Top 15 Vacation Rentals in Massachusetts

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Lots of people travel to Massachusetts to check out the exciting and historic city of Boston, but there are many other amazing places to visit in Massachusetts for small-town charm, a taste of farm life, and getting back to nature. As an alternative to a standard hotel, you can book a vacation rental property in Massachusetts through Airbnb or Vrbo.

Here are some of the most popular and highly-rated vacation rentals to consider for your next trip to Massachusetts.

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The Clearing Hilltown Cottage, Close to Nature - Hampshire County
Vrbo.com
Overlooking a river and so pretty in the fall

The Clearing Hilltown Cottage, Close to Nature - Hampshire County

When you want to experience the natural side of Massachusetts, book this 700-square-foot cottage with one bedroom and one bathroom. It accommodates four people and sits on top of a hill overlooking the Wild and Scenic Westfield River. There are many birds and wildlife around the property and nearby opportunities to hike, mountain bike, cross-country ski, and snowshoe. Some of the best cross-country skiing in Western Massachusetts is located nearby. The owner of the property lives on site and in the main home that is near the cottage.

Clean, Spacious In-Law Suite Near Everything - Lynn
Airbnb.com
A beautifully furnished space for your stay

Clean, Spacious In-Law Suite Near Everything - Lynn

This Airbnb vacation rental is an in-law suite with one bedroom and one bathroom to accommodate two guests. It also has a dining room/kitchen, living room, and location steps from the Lynn Woods Reservation, with more than 30 miles of trails. This kid-friendly rental comes with a baby crib and toys for kids if you would like them. You’ll have access to three levels of living space and can enjoy the front porch and serene setting. The Airbnb host family lives upstairs above this suite and has a young child.

Romantic Views of the Ocean/Boston with Exclusive Hot Tub - Swampscott
Airbnb.com
Romantic Views of the Ocean/Boston with Exclusive Hot Tub

Romantic Views of the Ocean/Boston with Exclusive Hot Tub - Swampscott

Here’s a highly-rated Massachusetts Airbnb for two people looking for romance in a true hideaway. This Airbnb unit is 12 miles from Boston and has an oceanfront setting. The home is spread across two levels and allows you to easily walk to shops, restaurants, and beaches. It is located on a hill and offers impressive views from every window. Other features of the home are a chef’s kitchen, dining room, Jacuzzi in one of the bathrooms, and fireplace. There is also a private hot tub here to enjoy a soak.

Green Turtle I Houseboat in Boston Harbor - Boston
Vrbo.com
Make this unique spot your base for exploring Boston

Green Turtle I Houseboat in Boston Harbor - Boston

For a truly unique way to experience Boston, consider booking this houseboat rental in Boston Harbor. This rental is a 300-square-foot houseboat that sleeps two people. It is in a gated and secured marina in Boston’s Charlestown neighborhood. From the houseboat, you can walk to restaurants and see the historic sites. The houseboat has two separate suites, but each one is very private and a separate rental. Inside the rental unit, you’ll have a kitchenette and a private bathroom. Sit outside on the dock to enjoy the views and feel the motion of the sea as you float above the water.

Charming Farmhouse, Quiet, Private, and Peaceful - Hampshire County
vrbo.com
Your very own escape in the hills

Charming Farmhouse, Quiet, Private, and Peaceful - Hampshire County

For a quiet and peaceful trip in Massachusetts, book this farmhouse rental that sleeps six people. The home has three bedrooms and 1.5 bathrooms and is well-maintained for your serene, country escape. Two of the bedrooms have queen-size beds, and one bedroom has two single beds for guests. From here, you can get to Northampton within a half-hour drive. Guests will enjoy beautiful views in every direction and a very private place to unwind and enjoy life’s simple pleasures. You may see wildlife on the property and have easy access to hiking opportunities in the region.

Traditional Log House Near Cape Cod - Plymouth
Airbnb.com
You'll love the serenity of this wooded property

Traditional Log House Near Cape Cod - Plymouth

Four travelers can stay in this Massachusetts log cabin and have two bedrooms and one bathroom to themselves. The home is close to the historic town of Plymouth, the Cape, and beaches. You’ll be on an acre of wooded property across from walking trails and cranberry bogs. People love staying here for summer vacations and in the autumn to see the fall foliage. The rental space is on a double-lot property shared with the host’s tiny house/office/workshop. Features of this home include a large outdoor deck with a gas BBQ, complimentary coffee and tea, a pool table and PS3 system in the basement, and large TV with free streaming services.

A-Frame in Sherwood Forest - Becket
Vrbo.com
Step outside to enjoy the yard space

A-Frame in Sherwood Forest - Becket

For up to five people, there’s the option of renting this Massachusetts cabin with one bedroom and one bathroom. This is an A-frame cabin on a ½ acre wooded lot with no close neighbors on three sides. You can walk to a lake from this rental home to go fishing, swimming, and relaxing on the beach. It is within the Sherwood Forest and is accessed by dirt roads. When you stay here, you’ll feel like you’re a million miles away from the real world. One dog of any size can stay with you for a $75 pet fee.

Sweet & Cozy "Rosebud Cottage” - Dennis Port
Airbnb.com
Cape Cod vibes in a great location

Sweet & Cozy "Rosebud Cottage” - Dennis Port

A solo traveler will love staying at this studio rental in Cape Cod that gives you the quintessential Cape Cod experience. It’s in a great location close to a bike trail, the beach, live music, a market, yoga, and an ice cream parlor. This separate and private studio has Wi-Fi, parking, an outdoor seating area, and lovely gardens outside. You can have a wonderful retreat experience at the Rosebud Cottage and make yourself at home here.

Upper Cape Cozy Cottage - Bourne
Airbnb.com
Simple and cozy with everything you need

Upper Cape Cozy Cottage - Bourne

Travelers can rent this simple cottage on an acre of land when they are in the Bourne area of Massachusetts. It is close to the Airbnb host’s main house and has one bedroom, one bathroom, a small kitchen, a TV, games, books, and puzzles. Meanwhile, the outdoor area has a large backyard with yard games, a fire pit, a basketball hoop, seating, and a charcoal grill. It’s an excellent spot for up to three people and has a queen-size bed and couch. When you stay here on the Upper Cape, you can easily get to the Outer Cape, islands, and coastal area of Plymouth.

Your Home for the Holidays - Salem
Airbnb.com
A ground-floor rental with plenty of space

Your Home for the Holidays - Salem

There are many Airbnb options in Salem, Massachusetts, including this rental for two people. It has one bedroom with a queen-size bed and one bathroom, as well as a convenient location near downtown Salem. You’ll stay in an apartment on the ground floor of the main house and have your own private access in the back. The rental includes a living room, dining room, kitchen, and multiple TV options. The property has lots of hand-crafted ironwork surrounding the large lot with a garden. The Airbnb host provides guests with a simple breakfast in the morning and clean linens.

Swan Pond Cottage on the Waterfront with Open Floor Plan - Dennis Port
Vrbo.com
Check out this amazing waterfront view!

Swan Pond Cottage on the Waterfront with Open Floor Plan - Dennis Port

The Swan Pond Cottage is a Vrbo vacation rental property that is 1,000 square feet in size and has two bedrooms and one bathroom. It sleeps five people and allows you to kayak or paddleboard down Swan Pond River to Nantucket Sound and Great Island. Guests love the location of this property because it is also a short distance from hiking and biking trails. The sleeping arrangements are a king-size bed, two twin beds, a three-seat sofa, and a full futon. Other features of the cottage are laundry machines, internet, flat-screen TV, a gas grill, and beach supplies. This pet-friendly Cape Cod rental encourages you to bring furballs along with you.

City Oasis with Deck & Yard - Cambridge
Airbnb.com
Sit outside and enjoy your own personal space

City Oasis with Deck & Yard - Cambridge

You can walk to the Harvard MIT Train from this Cambridge home, a popular option for up to three travelers. It has a queen-size bed in the bedroom, a pull-out queen bed in the living room, and one bathroom. You’ll be on a quiet residential street and have central A/C. There’s also a recently renovated eat-in kitchen, a deck with a grill and seating, and a yard for guests. Laundry machines are available in the unit, but no parking is available with this rental.

Historic Home with Ocean Views - Buzzards Bay
Vrbo.com
A beautifully decorated home with original features

Historic Home with Ocean Views - Buzzards Bay

For large groups, there’s the option of renting this 2,000-square-foot home with four bedrooms and 2.5 bathrooms in one of New England’s best beach vacation destinations – Buzzards Bay. The rental house sleeps ten people and is an easy walk from a public beach. The historic home has many original features, plus modern conveniences, such as a flat-screen TV, cable, internet, and a laundry room. All the bedrooms are upstairs, and the wrap-around porch is great for sipping drinks as you watch the sunset. Guests also enjoy the large backyard at this property and the gas grill and hot outdoor shower in the back.

Idyllic, Private Country Retreat - Buckland
Airbnb.com
Rustic and perfectly cozy for two

Idyllic, Private Country Retreat - Buckland

Two people can book this Massachusetts Airbnb and stay on the beautiful grounds of an 1815 farmhouse. This rental is a one-room cottage with a sleeping loft and private bathroom. It’s on 23 acres of woods and rolling meadows near the charming small towns of Shelburne Falls and Northampton. There is no Wi-Fi in the cottage, but you can access Wi-Fi in the barn and sitting area in front of the farmhouse. Feel free to help yourselves to fruits, vegetables, and flowers on the farm during your stay as you wander through the gardens.

Adorable Free-Standing Cottage at Beach Point - Provincetown
Airbnb.com
By the water and with everything you need

Adorable Free-Standing Cottage at Beach Point - Provincetown

Available to rent on Airbnb, this cottage is a highly-rated studio space for two people in Provincetown, one of New England’s cutest beach towns. The home has one bedroom and one bathroom, as well as a full kitchen, Wi-Fi, Roku TV, and heat/air conditioning. You can go for a walk down the footpath to reach the bay beach and enjoy being in a quiet neighborhood off Shore Road. Guests who book this Airbnb will need to bring their own bath towels, bed sheets, and beach towels.

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