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

Chic Downtown Loft ☆ Private Parking ☆ Ocean View
The light and water and pedestrians out on the harbor are constantly changing - we loved sitting in Alex's beautiful space and looking out. They even happened to have the town's Memorial Day celebration right out our window. The space is serene, filled with light, and cozy. The entry door and stairs call for smaller bags (e.g. airplane carry-on roller bags), which is what we had, so we had no trouble. The A/C and heat kept the space comfortable in spite of some substantial temperature swings outside. The parking spot is about a 5-minute walk and a lifesaver, given how the parking in town fills up instantly... and Alex said this was calm compared to later in the season. Being able to stop right by the house to drop off and pick up bags made it very easy. Also be sure to try the small boiled lobsters at Roy Moore - they were super. Thank you, Alex!!

Baker Pond Hideaway
Kathleen and Mike were greats hosts. They welcomed us when we arrived and gave us clear communication about what areas we were welcome to use. Their property is a peaceful, beautiful spot on the lake. We will definitely stay there again when we come back to the area!

Cozy Cottage in the Berkshires
Have stayed in Sonya’s cottage many times and each time is better than the last. Definitely the place I check for first when in the area.

Little Boho Retreat by the Beach
Felicia and Little Boho Retreat by the Beach deserve all the raving reviews. In all honesty I wish I could give more than five stars. The cottage is cozy, well-stocked, and every attention to detail is notable. Felicia thought of everything. The cottage is a destination in and of itself, to say nothing of the wonderful places we visited on The Cape, as well as Plymouth, Wareham, and Marion. I feel like there is so much more to do and experience on Dexter Beach and in this area. We definitely would like to return to this spot.

WOW VIEW! Waterfront w/ Private Beach, King Bed!
Fantastic few days spent relaxing by the lake. Views were beautiful and the home is exactly as shown in the photos. Everything from start to finish was just right. Will definitely stay here again in the future.

Oceanfront Pool. Close to Boston. Free Parking.
We loved their place and the location right on the beach and in the sea wall . Got great pics of waves hitting the seawall. Close to alll Boston and Salem locations . Had a great time apt was beautiful and Carol and John left fridge for us fully stocked with milk juice drinks and food . Couldn’t ask for more . We thoroughly enjoyed the hot tub Grest place to stay

Rocky Neck Studio/Loft, Gloucester, Mass.
Mary and Dave’s place was the perfect little spot for our visit to Cape Ann. Small but everything you need. The neighborhood was so peaceful, they really have a gem here. The hosts were very welcoming and gave lots of local recommendations. Loved getting to pet Penny and Indy in the mornings too! We would definitely stay again.

Beachfront Cottage on White Pond (Marshmallow)
This place was beautiful. Loved the private pond. The house is in the woods, and I loved that. The Host was great. Very helpful. This was exactly what I wanted. Relaxation, beautiful views and just all around quiet. I went with my BFF and she loved it. I Definitely will be back!!
Massachusetts fishing vacation rentals

Fabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
Serene and charming riverfront hideaway. In a residential neighborhood but very quiet. You are 5-10 minutes from great restaurants, shopping, Dennis Beach but it all feels very secluded. We went kayaking every day from the private dock, saw swans, sea lions, and hawks. The space is clean, boho-chic, very comfortable beds, easy to use gas fireplaces. Primary bedroom sitting area/sunroom is dreamy for reading. Kitchen has everything you need. We thought we might miss an ocean/bay view but we didn't at all. Very reasonably priced for the quality. Meg replied to all messages within minutes. We would absolutely come back. Great for a couple or small family.

Berkshires Cottage by Lake. Year Round Adventures.
Had a great stay at Scott’s cottage. Felt right at home It was very comfortable and clean.

Lakefront House Boston, Plymouth, Cape Cod
Absolutely beautiful views & setting overlooking the water. We loved our short, but very lovely stay here. The kids (and us!) loved the finished downstairs area w/ bedroom and bathroom!

The Lake Cottage: A Sweetwater Stay
Excellent and beautiful location. Very scenic and tranquil. The location allows you to relax while still being in reach of everything. The unit was very well maintained and clean. All the Amenities of home without the chaos.

Charming Pond-Front Boathouse
Adorable boathouse tastefully furnished right on the water. Lynn was so accommodating and helpful. The spot was peaceful and cozy - we had a wonderful stay.

Sunrise on the Water's Edge - Riverside Bungalow
Well equipped, clean, functional space. Back porch and patio is fantastic for expanding the space and ease of entertainment. Caught some pretty good catfish and carp right off the back stairs/landing. Convenient to many amenities with easy access from rt159 and rt57.

The Breeze Overlooking Minister's Pond
Tara’s spot was beautiful, and private. We loved having access to the e-bikes. The rail trail was close by and we biked on it and walked on it to dinner one night. Tara’s spot was a perfect spot to hang out and to come back to after a busy day. The weather wasn’t conducive to hanging out on the deck but it was a lovely set up. Would highly recommend.

Artsy Pine Cabin in the Woods
Could not recommend this tiny cabin any more, certainly an enviable artist's retreat! Our hosts made sure that we were well-welcomed, and an eastern phoebe and chorus of wood frogs kept us company throughout our stay. Kerry really looked out for us during our weekend there, and it was a pleasant surprise to encounter her art not only in the cabin, but also down at the Bookmill!
Home rentals in Massachusetts

Nana-tucket Inn
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.

Juniper Point Cottage With Ocean View
We loved our stay here. It worked well for two groups. The view was amazing and we had a fair amount of wildlife visit us. Very walkable down to cure coffee shops and restaurants and also right off the bike path. Devon was a fantastic host and very accommodating! Would stay again!

Newly renovated, spacious, clean, 3 bedroom home.
Our rental was roomy with 6 adults and slept comfortably with bedrooms were big and roomy. The coffee station was great with everything we needed. William was there to greet us and allowed us an early check in to drop off luggage before enjoying the area. Lots of towels and toiletries. The place was very clean and enjoyed the snacks. Thanks.

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK
We had a very relaxing stay at this property. Very comfortable bed and home. Staying on the pond was very calming. Though the weather did not allow us to use the kayaks, we could see that it would have been fun. Host was very responsive and helpful. Fabulous stay! Highly recommend this great place!

Seaview Summit | Ocean Views, Indoor Pool, Beach
This house was spectacular. More amenities than I would have ever thought of. Gorgeous interior and exterior. The surrounding neighborhood is in need of regentrification but it’s extremely safe and quiet. Once in the home., it’s an oasis. Probably the best Airbnb I’ve stayed in (sample size about 10) Tony is extremely responsive and helpful. This was the perfect home for my daughter’s bridal party to get ready in and shoot pre wedding photos in. Also amazingly comfortable for my large family to stay in for the long weekend.

Jaw dropping mountain & lake views
Excellent stay at this beautiful house! The views were spectacular and everything was as described in the listing.

Newly Built, Stunning, Lake Front Retreat!
Gary’s home is beautiful. We especially enjoyed the covered porch and Adirondack chairs that overlooked the water. The house was spotless both inside and out! The kitchen is well stocked with everything that you will need to prepare a meal. Thank you for sharing your home Gary!

Sunny Chalet Nestled in the Woods of Ashfield
Loved our stay ... We had a nice family dinner , could sit out on deck and enjoy the gorgeous view and our meal and then were able to take a short hike up the back trails and enjoy the gardens and store .... Hannah was awesome and very responsive and checking in to make sure that we were all set .. Thank you so much for allowing us to stay and enjoy our stay. We had a perfect weekend. Thank you, Garry and Family
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
- Cottage rentals Massachusetts
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- Waterfront rentals Massachusetts
- Rentals with an accessible height toilet Massachusetts
- Rentals with a fire pit Massachusetts
- Bed and breakfasts Massachusetts
- Rentals with a patio Massachusetts
- Rentals with a washer and dryer Massachusetts
- Chalet rentals Massachusetts
- Rentals with pools Massachusetts
- Smoking-friendly rentals Massachusetts
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