Holiday houses in Middleborough

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.

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.

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.

The Gateway to Cape Cod Loft!

SUMMER 2026 is OPEN BOOK QUICK! Winter has reduced rates! 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 the most COASTLINE out of any town in Mass! A whopping 60 miles! 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

Sunny studio on the East Side!

Quiet, sunny 300 sq foot studio, great neighborhood, on National Historic Register! Close to Miriam, Brown & RISD. You have the entire second floor to yourself, w/ driveway parking, private entrance & bath, lounge, work/eating counter, high speed WiFi & Roku Smart TV. There's a small fridge, microwave, Brio hot/cold filtered water dispenser, Keurig. Coffee, tea, milks, homemade muffins, granola bars :). Please note: GUESTS MUST BE ON THE LISTING. VISITORS MUST BE APPROVED PRIOR TO STAY.

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.

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.

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.

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.

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.

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.

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.