Vacation rentals in Middleborough

5 out of 5 average rating, 50 reviews

A sandy beach area is visible in the foreground, adjacent to a calm lake. A cottage is seen in the background, set among trees. Steps lead from the cottage to the beach, enclosed by a fence. Seating areas and kayaks rest nearby.

Cottage in Taunton

Lakefront Cottage w/Private Beach

Come stay in our cozy lakefront cottage. Outdoor deck w/dining table that leads to a fully fenced in backyard w/outdoor shower and private beach. 2 Single Kayaks available to use! Centrally located but quiet. Located down a dead end street on Lake Sabbatia. 10 Miles to Xfinity Center 17 Miles to Patriot Place&Gillette 29 Miles to Providence 39 Miles to Boston Currently set up as a 1 bedroom w/an office. Second “bed” is an extra thick futon in the sunroom. Follow us @sabbatiacottage

5 out of 5 average rating, 34 reviews

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

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.

4.78 out of 5 average rating, 115 reviews

A cozy living area is presented with a dark couch and a wooden dining table accompanied by black chairs. A TV is situated on a light-colored media unit, while bookshelves filled with books line one wall. Natural light filters in through sheer curtains.

Apartment in Fairhaven

Main Street on the Park

Welcome to Main Street on the Park! The morning sun will greet you in the bright apartment in our big white house with a yellow front door. Perfect for a romantic getaway or a convenient place to stay if you are in the area for business. A large fenced yard abuts a public park complete with tennis courts, track and walking trail. Explore our small town with a big history, visit its historic buildings, great restaurants and unique shops. The location is convenient to all of the South Coast.

4.85 out of 5 average rating, 122 reviews

A small, red-roofed structure is visible in the foreground, surrounded by a neatly maintained grassy area. A white fence encloses the space, with trees and lush greenery present in the background. Two horses can be seen grazing peacefully, adding to the serene rural setting.

Tiny home in Pembroke

Tiny farm house on horse farm

Set in a quiet cul-de-sac at the end of our driveway, this tiny house is part of our family compound and working horse farm. We have and many animals. Enjoy your space, knowing we are just 50 yards away should you need anything. This is a true tiny house experience. The kitchenette has everything you need. The sleep loft is accessible by a ladder and has a low ceiling. Disclaimer there is no door on the toilet, which is tucked away in the kitchen area. WiFi connection is not guaranteed.

5 out of 5 average rating, 3 reviews

A bright living area features vaulted wooden ceilings and an inviting neutral color palette. Two contemporary lounge chairs and a plush sofa are arranged around a wooden coffee table adorned with books. Light enters through multiple windows, illuminating the space and providing a view of the outdoor greenery.

Cottage in Marion

The Salt House • Private Beach

A fully remodeled, design-forward beach cottage just a two-minute stroll from a private beach framed by unforgettable golden-hour sunsets. Inside, vaulted ceilings, natural light, and luxury furnishings set the tone for a stay that’s both elevated and easy. Enjoy a chef’s kitchen with custom Bosch appliances and bedrooms outfitted with luxurious linens and mattresses. Outside, a quaint private backyard with a sitting and dining area is ideal for morning coffee or dinner under the stars.

5 out of 5 average rating, 18 reviews

A charming yellow house with blue shutters and a welcoming front door is surrounded by greenery. A comfortable seating area is positioned on the front deck, complemented by a pathway leading to the driveway. Adjacent lighting adds ambiance in the outdoor space.

Home in Lakeville

The Shore House

Welcome to The Shore House. Our little peace and quiet getaway. This cozy little two bedroom one bath house has a nice calming water view. Sit on the the front deck and have your morning coffee. Go for a stroll on the quiet little private roads of this vacation location. The Shore House has a nice water view of Long Pond, which is on of Massachusetts largest fresh water ponds and it’s largest recreational pond. There are three beaches on the pond to enjoy within 200 yards of the house.

4.83 out of 5 average rating, 230 reviews

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

Charming New England 2brm Apt. South of Boston

Inviting 2-Bedroom Apartment in Quintessential New England Town Bright & Airy – Skylights fill the cozy living room with natural sunlight. Fully Equipped Kitchen – Compact yet functional with all essentials. Comfortable Bedrooms – 2 well-appointed rooms for restful sleep. Private Driveway & Free Parking Spacious Backyard –Perfect 4 relaxing. Prime Location – 4-minute walk to Bridgewater State U. Ideal 4-Family, travel nurses, healthcare workers, and corporate stays. Book now!

4.75 out of 5 average rating, 20 reviews

A modern kitchen features sleek black cabinetry and a spacious central island. Four tall, rounded stools are arranged around the island. Stainless steel appliances, including a refrigerator and oven, complement the design. Large windows let in natural light, enhancing the contemporary atmosphere.

Townhouse in Bridgewater

Modern luxurious home 5-beds

Spacious & Comfortable Stay in Bridgewater, MA Welcome to our 2,200 sq. ft. home, perfect for families, business travelers, or groups visiting Bridgewater State University and the surrounding area. Located in a quiet neighborhood, our home offers a peaceful stay while being just minutes from local Bridgewater State University, restaurants, shops, and major highways. Whether you’re here for work, school, or leisure, you’ll enjoy a comfortable and well-equipped space to call home.

Guest suite in Bridgewater

A small entryway features a black panel wall with hooks for hanging. A tufted gray bench provides seating, while a decorative arrangement of pampas grass is displayed in a woven vase. Light artwork adorns the wall, enhancing the welcoming space.

4.87 out of 5 average rating, 187 reviews

Cozy & Modern 3rd floor one bedroom Suite

Welcome to the Cozy Suite! This charming, modern retreat offers a private entrance and everything you need for a comfortable stay. Perfectly situated just 5 minutes from Bridgewater State College, you'll enjoy a peaceful and convenient location with easy access to all the local attractions. Whether you're here for business, a visit to campus, or simply to explore the area, this suite offers a stylish and cozy escape. Ideal for anyone looking for a modern, hassle-free experience.

4.69 out of 5 average rating, 89 reviews

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

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.

4.86 out of 5 average rating, 189 reviews

A cozy studio space features a plush sofa adorned with decorative pillows and a small coffee table. Natural light enters through two windows dressed in neutral curtains, while a nautical-themed bed is positioned nearby, displaying colorful pillows. A patterned area rug adds warmth to the hardwood floor.

Apartment in Marion

Studio Apartment w/sm Kitchen

Studio apartment that is well suited for a couple and young family. Children under twelve years of age will not be charged the extra fee. There is an added fee for extra adults over 2. This is a small space for 3 adults. This is our own home in which the studio apartment is above the garage. This was added for our daughter who attended a local college. She live there for 5 years while attending college.

5 out of 5 average rating, 40 reviews

A spacious living area is fitted with modern, light-colored leather sofas arranged around a round wooden coffee table. Natural light filters through a large window, and a decorative staircase leads to the upper level. A cozy space is created with a plush area rug.

Home in Middleborough

Renovated Home with Family Theater Room and Sauna

Newly renovated house with a fenced in backyard, located near downtown Middleboro, Massachusetts, that is just a short walk to some amazing restaurants and family diners, bars and breweries, shopping and family parks! You will have access to three (3) Bedrooms, a large family room with a pull-out couch, 2.5 Bathrooms, full size Washer and Dryer and a three (3) person Sauna, in addition to a fully stocked kitchen.

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Other great vacation rentals in Middleborough

Private room in Fairhaven

A spacious bedroom features a comfortable bed with soft bedding and decorative pillows. A desk with a chair and a lamp is positioned near a window, allowing natural light to fill the room. A potted plant adds a touch of greenery to the space.

4.88 out of 5 average rating, 553 reviews

Peaceful Suite with a Harbor View

4.91 out of 5 average rating, 127 reviews

Private room in Wareham

Room in private home

5 out of 5 average rating, 123 reviews

A comfortable bedroom features a spacious bed layered with soft linens and a textured throw. Natural light fills the room through a large window dressed with sheer curtains. A ceiling fan provides airflow, while a wall-mounted TV and minimalist decor enhance the serene atmosphere.

Guesthouse in Abington

Cozy In-Law Apartment

A serene ocean view is captured from a bluff, showing a sandy beach below with calm water reflecting the sky. A few figures can be seen walking along the shore, complemented by the distant horizon and scattered clouds above.

Home in Plymouth

5 out of 5 average rating, 3 reviews

Seaside retreat w/ private beach

4.89 out of 5 average rating, 192 reviews

Private room in Kingston

Cozy South-Facing Room with Private Bath

4.91 out of 5 average rating, 22 reviews

The exterior of the home features a gentle sloping lawn with colorful flowering plants framing the entrance. A set of steps leads to the front door, flanked by well-maintained greenery. Large windows allow natural light to illuminate the interior.

Home in Plymouth

Home in Plymouth (Lake Access)

4.89 out of 5 average rating, 145 reviews

Two wooden adirondack chairs are positioned on a grassy area, facing a tranquil lake surrounded by trees. Bright yellow daffodils bloom nearby, adding a touch of color to the natural landscape under a clear blue sky.

Guesthouse in Dartmouth

Lovely Lakeside Cottage