Vacation rentals in Southbridge

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Top-rated vacation rentals in Southbridge

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Guest favorite

The image showcases a spacious green yard surrounding a charming gazebo. In the foreground, assorted seating arrangements invite relaxation. The background features trees in full bloom, enhancing the natural setting and providing a peaceful atmosphere.

Home in Brimfield

4.88 out of 5 average rating, 231 reviews

Little House Inn - Brimmy - Private Home

NO CLEANING FEES - NO CHORE LIST. Relax with the family at our Little House. Create your own fantasy in our Pirate/Castle-themed bedroom perfect for kids of all ages. Our home is kid and pet friendly. We provide a portable crate for pet, food bowls, a kitty litter box and large back yard for our furry guests . Enjoy our home's private backyard that includes a babbling brook & fire pit. Whip up a meal in our full kitchen then sit back and relax with the family or friends. Check out our guidebook for places to eat & sightseeing opportunities.

Top guest favorite

An open living and dining area highlights natural wood elements and modern design. A comfortable leather couch is positioned against a wall adorned with wooden decor. An inviting dining table accommodates several guests, while stainless steel appliances complement the functional kitchen space.

Home in Sturbridge

4.97 out of 5 average rating, 188 reviews

Modern Lakeview House -Chef's Kitchen, Strong Wifi

This house has clean, light, modern design, full of unique details you'll love. Like a large modern kitchen, spa bathroom w/ jacuzzi tub, deck w/ lake view. A few steps from Cedar Lake beach, tennis, playgrounds. Walk to downtown Sturbridge restaurants or cook in our stocked chef's kitchen full of gadgets. Perfect for a "stay-cation" or to work from new location. Visit local Craft Breweries (Treehouse Brewing) and natural trails. A getaway 60min to Boston, 40min to Hartford, 20min to Worcester.

Top guest favorite

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

4.97 out of 5 average rating, 156 reviews

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

Guest favorite

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

4.93 out of 5 average rating, 425 reviews

“Tranquillity on the Lake ” Woodstock Valley, CT.

Fall is almost here with crisp air, a treasure of rich colors embrace the trees. Enjoy direct waterfront & sunrises ,1400 sq ft. Queen bed in Master. Queen sofa in living area,Propane fireplace, AC, 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,a true nature’s delight . A variety of local dining & wineries. Each season paints its own stunning beauty. Relax and enjoy Lake Tranquility !!

Top guest favorite

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

5 out of 5 average rating, 204 reviews

Rustic Farmette Studio w/Pool & 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.

Top guest favorite

A calm pond is depicted, surrounded by lush greenery and trees. Sunlight reflects off the water, creating a shimmering effect. Lily pads are visible on the surface, with a rustic stone pier in the foreground, adding a natural touch to the serene landscape.

Cabin in Thompson

4.99 out of 5 average rating, 148 reviews

Secluded cabin w/ Finnish Sauna & Forest Baths

A secluded, romantic, rustic, cabin alongside the French River - Frog Hollow is a perfect place to get away and experience the luxury of a wood fired sauna and forest baths. Located in the Quiet Corner of CT, relax as you watch the ducks, herons, turtles, and beavers along the river. Cook a delicious meal in the porch-enclosed kitchen, cozy up next to the woodstove fireplace, work remotely with a water view, or go for a paddle on the river. Ideal for a couple or solo traveler wanting to unwind.

Guest favorite

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

4.93 out of 5 average rating, 385 reviews

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 FREE Oatmeal bar HIGH SPEED WI-FI Pack N Play Glider for nursing/feeding moms! SMART TVs in 2 bedrooms Enjoy a cute stay in quiet neighborhood, 7 minutes from Sturbridge exit (84).

Guest favorite

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

4.95 out of 5 average rating, 122 reviews

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!

Top guest favorite

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

4.98 out of 5 average rating, 178 reviews

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.

Guest favorite

A wooden deck offers high-top chairs facing a tranquil lake surrounded by trees. The scene includes a spacious grassy area leading to the water, with a gazebo visible in the distance. A gentle mist adds a serene quality to the landscape.

Home in Union

4.84 out of 5 average rating, 155 reviews

Antique Home w Private Pond, Sturbridge /Brimfield

Minutes to Sturbridge, great craft breweries, (including TreeHouse), Brimfield Antique Flea Market. Our recently ( and ongoing) renovated 1800s farm house is ready for your next stay. It is quirky and not for perfectionists! Visit nearby Old Sturbridge and its many great shops and restaurants, and nearby State Parks. Plenty of room, fully equipped kitchen, comfy living rm & big dining room. 3 comfortable bedrooms upstairs. Very easy off/on the highway to be on your way quickly!

Top guest favorite

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

4.99 out of 5 average rating, 208 reviews

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.

Top guest favorite

The living room showcases a comfortable seating area with a dark couch, complemented by a glass dining table nearby. A wooden mantel above a decorative fireplace adds warmth, while natural light filters through the large windows, illuminating the soft white walls.

Apartment in Ashford

4.97 out of 5 average rating, 256 reviews

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.