Travel

10 Jaw-Dropping New England Vacation Homes

Rental platform Vacasa has no shortage of inviting hideaways.

Photos courtesy of Vacasa

It seems there’s never a wrong time to duck out from your responsibilities for a week. Vacations are always in season, and in New England, that could mean escaping to the coast or heading up north to the mountains.

A Portland, Oregon-based rental platform called Vacasa offers both—it has hundreds of getaway options in New England for groups large and small. While the company provides rental management for thousands of homes across the country, its selection of vacation homes in New England is top notch.

Here, find 10 of Vacasa’s most stunning rental homes. Rates and fees vary by occupancy, season, and length of stay, so enter dates in the rental calendar for an accurate price estimate.

Photo courtesy of Vacasa

1. Beauty and the Beach on Chapoquoit Island
Falmouth, Mass.
4 bedrooms, accommodates 10 guests

This bayfront home on the Cape offers access to three private beaches, where spectacular sunsets unfold over the horizon. The more than 2,500-square-foot manse is bright and airy, and has plenty of windows overlooking the ocean.

Photo courtesy of Vacasa

2. Sampson’s Folly
Barnstable, Mass.
6 bedrooms, accommodates 14 guests

Built in 1793, the Josiah Sampson House is on the National Register of Historic Places. With six bedrooms, a huge kitchen, and plenty of living space, it’s the ideal spot for the whole family (and then some) to soak in New England’s time-honored charm.

Photo courtesy of Vacasa

3. The Looks Pond Garden House
West Tisbury, Mass.
4 bedrooms, accommodates 7 guests

Nestled near Looks Pond, this guest house on Martha’s Vineyard is sunny and comfortable. It boasts beautiful gardens and views of the water.

Photo courtesy of Vacasa

4. Artist’s Waterfront Retreat
Newburyport, Mass.
2 bedrooms, accommodates 4 guests

This classic saltbox home is chock full of historic charm. It’s only a mile to downtown Newburyport, yet it retains a tranquil atmosphere that’s best suited for painting watercolors.

Photo courtesy of Vacasa

5. Grandeur On The Green
Kennebunkport, Maine
5 bedrooms, accommodates 14 guests

This vibrant home in coastal Maine is situated across from a golf course. Bright colors and sumptuous furnishings adorn the interior, while a sizable patio and a pergola await outside.

Photo courtesy of Vacasa

6. Stunning Coastal Retreat
Falmouth, Mass.
5 bedrooms, accommodates 12 guests

A coveted Cape Cod hideaway, this luxurious home in East Falmouth is a few minutes from the beach. The house is bedecked in stylish coastal accents, and has ample space for entertaining.

Photo courtesy of Vacasa

7. Pedra Estate
Ludlow, Vt.
5 bedrooms, accommodates 10 guests

When winter rears its head, you can ski in and ski out of this contemporary estate up north. The place is a short drive from Okemo Mountain Resort and Green Mountain National Forest, and features a huge dining room with a chandelier.

Photo courtesy of Vacasa

8. A Home with a View
Falmouth, Mass.
2 bedrooms, accommodates 4 guests

This house in Falmouth puts a modern twist on the classic woodland lodge. The stylish abode at the edge of Jenkins Pond comes with a private hot tub.

Photo courtesy of Vacasa

9. Seaport Signal Building
Boston, Mass.
1 bedroom, accommodates 4 guests

Fancy a staycation in a luxe loft? This mod unit in the Seaport’s Signal Industries Building gives you access to a stunning roof deck, not to mention giant windows that frame views of the city.

Photo courtesy of Vacasa

10. Glorious Gingerbread Victorian Cottage
Oak Bluffs, Mass.
5 bedrooms, accommodates 13 guests

Ripped straight from the pages of a fairytale, this colorful cottage on the Vineyard boasts a playful wraparound porch. The gingerbread-style Victorian continues its pastel palette on the interior, right down to the pale pink kitchen.


Madeline Bilis Associate Editor at Boston Magazine @madelinebilis
mbilis@bostonmagazine.com


In This Section

View the Current Issue of Boston Home

View the Current Issue of Boston Home

Best of Boston Home 2017

Best of Boston Home 2017

Our 10th annual guide to the finest local designers and resources in the region.

Inspiration Galleries

Inspiration Galleries

Inspiration for your home: stunning local kitchens, solutions to combat cabinet clutter, and more!