Vacation rentals in Middleborough

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Top-rated vacation rentals in Middleborough

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Guest favorite
A living room area is depicted, featuring a green sofa and a wooden TV stand. Skylights allow natural light to fill the room, highlighting the warm wooden floor. In the background, a small kitchen can be seen through an open doorway, with two stools arranged at a counter.
Apartment in Bridgewater
4.84 out of 5 average rating, 258 reviews

Charming New England 2brm Apt. South of Boston

Welcome to a bright, comfortable 2-bedroom apartment just a 4-minute walk to BSU. Perfect for visiting families, traveling nurses, professors, and corporate guests. Enjoy private driveway parking, Wi-Fi, a fully equipped kitchen, and quiet residential neighborhood with a spacious backyard. located near Good Samaritan Medical Center and the VA, with easy access 2 Boston, Gillette Stadium, Plymouth, Rhode Island, & Cape Cod. A peaceful, homelike alternative 2 hotels for short or extended stays.

Top guest favorite
The entryway features a wooden staircase with white railings leading to the second floor. A cozy seating nook sits beside a window, adorned with decorative pillows. Light-colored walls complement the hardwood flooring, while a console table with a decorative bowl adds a welcoming touch.
Home in Plymouth
5 out of 5 average rating, 150 reviews

Updated Antique in Historic Downtown Plymouth

Updated antique colonial within walking distance to everything historic Downtown Plymouth has to offer- waterfront, boating, shops, restaurants, historic sites, and more. Fenced in backyard with patio overlooking gorgeous, well-maintained garden. Patio has large farm table with umbrella and Weber grill, great for entertaining! This charming in-town location offers you the best of both worlds - walking distance to everything while also being cozy and comfortable to enjoy a day at home to relax.

Top guest favorite
A stunning sunset paints the sky with vibrant colors reflected in the calm water of Woods Pond. The outdoor deck features seating arrangements, while two fishing poles stand ready for use by the private dock. Trees frame the serene view, adding a natural touch.
Home in Middleborough
5 out of 5 average rating, 46 reviews

Pelicans Bog on Woods Pond in Middleboro

Centrally located in Middleboro, this 3 bedroom house on Woods Pond is in a private community. Enjoy the massively spacious out door space while you fish directly off your private dock in the water. Kayak the pond with 2 tandem kayaks provided. Enjoy breezy dinners on the elevated deck overlooking the pond. There is an Air Hockey table located just off the basement bonus room or the foosball table inside. A dedicated large office space fully equipped and minutes to MBTA 1 hour to Boston.

Guest favorite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon
4.95 out of 5 average rating, 216 reviews

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Top guest favorite
A welcoming living area features comfortable electric recliners and a small table, set against neutral-colored walls. A nautical-themed rug lies on the floor, while wall art and colorful flags add character. Natural light flows in through the window, which is adorned with blinds.
Tiny home in Mattapoisett
4.99 out of 5 average rating, 129 reviews

101 Steps to Beach/Island/Bike Path

Experience the Seaside Town of Mattapoisett. Location! Relax in this cozy cottage that is 101 steps from the front door to the Beach/Island/Bike Path. Enjoy this popular, sought after scenic Path for walking, biking, or a day at the Beach. The path is known for its picturesque coastal views. Walking distance to the Quaint Town, Shipyard Park, and many restaurants. Ned's Point Lighthouse- 5min. Day trip to the Vineyard? Ferry- 14 min. Season Open! Early Bird- 15% off of Sept! 3 days-10% off.

Top guest favorite
A spacious living area features a light-colored sofa with decorative pillows, a coffee table, and a television mounted on the wall. Large sliding glass doors allow natural light and provide a view of the outside deck. A lamp adds a subtle touch of illumination.
Condo in Plymouth
4.99 out of 5 average rating, 124 reviews

Captain's Lodge- #1, Plymouth Water Front Condo

1200 square foot condo. 2 bedrooms plus loft. 1 +1/2 baths. Full large eat in kitchen + dinning and living room area. Massive outside deck over looking Plymouth harbor. Located in the heart of the historic Plymouth Water front. Short walk to the rock, Mayflower and beaches and surrounded by resturants , pubs and night life. Location offers access to all that Plymouth has to offer. Condo has been recently remodeled and everything is new and clean. Off street parking on location.

Guest favorite
The kitchen features stainless steel appliances, including a refrigerator and a gas stove. Light grey walls are complemented by granite countertops. Natural light enters through a window above the sink, with kitchen essentials and decor items visible on the counters.
Townhouse in Wareham
4.96 out of 5 average rating, 218 reviews

The Gateway to Cape Cod townhouse !

SUMMER 26 AVAIL DATES June 1-5,7-12,21-23 July 13-16, 20-24 Aug 21-23,26-28 BEACH PASS PROVIDED PLEASE CHECK OUT SLEEPING ARRANGEMENTS PRIOR TO BOOKING MAX 6 adults only Ideal for families Parking for 2 vehicles only WELCOME to Wareham! The town with the most coastline out of any town in MA 60 miles! Minutes to Water wizz and TONS of local beaches ! Wareham center and a local grocery store are both walking distance away! Great proximity to Boston , providence , Plymouth, cape

Top guest favorite
The living room features a light-colored sectional sofa adorned with patterned throw pillows. A decorative coffee table sits in front, surrounded by neutral-toned walls. A ceiling fan provides air circulation, while artwork enhances the ambiance. The space is designed for relaxation and entertainment.
Apartment in New Bedford
4.94 out of 5 average rating, 115 reviews

NEAR THE FERRY/ Charming Gem Apt.

This peaceful centrally apartment will make you feel like you never left the your house. The apartment is located on the 2nd floor, Is cozy,comfortable and ideal for (2 adults and 1 child or 4 adults. The place have 1 Queen bed and 1 SLEEPER SOFA. This place is only 10 min away from ferry station to Martha's Vineyard and others Islands, 30 mins from Providence RI and 45 mins from Boston. The Charming Gen is only 10mins away from Dartmouth and the Downtown Of New Bedford.

Top guest favorite
An open-concept studio is displayed, featuring a spacious bed with a light gray blanket. A cozy seating area includes a sofa and a chair, while a dining table is positioned in the background. Large windows allow natural light to illuminate the checkered floor.
Guesthouse in Rumford
4.96 out of 5 average rating, 101 reviews

Beautiful Studio - < 15 mins 2 downtown & Brown

Relax, work, and unwind in “The Treehouse,” our serene, light-filled studio apartment nestled among the trees. Perfectly located in historic Rumford, RI, it’s just 3 miles from Brown, RISD, and Johnson & Wales, and 5 miles from Providence College. Enjoy quick access to the East Side of Providence, Newport, and Little Compton beaches. Conveniently close to Amtrak, bus lines, and the airport, it’s an ideal spot for exploring New England or visiting area colleges.

Top guest favorite
A handcrafted tree house is perched among trees, supported by wooden stilts. The structure features a rustic exterior with a metal roof and large windows, surrounded by greenery and vibrant pink flowers in the foreground, creating a serene and natural setting.
Treehouse in Wareham
4.97 out of 5 average rating, 223 reviews

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

Guest favorite
A deck area features a grill on a tiled surface, surrounded by two wicker chairs and a small table. Vibrant red flowers in a planter add color, and trees provide a natural backdrop in the distance.
Apartment in Plymouth
4.83 out of 5 average rating, 227 reviews

Captains Quarters

A Bright and sunny home with two bedrooms, a spacious living area with an open kitchen and dining room to enjoy family fun. This home is perfectly located in Plymouth where tourism options are endless, ten minutes away from Plymouth beach, downtown Plymouth and the waterfront area or explore the south side of Plymouth fifteen minutes away from manomet beaches pine hills golf course and others. Cape Cod beaches approx half hour away.

Top guest favorite
A serene view of a spacious home set against a backdrop of lush greenery and wildflowers. The house presents an inviting facade with multiple windows, surrounded by the natural beauty of the landscape, creating a sense of tranquility.
Guest suite in West Falmouth
4.99 out of 5 average rating, 214 reviews

The Ideal Spot

The perfect getaway in Falmouth for all seasons! Our home is beautifully located overlooking Bourne’s Farm and we are steps away to the picturesque Shining Sea Bike Path. Enjoy a beautiful scenic 8.5 mile ride winding your way thru the Sippewisset marsh and along the coastline to the seaside village of Woods Hole. Where you can enjoy the local restaurants ,shops and science learning or jump on the ferry to Marta’s Vineyard.

Popular amenities for Middleborough vacation rentals