Vacation rentals in Middleborough

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Top-rated vacation rentals in Middleborough

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Top guest favourite
A spacious bed is centered against a light grey wall, featuring a wooden headboard. Colorful coral-patterned pillows add a subtle touch. Two bedside tables with lamps sit on either side, creating a balanced and calming atmosphere.
Home in Mattapoisett
4.94 out of 5 average rating, 235 reviews

*The Cozy Escape* | Historic South Coast Retreat

SAVE (heart) US NOW! Escape to Mattapoisett on the South Coast of MA & experience the charming beauty of this small town! Our recently updated home is a perfect retreat for your getaway. Take in the stunning views of the harbor at Shipyard Park or stroll along the area beaches. Explore the area's history at Neds Point Lighthouse & Salty the Seahorse. Unwind at our cozy & inviting home. Dine in with our fully equipped kitchen or indulge at the many great restaurants! Book your unforgettable stay!

Guest favourite
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
4.78 out of 5 average rating, 120 reviews

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.

Top guest favourite
The kitchen area features modern stainless steel appliances, including a gas range and a dishwasher. A granite countertop is prominently displayed, alongside an assortment of cooking oils and spices on the shelves above. A kettle rests on the stovetop, adding functionality.
Loft in Wareham
4.94 out of 5 average rating, 174 reviews

The Gateway to Cape Cod Loft!

SUMMER 2026 is OPEN BOOK QUICK JULY 4th 2026 OPEN! Christmas 2025 open! 24-28th BEACH PASS PROVIDED PLEASE READ GREAT FOR FAMILIES Can sleep a 6th SMALL CHILD (5 or under) in this unit if needed 5 adults MAX parking for 2 cars only WELCOME to Wareham, the town with 60 MILES of shoreline in Massachusetts! Minutes away from Water wizz and TONS of local beaches. Wareham Center and a local grocery store are both walking distance away! Near Plymouth and Cape, Boston and providence, RI

Top guest favourite
A cozy living space features a striped sofa and a round table set near a rug. Light from the windows brightens the room, which leads to a bedroom visible in the background, adorned with a patterned quilt and vibrant pillows.
Cottage in Pocasset
4.98 out of 5 average rating, 320 reviews

Upper Cape Cozy Cottage

Simple but cozy cottage on an acre property next to the main house. Moderate sized bedroom and living room. Small kitchen and bathroom. The kitchen is fully equipped for cooking. Air conditioning is a portable unit and only in the bedroom. Games, books, and puzzles provided. There is no cable but a smart TV is included with access to Netflix etc. if you have an account. Outdoor area includes charcoal grill and seating . Large back yard with yard games, basketball hoop and fire pit.

Guest favourite
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 homes in Pembroke
4.86 out of 5 average rating, 130 reviews

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 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.

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.
Apartment in Bridgewater
4.83 out of 5 average rating, 246 reviews

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!

Superhost
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.
Guest suite in Bridgewater
4.83 out of 5 average rating, 209 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.

Superhost
A renovated antique house is displayed, featuring a three-story structure with a green and cream exterior. Large, multi-pane windows are positioned prominently on the front, and a distinctive red trim highlights the architectural details. A small front garden area is visible.
Apartment in Federal Hill
4.82 out of 5 average rating, 635 reviews

Clean Studio Apt. #5 on Federal Hill, Providence

Charming small, self contained studio apartment on the 3rd floor of newly renovated antique house. Warm in Winter, cool in Summer. Fast internet and TV with Netflix. Fully equipped kitchen, full bath/in-bath shower. Quiet neighborhood with coffee shops, restaurants and bus stop literally around the corner. Easy, 15min walk to downtown/Convention Center /Bus/Train stations/Mall. 10mins walk to the famous Atwells Avenue and all it's wonderful restaurants.

Guest favourite
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
4.89 out of 5 average rating, 164 reviews

Lovely Lakeside Cottage

Keep it simple at this peaceful and centrally-located cottage. Lovely lakeside cottage with open floor plan. Centrally located in southeastern Massachusetts with short drives to Boston, Providence, Newport, and Cape Cod. Several beaches within 20 minutes. Washer/ Dryer on site and California King Size bed. A simple five (5) minute ride to UMass Dartmouth. Cottage has a living room, full kitchen, bedroom, full bath, and small dining area.

Top guest favourite
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
5 out of 5 average rating, 48 reviews

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.

Top guest favourite
A modern kitchen is showcased, featuring navy blue cabinetry and wooden countertops. Equipped with a stainless steel refrigerator, oven, and a farmhouse sink, the space includes a toaster and coffee maker. Shelves display dishware, while bright light enhances the welcoming atmosphere.
Apartment in Mattapoisett
4.99 out of 5 average rating, 139 reviews

Brand new! Whole apartment, huge tub, full kitchen

Beautiful self-contained apartment. Enjoy the blissful extra-long Kohler soaking tub, rain shower, and luxurious Matouk towels. Full kitchen and outdoor seating area. DreamCloud queen bed. Short walk to the center of the village and town wharf, providing easy access to all of Mattapoisett's charm, including Ned's Point Lighthouse and Town Beach. Outstanding local restaurants and sweet treats all close by.

Guest favourite
The kitchen features wooden cabinetry and a countertop with a sink and stove. A coffee maker and organized spice jars are visible. Decorative items, including a wall sign and an art piece, enhance the space. A textured rug lays on the floor in front of the sink.
Apartment in New Bedford
4.93 out of 5 average rating, 328 reviews

Exquisite Apartment in New Bedford

Modern apartment right in downtown New Bedford! If you are looking for a place where you can walk to everything you need, then this is your spot. It is a modern, first floor apartment with brand new furniture. If you don't want to walk, no worries, we have off street parking so we will save your spot.

Popular amenities for Middleborough vacation rentals