Holiday rentals in Middleborough

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Top-rated holiday rentals in Middleborough

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Guest favourite
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.
Flat in Bridgewater
4.84 out of 5 average rating, 268 reviews

Sun-Drenched 2BR Near Cape Cod & Boston Commuter

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 favourite
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, 161 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 favourite
The exterior of the residence showcases a two-story design with a steeply pitched roof and shingle siding. Lush green shrubs and trees frame the entrance, while a gravel path leads to the welcoming front steps. A clear blue sky adds to the inviting ambiance.
Guest suite in Plymouth
4.97 out of 5 average rating, 65 reviews

`Unique and private in-law!

1 bedroom in-law apartment, with an open full kitchen and living area. One bedroom, one private bathroom, and one office with desk. Private deck and patio. Free parking on premises. Private entrance with lockbox. Quiet neighborhood that has cranberry bogs and trails for walking. Host lives on premises. Prime location between Cape Cod and Plymouth center! 45 mins south of Boston 5 minutes from the Cape Cod Canal 15 minutes to Plymouth Center 5 minutes away from beach/ocean with free parking!

Top guest favourite
A view of a serene outdoor space featuring a green lawn bordered by a cranberry bog. A fire pit with chairs is situated in the foreground, while a rustic building and tree line create a picturesque backdrop under a cloudy sky.
Guest suite in Duxbury
4.94 out of 5 average rating, 107 reviews

Guest suite on cranberry bog, 1 mile from beach

Why fight the traffic to Cape Cod when you can enjoy New England's beaches, trails and seafood from beautiful Duxbury - just an hour from Boston! Our home is on a gorgeous cranberry bog surrounded by biking and walking trails and just a mile from the beach. Skylights and french doors to a private patio fill the suite with sunlight. Guests enjoy the fire pit, grill and yard in summer or hit the trails on snow shoes and sleds in winter. The bog freezes over too and is great for ice skating!

Top guest favourite
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, 57 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 favourite
Guest house in Freetown
4.9 out of 5 average rating, 10 reviews

The Knotty Witch Waterfront Retreat w Full Kitchen

Escape to the tranquil beauty of the Assonet River with a stay in this charming second-floor getaway. The home features a covered deck that's perfect for enjoying your morning coffee or unwinding in the evening while taking in the stunning views. You'll find a spacious living space and a fully equipped kitchen, providing everything you need for a relaxing getaway. This serene retreat is perfect for business travel, couples or families looking for a peaceful escape. Travel nurse friendly.

Guest favourite
Flat in Carver
4.92 out of 5 average rating, 12 reviews

Charming Retreat Amidst Carver’s Cranberry Bogs

Escape to the Heart of Cranberry Country! Nestled in the quaint town of Carver, Massachusetts – the self-proclaimed “Cranberry Capital of the World” – our two-bedroom apartment offers the perfect blend of cozy comfort and authentic New England charm. Kitchen is fully equipped, Wi-Fi, smart TV, and parking for two cars, you’ll feel right at home. The space sleeps up to 4 guests comfortably (5 with futon). Step outside, and you’re yards from Carver’s walkable working cranberry bogs!

Top guest favourite
The exterior of a welcoming home is shown, featuring a porch with elegant front doors. Soft lighting illuminates the entryway, while lush greenery and colorful flowers enhance the landscape, providing a warm and inviting entrance.
Flat in Pembroke
4.99 out of 5 average rating, 144 reviews

Beautiful Lakeside Apt between Boston and Cape Cod

Beautiful apartment, with extraordinary lake views, located on a quiet street and midway between Boston and Cape Cod. Access to the lake is just feet from your back door. Enjoy grilling, swimming and the use of kayaks, canoe and standup paddle boards. 1 bed, 1 bath, can sleep 5 with a pull out queen and twin couches. Full kitchen, laundry, internet, cable. Your own access with keypad and off street parking is an added bonus. NO SMOKING OF ANY KIND IN OR OUTSIDE-NO EXCEPTIONS.

Superhost
The exterior of a cozy cabin is displayed, featuring white siding and decorative wooden shutters. A simple stone pathway leads to the front door, surrounded by well-maintained greenery and blooming flowers, all under a clear blue sky.
Cottage in Lakeville
4.69 out of 5 average rating, 94 reviews

Cozy Lake cabin Boston/Providence/Cape Cod

This cozy cabin is located just steps away from beach access to Long Pond, one of Massachusett's largest fully recreational Lakes. Newly renovated kitchen/bath. Beds feature luxurious sleeping accommodations including UGG bedding. The backyard features a seating area/fire pit and grill. Pets welcome Centrally Located!! 45 minutes outside of Boston 25 minutes away from Cape Cod and the ocean. 30 min from Providence Rhode Island 2 hours from the White Mountains of New Hampshire.

Superhost
A serene lakeside view features calm waters reflecting pastel hues of the sunset. Smooth stone pathways lead to a grassy area, where comfortable seating arrangements are visible. The landscape is framed by trees, adding a natural element to the tranquil outdoor setting.
Home in Lakeville
4.87 out of 5 average rating, 75 reviews

Lakefront Retreat -Private Dock+Kayaks on the Lake

Escape to Long Pond, Massachusetts’ premier fully recreational lake. This beautifully renovated 3-bedroom, 2-bath waterfront retreat features a private dock plus kayaks, canoe, rowboat, and paddleboard for your enjoyment. Swim, boat, jet ski, fish, water ski, tube, or simply relax by the water. Conveniently located within 30-45 minutes of Cape Cod, historic Plymouth, downtown New Bedford, beaches, restaurants, and many of Southeastern Massachusetts’ top attractions.

Top guest favourite
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.
Guest house in East Providence
4.95 out of 5 average rating, 123 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.

Superhost
A lakeside view of a charming home with large windows, surrounded by lush greenery. A stone patio features seating arrangements with a pink umbrella, while the shoreline is visible in the foreground. Calm waters reflect the structure, enhancing its serene atmosphere.
Home in Lakeville
4.76 out of 5 average rating, 38 reviews

Shoreline Dreams

Welcome to your dream vacation getaway! Nestled on the serene shores of Long Pond, this charming lakefront home offers the perfect blend of comfort and natural beauty. Step inside to a spacious, open-concept living area adorned with large picture windows that provide breathtaking views of the sparkling water. Outdoor chairs with firepit offer panoramic views of the lake. The private dock is perfect for swimming, fishing, or launching kayaks and paddleboards.

Popular amenities for Middleborough holiday rentals