
Massachusetts vacation rentals
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Top-rated vacation rentals in Massachusetts
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Home in Barnstable
4.86 out of 5 average rating, 140 reviewsCottage 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!!!

Home in Sheffield
4.9 out of 5 average rating, 115 reviewsWow! Best BERKSHIRE SnowHome #1 Private SuperClean
"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Cottage in Fairhaven
4.83 out of 5 average rating, 213 reviewsCottage 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.

Home in Sandwich
5 out of 5 average rating, 22 reviewsThe Cape Cottage-Fireplace*Kid Friendly*Pets OK
The Cape Cottage is a private, tranquil Cape Cod style cottage nestled near historic downtown Sandwich and just 6 minutes from the ocean. Newly renovated, this home is tastefully designed with a blend of coastal, farmhouse and antique design elements. We thoughtfully curated the home's details to evoke the comforts of home & give it unique charm that pays homage to Cape Cod's scenic beauty & quintessential New England. Check out our IG @thecapecodcottage for more pictures.

Home in Scituate
5 out of 5 average rating, 20 reviewsCoastal 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!

Home in Plymouth
4.93 out of 5 average rating, 41 reviewsSerene 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!

Guesthouse in Provincetown
5 out of 5 average rating, 67 reviewsCentral 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.

Cottage in Newburyport
4.93 out of 5 average rating, 109 reviewsSunset 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.

Home in Edgartown
4.91 out of 5 average rating, 53 reviewsUpdated 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.

Home in Great Barrington
5 out of 5 average rating, 6 reviewsWinter 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.

Home in Orleans
4.89 out of 5 average rating, 57 reviewsRomantic 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!!

Cottage in Oak Bluffs
4.96 out of 5 average rating, 147 reviewsBeautiful clean walk to Town, Inkwell and harbor!
This elegantly decorated beach cottage that was constructed this year. It provides all the amenities for a relaxing vacation. As your host we supply beach chairs, towels and umbrella, a fully equipped kitchen, outdoor shower and entertaining space with a gas grill, WiFi, sheets and towels all within minutes of fabulous shopping, restaurants, and activities.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts vacation rentals
Massachusetts waterfront vacation rentals

Home in Sandwich
5 out of 5 average rating, 190 reviewsQuintessential Waterfront Historic Cottage

Home in Yarmouth
5 out of 5 average rating, 290 reviewsgorgeous waterfront cottage w/4kayaks and 2 SUPs

Apartment in Oak Bluffs
4.88 out of 5 average rating, 153 reviewsWATERFRONT PENTHOUSE OAK BLUFFS

Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 339 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit

Home in Dartmouth
4.87 out of 5 average rating, 31 reviewsSerene 4BR/3BA Waterfront Getaway & Dock

Cottage in Sturbridge
4.93 out of 5 average rating, 148 reviewsCozy Cottage on Cedar Lake- "Cottage Cheeze"

Condo in Provincetown
4.96 out of 5 average rating, 184 reviewsBayshore 9 Waterfront Renovated Condo with Parking

Home in Dennis
4.87 out of 5 average rating, 509 reviewsBeachfront Cottage on White Pond (Marshmallow)
Massachusetts fishing vacation rentals

Cottage in Orange
4.89 out of 5 average rating, 111 reviewsThe Film Shack: A Sweetwater Stay

Cottage in Orange
4.93 out of 5 average rating, 167 reviewsThe Lake Cottage: A Sweetwater Stay

Cabin in Hubbardston
4.94 out of 5 average rating, 155 reviewsTriggers Cabin

Cottage in Lanesborough
4.97 out of 5 average rating, 64 reviewsAmazing 2 bedroom lake front cottage, large patio

Home in Otis
4.96 out of 5 average rating, 107 reviewsDirect Lakefront Home on Otis Reservoir Giant Yard

Home in Westminster
4.82 out of 5 average rating, 136 reviewsLakefront, view of ski mtn, firepit, kayaks, dock

Home in Brewster
4.87 out of 5 average rating, 200 reviewsWater Front Pond House - 3 acre Cape Cod Sanctuary

Home in Wales
4.96 out of 5 average rating, 27 reviewsCharming water front cabin with boat dock
Home rentals in Massachusetts

Home in Rockport
5 out of 5 average rating, 3 reviewsRockport Vacation Home, ocean views, 2 bed/1 bath

Home in Yarmouth
4.94 out of 5 average rating, 141 reviewsCape Cod Life is Good Rentals

Home in Shrewsbury
5 out of 5 average rating, 10 reviewsLake "Island"

Home in Wellesley
4.76 out of 5 average rating, 17 reviewsVintage home with modern conveniences

Home in Cohasset
4.9 out of 5 average rating, 30 reviewsVillage Colonial with Cohasset Harbor Views

Home in Westport
4.85 out of 5 average rating, 104 reviewsBeach Home – Family Friendly - Solar Powered

Home in Vineyard Haven
5 out of 5 average rating, 59 reviewsWell-Appointed 3 Bedrm 4 Bathrm w/ 50+ 5* Reviews

Home in Boston
4.96 out of 5 average rating, 111 reviewsLargeDuplex10Beds w/prkg near Downton
Your guide to Massachusetts
All About Massachusetts
Massachusetts’ bustling capital, Boston, draws in travelers seeking to explore the city’s extensive history, legendary baseball stadium, and impressive arts scene — but this northeastern state offers varied geography and options beyond its biggest city. There are opportunities for outdoor adventure, rest and relaxation, and arts and culture throughout the state. Western Massachusetts and the Berkshires is the state's rural mountain region popular with ski resorts and snow-shoeing for outdoor athletes. The towns and many farms of the central region host fall harvest celebrations and farm-to-table dining with some of the state’s best fall foliage driving routes.
Sturbridge Village is ideal for history buffs wanting a glimpse into life in New England during the 19th century. Cape Cod, a hook-shaped peninsula abou 70 miles south of Boston, is known for its beautiful beaches and lighthouses. Beachgoers and island lovers can take a ferry to the islands of Nantucket and Martha’s Vineyard for swimming, surfing, and miles of bike trails. The state’s rich maritime tradition is evident in the northern coastal towns of Newburyport, Rockport, and Marblehead.
Boston is rich in history and culture — dine at one of its award-winning restaurants or make your way through the Freedom Trail, which weaves through the city passing iconic sites of the American Revolution and gorgeous green spaces like Boston Commons and Public Garden.
The best time to stay in a vacation rental in Massachusetts
Fall is an excellent time for a trip to the state, bringing bright, colorful foliage and the chance to meander down the scenic Route 2 highway from Boston to western Massachusetts. There are hot, humid summers and snowy, cold winters here, weather typical for most northeastern states. Summers also come with intense thunderstorms, but that doesn’t stop people from enjoying the beaches or heading to the Berkshires for Tanglewood’s summer music lineup.
Massachusetts is susceptible to hurricanes from June until November, though the majority weaken to tropical storms as they pass by the state. Winters are milder along the coast, with temperatures staying above freezing even in January. As you move further inland, it gets colder, and snowfall in the mountains is perfect for skiing and snowshoeing. Spring is generally wet and cloudy across the state, but let that stop you from exploring the Brimfield Antique Show, the largest antiques show in the country.
Top things to do in Massachusetts
Explore the History of Lexington
Drive 20 minutes outside Boston to the birthplace of the Revolutionary War. Hop on the Liberty Ride Trolley and pass multiple pivotal historical sites. Favorite stops include Lexington Battle Green — where the first shot of the Revolutionary War was fired in 1775 — and significant literary sites from classic American writers.
The Berkshires
Located on the far western border of the state, The Berkshires are popular with outdoor enthusiasts, artists, shoppers, and foodies. Known for the mountains and ski resorts here, it's a winter wonderland for skiers, snowboarders, and even offers snow tubing. Once the snow melts, you’ll find epic hiking trails, white-water rafting, and climbing opportunities abound. Towns throughout the area including Lenox, Great Barrington, Stockbridge, offer farm-to-table restaurants, antique shopping, unique musical experiences, and local theatres.
Western Massachusetts wineries
Explore picturesque vineyards while sipping on award-winning wines from dozens of wineries across Western Massachusetts. A rising star on the global wine stage, the area's wines are hand-crafted from a variety of grapes, fruits, berries, and even flowers. The region’s most common grape varieties are the vinifera varieties including chardonnay, pinot grigio, riesling, and pinot noir. Many of the wineries can be found between Amherst and Springfield with stunning landscapes to enjoy along the way.
Destinations to explore
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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes