Holiday rentals in Massachusetts

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Top-rated holiday rentals in Massachusetts

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

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

Superhost

Cottage in Fairhaven

4.83 out of 5 average rating, 213 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!!

Superhost

Home in Scituate

4.83 out of 5 average rating, 58 reviews

Sand Hills Barker Tavern RiverClub lighthouse -

Walking distance to sand hills beach - super close to BARKER TAVERN! One mile from center of town with restaurants and shops. Nearby basketball court. Grassy backyard . New furnishings new full bath and new mattresses. Freshly painted well maintained by owner 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 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!

Guest favourite

Home in Plymouth

4.93 out of 5 average rating, 41 reviews

Serene Lakefront Retreat: Your Perfect Getaway!

Escape to our serene lake house with breathtaking views & endless opportunities for outdoor adventure. With a dedicated workspace, stay connected while enjoying tranquility. Take a paddle on the lake with kayaks & pedal boat, or relax on the patio with outdoor fire pit. Fully furnished & decorated, feel at home cooking in the fully equipped kitchen or curling up in the cozy living room. Book your stay today and experience the magic of nature firsthand!

Guest favourite

Guest house 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 queen bed, outdoor seating area, shared backyard (with seating, grill, and outdoor shower), and reliable high-speed wifi. Fresh, whimsical styling & worldly charm.

Guest favourite

Cottage in Newburyport

4.93 out of 5 average rating, 110 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.

Superhost

Home in Edgartown

4.91 out of 5 average rating, 53 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.

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.

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