Holiday rentals in Middleborough

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Top-rated holiday rentals in Middleborough

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Flat in Oak Bluffs

4.92 out of 5 average rating, 109 reviews

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

Guest favourite

Home in Hyannis Port

4.87 out of 5 average rating, 149 reviews

Cottage with private beach in Hyannis Port

Make your Cape Cod trip unforgettable in this Exclusive Harbor Village Cottage located right in Hyannis! Enjoy this recently updated 2-bed, 2-bath vacation home with access to private beach, beautiful outdoor deck, and peaceful ocean views. Follow the beach path 900 feet to the beach! Only minutes from downtown Main Street, the Melody Tent and Hyannis harbor. Whether you spend your days exploring the Cape, sunbathing on the beach, or relaxing on the deck, you will be sure to love this house!!!

Superhost

Home in Yarmouth Port

4.88 out of 5 average rating, 153 reviews

* Walk to the beach - Swiss Beach House! *

Walk to the beach! Less than a 1/2 mile (0.7 km)! Perfect spot for paddle boarding. Paddleboards and gas grill (available in summer). Private European - style house. Rustic charm. Laid-back atmosphere. 3 Bedroom, 2.5 bathroom. Comfortably sleeps 6-7, up to 8. Fire pit. Outdoor shower. Farm table for group dining. Fantastic central Cape Cod location. Natural environment. 15 min. to Hyannis for ferries to Nantucket or Martha's Vineyard. Enjoy something unique. Experience the real Cape Cod.

Guest favourite

Flat in Oak Bluffs

4.95 out of 5 average rating, 168 reviews

Beautiful private apartment walk to everything!

This is an incredible property! Renovated and spotless with all the amenities to make your stay feel like home, only better. Downtown Oak Bluffs and her beautiful beaches are within a five-minute walk. There is a local market and deli right next door where you can find anything you need in a pinch, and a great BBQ restaurant across the street. This second floor apartment has one bedroom with a queen-sized bed and a queen pullout couch. Smart TVs, full kitchen and laundry plus much more!

Superhost

Cottage in Fairhaven

4.83 out of 5 average rating, 218 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.

Superhost

Cottage in Brewster

4.85 out of 5 average rating, 62 reviews

BeachFront Private Beach Amazing Views WIFI

Sunset Cottage, Amazing Location on a secluded bluff, with fantastic views of Cape Cod bay, Beach front! A/C WIFI Simple Cottage, natural setting, safe quiet clean Beautiful huge Private beach for 3 cottages and the main house. All photos are on the property Desirable Brewster MA on the Bay. Amazing sunset views over the ocean from every room. Full kitchen, large living room, Master Queen bedroom, 2nd queen bedroom (coolgel matress), Long wide private beach. 360 feet long!!

Top guest favourite

Home in Scituate

5 out of 5 average rating, 20 reviews

Coastal Retreat

Welcome to our coastal rental, a charming retreat nestled in the heart of a vibrant beach town. With modern amenities and coastal decor, unwind in the light-filled spaces and savor beautiful marsh views from the well manicured backyard. Located about a mile from Main Street, you can walk or bike on the flat sidewalk to restaurants, shops and the harbor. Close by you'll also find a dog park, the beautiful public golf course, Widow's Walk and of course the beach!

Top guest favourite

Guest house in Provincetown

5 out of 5 average rating, 67 reviews

Central Cottage-Incredible Location, Stylish Charm

Beautifully renovated cottage in incredibly central Provincetown location! Less than a block to The Boatslip and the beach! Open studio cottage has stunning tile throughout, kitchenette, excellent air conditioning, ceiling fan, living area with couch, breakfast bar/desk, farmhouse sink, 1 queen bed, outdoor seating area, shared backyard (with seating, grill, and outdoor shower), and reliable high-speed wifi. Fresh, whimsical styling & worldly charm.

Superhost

Home in Edgartown

4.91 out of 5 average rating, 54 reviews

Updated Beautiful Cottage in Edgartown AC

A true island charmer. Light, airy and central-air-conditioned home offers all the comforts of modern living centrally located in Edgartown. Recently completed extensive upgrades completed enhance all of the space, including a new kitchen, both bathrooms, basement, and more. A spacious outdoor furnished deck with enclosed outdoor shower and an expansive grassy lawn make for a great space to relax. Great location makes Island travel a breeze.

Superhost

Home in Orleans

4.89 out of 5 average rating, 57 reviews

Romantic Orleans waterfront cottage

ENHANCED CLEANING/DISINFECTING and SELF CHECK-IN ! The best of Cape Cod - literally on the edge of the gorgeous and picturesque saltwater town cove! This beautiful 1BR cottage is clean, comfortable and private, ... yet within a short walk to village center, shops, great eateries, attractions, etc. We just added propane fire pits and bluetooth speakers outside!!

Top guest favourite

Home in Yarmouth

5 out of 5 average rating, 24 reviews

Cape Cod Retreat

Recently updated Cape Cod vacation home close to everything in the heart of South Yarmouth beach neighborhood. Nantucket Sound and Bass river beaches just a short walk away. Close to Forest Rd bike path leading to the CC Rail Trail. Top Cape restaurants and many amenities just a few blocks away.