waterfront home on its own private peninsula—sleeps 6–8 with 3BR/2BA, a spacious living room with sliders to a wraparound deck, and a heated sun porch offering panoramic lake views. Nearly every window overlooks the water. Outside, enjoy a private dock, new stone patio & firepit, small beach area, kayaks, canoe, and rowboat. Perfect for families, couples, or a friends’ getaway. See walkthrough videos at on YouTube @CedarLakeCottage Summer: 4-night min | Holidays: 3-night min

Rustic Farmette Studio w/yearround Hot Tub

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

Wizard's Roost at Underhill Hollow

Have you ever slept on a floating bed, levitated a planet with a wand, played wizard's chess, spoken with a bird house, watched a heron hunt, crawled through a halfling door or fed goats by hand? At the Wizard's Roost you can do this plus much more. Animate a Pegasus, sample a Spider Crisp, go on a treasure hunt or find fairy houses all while staying in an A-C cabin with a full private bath. Built on the mythical site of Yarvard Hale School of Magic, this get away places you inside a dream.

LAKE Retreat! Lakefront Home with Amazing Views!

Beautiful lakefront house with great views. Perfect for a relaxing family vacation. 4 Bedrooms, 3.5 baths sleeps 10 comfortably. Paddle-board, kayak, propane grill, fire pit, & corn hole make for awesome lakefront memories! Game room features bubble boy hockey, board games, & puzzles for rainy day fun! Sturbridge is known for it's locally owned restaurants, breweries, & wedding venues. Get away from it all, but still be close driving proximity to Boston, Worcester, Springfield MA, & CT!

Craig's Cove

Craig's Cove is a two-room apartment (in my finished basement) with a farmhouse industrial motif and is in close proximity to Sturbridge, wineries, micro-brews such as Lost Towns Brewing, and beautiful scenery. Guests will be provided with one off-street parking space, private entry, bedroom with queen-size bed, full bathroom, TV with Netflix & Amazon Prime, free wifi, coffee, kitchenette with sink, microwave, fridge, toaster oven, hot plate (no full size stove), and patio with pergola.

Main Street Suite

Enjoy a boutique hotel experience in a historic New England town. This private, well-equipped suite is housed in a mixed use building (with a few small businesses with daytime hours) next door to a popular craft beer pub, and across the street from a hopping neighborhood Japanese restaurant. Enjoy everything you need in a home base with quick access to Old Sturbridge Village, lakes, trails, wineries, breweries, restaurants, farmers’ markets, festivals, events, antiquing, and more!

Barn suite at Southwood Alpacas

Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.

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.

Little House Inn - Brimmy - Private Home

Relax & enjoy the whimsy of our Little House. Create your own fantasy in our Pirate/Castle-themed bedroom perfect for kids of all ages. Our home is kid & pet friendly, filled with games and activities for the whole family. Enjoy our home's private backyard that includes a babbling brook & fire pit. Whip up a meal in our full kitchen then sit back & relax with the family or friends. Check out our guidebook for places to eat & sightseeing opportunities.

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.

Enjoy a Farm Stay without the Work

This 3-room one-story apartment with private entrance is attached to the main 1850 farmhouse and also has that older farm charm. Only 10 minutes to Interstate 84 and midway between New York City and Boston, this location allows for ease of access to experiences in the northeast. The property is set back from the state road (Route 89) and allows for relaxed living on a beautiful farm bordered by stone walls and wooded area behind.