Holiday houses in Massachusetts

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Top-rated holiday rentals in Massachusetts

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

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Guest favourite

Home in Rockport

5 out of 5 average rating, 43 reviews

New South End Home Quiet Lane To Old Garden Beach

Newer furnished home, 1/2 mile walk to quaint Bearskin Neck with Rockport shops & galleries. Old Garden Beach 1/4 mile walk down a quiet unpaved lane. 3 BR/3 Bath home available for summer weekly vacations. Family friendly, 3 prkg spaces, 2 decks, new appliances (laundry, microwave & dishwasher), hardwood floors, new rugs & beds, full basement w/ pool table, fenced yard. Several beaches, hiking trails nearby or take a train to Salem, Newburyport, or Boston. Longer term winter rental available

Guest favourite

Apartment in Oak Bluffs

4.95 out of 5 average rating, 167 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, 212 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

Home in Edgartown

4.91 out of 5 average rating, 53 reviews

Updated Beautiful Cottage in Edgartown AC

Inquire about transferable ferry tickets. Light, airy and central-air-conditioned home offers all the comforts of modern living centrally located in Edgartown. A true island charmer. 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.

Guest favourite

Home in Mashpee

4.94 out of 5 average rating, 35 reviews

Tranquil Cape getaway#2 with AC Kid & Pet friendly

Welcome to this peaceful Cape retreat! With its charming Cape style home and serene surroundings, this two-level residence offers a perfect getaway for relaxation and quality time with loved ones. Property Features: Four Cozy Bedrooms Outdoor Deck and Grill Complete Fenced-In Yard Swing Set Whether you're looking to relax indoors, enjoy outdoor activities, or spend quality time with family and friends, this idyllic haven offers all the necessary amenities for a memorable vacation.

Guest favourite

Home in Scituate

5 out of 5 average rating, 19 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!

Guest favourite

Cottage in Newburyport

4.93 out of 5 average rating, 108 reviews

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

Guest favourite

Guesthouse in Provincetown

5 out of 5 average rating, 67 reviews

Central Cottage -Incredibly Located, 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 full 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 Scituate

4.83 out of 5 average rating, 58 reviews

Sand Hills Beach - lighthouse area -

Walking distance to sand hills beach - One mile from center of town with restaurants and shops. Nearby basketball court. Very Close to Barker Tavern. Grassy backyard . New furnishings new full bath and new mattresses. bedrooms are upstairs. There is only one full bath upstairs Totally redone 2024. Bungalow beach style home. some guests find stairs to be “ steep” … my 82 year old mom does fine with the stairs and rail!

Guest favourite

Home in Great Barrington

5 out of 5 average rating, 6 reviews

Winter Holiday & Ski Season Rental!

Charming, cozy cottage, walking distance to Lake Mansfield and Main Street attractions, 20 minutes to Tanglewood, 15 minutes to area summer camps or the Zipline at Catamount Ski Area. Freshly renovated throughout, fully-equipped kitchen, large yard with screened dining porch. Comfortable and stylish home in a centrally-located spot. Attention to all the little details.

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!!

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.