Holiday houses in Middleborough

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Top-rated holiday rentals in Middleborough

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Top Guest favourite

The living room is arranged with a large brown sofa and two blue swivel club chairs. A wooden coffee table sits in the center, accompanied by decorative accents. Light streams in from two windows adorned with sheer curtains, illuminating the hardwood floors.

Apartment in Plymouth

5 out of 5 average rating, 23 reviews

Cozy Space w/ AC & Office, Walk to Beach/ Downtown

Our home is just 500 ft from Nelson Beach, with a splash pad and playground and less than half a mile to popular restaurants and shops. The Mayflower & Plymouth Rock are less than a mile away. Our 2nd floor apartment has central air, hardwood floors and granite counters. There are 3 bedrooms and a small home office. Free high speed Wi-Fi, 2 TV’s with Roku sticks and Netflix, washer & dryer, and 2 off street parking spots. Lockbox for contactless entry. Our home is smoke-vape free and pet free

Top Guest favourite

The cottage exterior is illuminated by warm lights, showcasing a spacious deck with inviting seating. Lush greenery surrounds the property, with a vibrant purple flowering bush nearby. The serene atmosphere is enhanced by the evening sky, providing a cozy and welcoming retreat.

Cottage in Marion

5 out of 5 average rating, 201 reviews

Little Boho Retreat by the Beach

Kick back and relax in the most calming, low charm country, coastal cottage the town of Marion has to offer. You’ll experience spectacular view of the beach right from the deck to watching the boats from the harbor. Don’t just limit yourself to life at the beach in just the summer months, come and make memories in this beautiful year-round cozy cottage. It's a perfect retreat to go swimming, kayaking, fishing, bird/seal/crabs watching and more right here in a private community on Dexter Beach.

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, 40 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.

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 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!

Guest favourite

The exterior of the cottage is shown, featuring a welcoming blue door and a well-maintained front yard with colorful flowers. The view includes a quiet street lined with trees and nearby houses, providing a glimpse of the neighborhood atmosphere.

Cottage in Fairhaven

4.83 out of 5 average rating, 239 reviews

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

Guest favourite

A spacious living area features a green sectional sofa with accent pillows and a coffee table. A light area rug lies beneath. The open design connects to a modern kitchen, visible in the background, with sleek cabinetry and bar seating.

Apartment in Taunton

5 out of 5 average rating, 20 reviews

Stylish Top-floor Retreat

Experience the perfect blend of contemporary design and historical beauty with this newly renovated 1 bedroom 1.5 bath apartment located in the heart of downtown Taunton. Offering a private balcony, modern amenities and prime location. This unit is perfect for professionals, couples or anyone looking for a comfortable urban lifestyle. This stunning unit offers breathtaking views overlooking the iconic Taunton green bringing a touch of history right to your doorstep.

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

A sunlit room features a striped area rug on wooden flooring. A comfortable chair is positioned beside a large window with blinds, offering views of the garden outside. Artwork adorns the walls, adding a touch of color to the space.

Apartment in Norton

4.87 out of 5 average rating, 182 reviews

Artist's Retreat in Norton - no cleaning fee!

This space will make you feel cozy and right at home! A bright and well-appointed apartment located in Norton MA, which is equidistant (30 mins drive) from Boston, Providence, and Cape Cod. We are not wannabe Hiltons, just a settled couple whose house includes an in-law apartment with no in-laws.