Vacation rentals in Sturbridge

4.96 out of 5 average rating, 404 reviews

A colorful treehouse stands elevated among the trees, featuring a wooden deck with railings. The exterior showcases a playful combination of purple, yellow, and red, with multiple windows inviting natural light. The surrounding foliage adds to the charming, secluded atmosphere.

Treehouse in Thompson

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.

4.99 out of 5 average rating, 221 reviews

A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.

Cottage in Petersham

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

4.97 out of 5 average rating, 160 reviews

The sun sets over the calm waters of Cedar Lake, casting a golden glow across the surface. Fluffy clouds are visible in the sky, reflecting the warm colors of the sunset. A serene atmosphere is created by the natural surroundings.

Cottage in Sturbridge

Cedar Sunrise

Welcome to Cedar Lake. Come enjoy the lake and all it has to offer while staying in this cottage at the waters edge. This home may be small, but it offers a full kitchen with microwave, gas stove, Keurig and full size refrigerator. Open concept living, dining and kitchen. One bedroom with queen size bed, an open loft with a twin size bunk bed with trundle and a pullout couch in the living room. Full size bathroom with tub, washer & dryer on site. Enjoy grilling on the deck and soaking up the sun

4.93 out of 5 average rating, 431 reviews

A spacious deck overlooking Lake Bungee features comfortable seating arrangements, including wicker chairs and a swing. Colorful flower pots add vibrancy, while an umbrella provides shade. The peaceful waterfront setting is enhanced by natural surroundings and clear blue skies.

Apartment in Woodstock

“Tranquillity on the Lake ” Woodstock Valley, CT.

NEW WINTER WEEKLY DISCOUNTS Fall is here with crisp air, a treasure of rich colors embrace the trees. Enjoy your own private direct waterfront with 1400 sq ft . Queen bed in Master. Queen sofa in living area,Propane fireplace,full stove, full refrigerator, microwave. Enjoy your own deck, propane fire pit, gaze at the stars.Propane BBQ. Stroll around both lakes,catch bird sightings,nature’s delight . Many local dining & wineries. Each season paints its own stunning beauty Experience Tranquility !

4.94 out of 5 average rating, 281 reviews

A charming two-story house is nestled by the water, featuring a wraparound deck adorned with seating. The landscaped yard includes rocky pathways and a small gathering area with Adirondack chairs, inviting moments of relaxation by the water's edge.

Home in Sturbridge

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

5 out of 5 average rating, 210 reviews

The exterior of a rustic wooden house is surrounded by lush greenery and trees. A small fenced area is visible near the entrance, where a welcoming front door can be seen. The building features windows and a gabled roof, set in a tranquil natural environment.

Farm stay in Thompson

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.

4.96 out of 5 average rating, 169 reviews

The lakefront house is shown from the water's edge, featuring a grassy yard that leads to a private dock. Kayaks and a paddleboard rest along the shore, framed by trees and a clear sky. The serene water reflects the surrounding nature.

Home in Sturbridge

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!

4.88 out of 5 average rating, 225 reviews

A warm living area features a comfortable sofa adorned with patterned cushions, complemented by a cozy armchair. A wooden coffee table sits in the center, surrounded by rustic decor. The open space leads to a kitchen area, with natural light filtering through window treatments.

Bungalow in Wales

Cozy Woodland Bungalow

Unwind and relax at our rustic and cozy woodland bungalow while visiting Central/western Mass. Located on a dead end paved road surrounded by acres of woods, native plants and farm land, birds and wildlife. The perfect place to sip your coffee on the porch listening to birds. Internet access is available, as is a DVD player. Close to restaurants, microbreweries, and Old Sturbridge Village. Easy access to Route 84 or Route 19, six miles from Brimfield and eight miles from Sturbridge.

4.95 out of 5 average rating, 127 reviews

An inviting open suite features exposed wooden beams and warm, natural light. A spacious bed is positioned against a wall, framed by a colorful artwork. Comfortable seating is provided with a gray armchair nearby, complemented by bright yellow curtains covering a window.

Apartment in Sturbridge

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!

4.98 out of 5 average rating, 186 reviews

A bright living space features a spacious bed with light bedding and a cozy couch. A high-top dining table with teal chairs provides a dining area. The kitchen, equipped with essential appliances, is visible in the background. Natural light enters through a large window.

Apartment in Brimfield

Quiet & Cozy Main Street Retreat

Skip the traffic on the way to popular seasonal tourist destination, the Brimfield Flea Market, by staying here the night prior to your visit! Or, complement an off-season stay with an abundance of hiking trails, antique shops, lakes, farms, and even a winery just a 5 minute walk from your doorstep. Enjoy the ease of a convenience store, gas station, package store, and post office across the way, combined with the peace and quiet of this private suite tucked behind the main house.

4.93 out of 5 average rating, 392 reviews

A inviting living area showcases a light gray couch and a blue accent chair, complemented by a decorative coffee table. A patterned area rug anchors the space, while a fireplace is adorned with seasonal decor and small evergreen trees, creating a cozy atmosphere.

Home in Southbridge

Charming Cape--Kid & Dog Friendly 🐾

Old style cape, newly renovated. Lots of vintage charm with new upgrades. Beautiful, 3 bedroom, 1.5 bath & full kitchen. Kitchen is fully stocked with duel kuereg and drip coffee pot & Ninja blender. Beautiful touches throughout to make your stay cozy. EXTRAS INCLUDE : 24-HOUR CHECK-IN / keyless entry FREE COFFEE HIGH SPEED WI-FI Pack N Play Glider for nursing/feeding moms! SMART TVs in 3 bedrooms Enjoy a cute stay in quiet neighborhood, 7 minutes from Sturbridge exit (84).

4.99 out of 5 average rating, 211 reviews

The exterior of a red, two-story building is surrounded by a well-maintained lawn featuring trees and landscaped flower beds. A large window above the entrance and additional windows enhance the farmhouse aesthetic. Cloudy skies and natural light create a serene atmosphere.

Farm stay in Woodstock

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.

Popular amenities for Sturbridge vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Sturbridge boutique hotels

Hotel room in Hope Valley

A bright room features a spacious bed with a patterned coverlet. A small round table sits nearby, accompanied by a chair. Natural light fills the space through double doors that lead to a balcony. A fireplace and a TV are mounted on the wall.

4.68 out of 5 average rating, 60 reviews

Riverfront on The Wood River

A king size bed is framed by a decorative metal canopy, adorned with a colorful, patterned blanket and pillows. A plush stool and a vibrant patterned chair are placed nearby, adding warmth. Soft lighting is provided by matching lamps on either side.

Hotel room in Glastonbury

4.85 out of 5 average rating, 26 reviews

Private room + bath w/ balcony in a historic area

5 out of 5 average rating, 48 reviews

A cozy room features a queen-sized bed adorned with a patterned blue and gold coverlet, complemented by an array of framed artwork on the walls. A dark leather sofa sits adjacent to the bed, while a small round table rests on a warm wood floor, creating a welcoming atmosphere.

Hotel room in Worcester

JD Hotel “Blue Lagoon”

A cozy hotel room features two queen beds adorned with soft white linens and decorative pillows. A nightstand with a small plant and a magazine is positioned between the beds. A stylish wall lamp provides warm lighting against the textured wooden wall.

Hotel room in Newport

Waterfront Stay at Scenic Newport Resort, 2 Units

4.82 out of 5 average rating, 96 reviews

A cozy sleeping area features a spacious bed with a floral-patterned coverlet. There are two bedside tables, each topped with lamps. The room is flanked by windows dressed with plaid curtains, while framed artwork adorns the walls, adding a welcoming touch.

Hotel room in Cummington

Singing Bridge Harmony Room

Hotel room in Richmond

New place to stay

Access to Unmatched Amenities | Adults Exclusive

4.9 out of 5 average rating, 68 reviews

A magazine cover titled 'American-Made Luxury' is displayed, featuring a stylish room with a desk and chair. The adjoining page includes an artistic layout with sketches and design elements related to Dye House, offering glimpses into hospitality design. The overall aesthetic conveys modern elegance.

Hotel room in Olneyville

Twill - A Comfortable Queen Bed Ste at Dye House

A cozy living room area features large windows surrounded by rich wooden frames, allowing natural light to illuminate the space. A small table holds a vase of fresh flowers, enhancing the inviting atmosphere. Comfortable seating arrangements are positioned nearby.

Hotel room in Barkhamsted

Legends BNB Lodge Room 4 $109

Other great vacation rentals in Sturbridge

5 out of 5 average rating, 16 reviews

A spacious luxury home is nestled amid lush greenery, featuring a well-manicured lawn with various plants and shrubs. Stone accents on the exterior and a chimney add character, while large windows reflect the surrounding landscape. A curved pathway leads to the entrance.

Home in Spencer

Luxury Tuscan Themed Getaway

5 out of 5 average rating, 16 reviews

Lounge chairs in vibrant colors are arranged next to the tranquil lake, framed by colorful autumn foliage. The calm water reflects the tree-lined hills, creating a peaceful setting. A dock extends into the water, inviting relaxation and leisure activities.

Home in Holland

Private Lakefront Home with Beach

Guest suite in Southbridge

A welcoming outdoor space features a fire pit area and a set of turquoise chairs around a small table. A stone pathway leads to the entrance, illuminated by soft lighting along the grass, with a stairway leading to the second-floor suite.

4.91 out of 5 average rating, 22 reviews

Charming Dream Getaway Suite

4.83 out of 5 average rating, 12 reviews

A welcoming porch area features wooden flooring and a railing. Two stools are positioned beside potted plants adorned with small flags. A chair with blue and white stripes complements colorful flowers, while a watering can sits nearby, enhancing the outdoor ambiance.

Apartment in Woodstock

Woodstock Studio

4.89 out of 5 average rating, 54 reviews

A charming red exterior presents a two-story structure with a neatly landscaped entrance. The ground level features two garage doors, while the upper level displays large windows and a welcoming front door adorned with a seasonal wreath. Surrounding greenery contributes to the natural setting.

Apartment in Woodstock

Woodstock Red Barn | Private Apt in Idyllic Town

4.86 out of 5 average rating, 58 reviews

A charming bedroom is framed by patterned curtains, featuring a decorative bed with a unique painted headboard. Two bedside lamps provide soft illumination. Light-colored walls enhance the airy feel, while a rug adds warmth to the wooden flooring.

Guesthouse in Spencer

Nantucket Cottage

5 out of 5 average rating, 45 reviews

The lakeside retreat presents a spacious outdoor area with well-maintained greenery and seating options. A charming deck with comfortable seating overlooks the water, while several tall trees provide shade. Nearby, a small boat dock can be seen, enhancing the lakeside ambiance.

Home in Sturbridge

Lake House in Sturbridge w/All the Views!