
Vacation rentals in Massachusetts
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Top-rated vacation rentals in Massachusetts
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Vacation rentals for every style
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Popular amenities for Massachusetts vacation rentals
Massachusetts oceanfront vacation rentals

Oceanfront Vacation Home with Private Beach for 6

Spacious waterfront free parking &Wi-fi

Lovely Day Oceanside

Buzzard Bay Getaway

Old Wharf Rd 405 Unit #B303

Waterfront gem

Breathtaking Views, Oceanfront home on the Beach

Spacious 2BR Steps To Beach. 2.4 miles to Salem 28
Pet-friendly vacation rentals in Massachusetts

2-Bedroom Pet-Friendly Farmhouse Suite

Clear Pond Pet Friendly Inn

Beach Cottage, without going over bridges to Cape!

Sweet Cottage w/ yard, 1.5BR, Walk to Town & Water

Cabin @ Newcomb Hollow Beach

Eastham Escape

Walk2Beach, HotTub, FirePit, PetsOk

Shirley's Place - Pet Friendly Sleeps Six!
Massachusetts fishing vacation rentals

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Fabulous Waterfront! 3bdrm/2bth Kayaks & Firepit

Idyllic family retreat - spacious lake home,

Direct Lakefront Home on Otis Reservoir Giant Yard

Water Front Pond House - 3 acre Cape Cod Sanctuary

Berkshire Lake- Modern and Updated-close to skiing

Onset beach, Cape code.Private Waterfront cottage

Brimfield Lakeside Home Away from Home
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
- Beachfront rentals Massachusetts
- Chalet rentals Massachusetts
- Waterfront rentals Massachusetts
- Cottage rentals Massachusetts
- Rentals with a home theater Massachusetts
- Farmstay rentals Massachusetts
- Beach house rentals Massachusetts
- Guesthouse rentals Massachusetts
- Pet-friendly rentals Massachusetts
- Rentals with an EV charger Massachusetts
- Condo rentals Massachusetts
- Rentals with pools Massachusetts
- Private suite rentals Massachusetts
- Rentals with beach access Massachusetts
- Rentals with outdoor seating Massachusetts
- Barn rentals Massachusetts
- Fitness-friendly rentals Massachusetts
- Ski-in/ski-out rentals Massachusetts
- Rentals with a kayak Massachusetts
- Luxury rentals Massachusetts
- Rentals with a sauna Massachusetts
- Lakehouse rentals Massachusetts
- House rentals Massachusetts
- Villa rentals Massachusetts
- Bed and breakfasts Massachusetts
- Rentals with lake access Massachusetts
- Rentals with a hot tub Massachusetts
- Rentals with an accessible height bed Massachusetts
- Loft rentals Massachusetts
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- Rentals with a fireplace Massachusetts
- Mansion rentals Massachusetts
- Bungalow rentals Massachusetts
- Serviced apartment rentals Massachusetts
- Hotel rentals Massachusetts
- Apartment rentals Massachusetts
- Townhouse rentals Massachusetts
- Family-friendly rentals Massachusetts
- Boutique hotel rentals Massachusetts
- Rentals with a washer and dryer Massachusetts
- Smoking-friendly rentals Massachusetts
- Rentals with a patio Massachusetts
- Cabin rentals Massachusetts
- Kid-friendly rentals Massachusetts
- Tiny house rentals Massachusetts
- Rentals with an accessible height toilet Massachusetts
- Rentals with a fire pit Massachusetts
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- Things to do Massachusetts
- Sightseeing Massachusetts
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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