If vacationing with long-lost friends or relatives is in your future, these fantastic Airbnb rentals for groups near Boston make planning that much-needed getaway too easy to pass up. They’ve got everything groups need for a comfy stay including lots of space, activities within walking distance and of course, pools. Here’s where to gather your friends and family for an unforgettable vacation.
Idyllic House Across from Seth’s Pond | West Tisbury, MA
Ferry over to Martha’s Vineyard to enjoy this renovated farmhouse with your group. Just across from Seth’s Pond and about half a mile from Lamberts Cove Beach, families will find all they need create memories. The property sits on over two explore-able acres and the lawn games, gas grill and fire circle will keep your combined crews outside on late summer nights. Nearby Polly Hill Arboretum is another place to explore.
Sleeps: 11
Cost: $785/night
Online: airbnb.com
1790 Historic Stone Manor | Hopkinton, MA
Turn back the clock on your group vacation plans when you stay at this New England home. It combines history with modern updates (kitchen and baths were updated in 2020) and it’s less than an hour's drive from the city. The outdoor pool and hiking around the property’s four acres will keep the kiddos happy. And everyone will enjoy post-dinner s’mores around the firepit when dinner’s over.
Sleeps: 10
Cost: $350/night
Online: airbnb.com
Broom & Board | Salem, MA
Even if witches aren’t your thing, this modern townhouse in the heart of Salem will bewitch your group. Downtown Salem, with all its history and attractions, is just a five-minute walk. Go the other direction, and you’re at Salem Willows where the kids can arcade it up all morning long before hitting the nearby public beach for the afternoon. Then it’s off to pick up lobster rolls and fried clams for dinner.
Sleeps: 10
Cost: $387/night
Online: airbnb.com
Iconic Cabin in the Berkshires | Sanisfield, MA
Settle into this rustic cabin set on eight acres in the Berkshires to get away from it all. Parents can do yoga and swim in the endless indoor pool located in the spa room, and everyone will enjoy playing pool and darts in the billiards lounge. Dinner prep is easy in the spacious kitchen with two ovens. Outdoor activities include hiking on the nearby Appalachian Trail and canoeing the Farmington River.
Sleeps: 12
Cost: $993/night
Online: airbnb.com
Pirate’s Hideaway on the Nubble | York, ME
Just a short walk from the Nubble Lighthouse, you’ll find this four-bedroom home that welcomes pirates and mermaids of all ages. Kids will go gaga for the amazing ocean-themed touches they’ll find in the house (who knows, maybe there’s even treasure!), while parents will enjoy the proximity to beaches and creature comforts that make this space feel like home. Check out nearby Mt. Agamenticus for trailside adventures beyond the beach.
Sleeps: 12
Cost: $550/night
Online: airbnb.com
Year-Round Mountain Home | Stockbridge, MA
Although you’ll find everything you need at this gem of a house, including a pool, pool house and gazebo, getting out to explore the area should be on your to-do list during your stay. The Normal Rockwell Museum, Edith Wharton’s House and the Berkshire Botanical Garden are all close by. And there’s excellent skiing for winter stays. There’s every reason to get the gang together at this abode.
Sleeps: 12
Cost: $1,300/night
Online: airbnb.com
West Barnstable Resort | Barnstable, MA
Who needs a resort when you and your besties can rent this six-bedroom home? It’s got everything you need to re-create a resort vacay without the crowds. Spend time outside swimming in the pool or playing tennis on the backyard (lighted) court. Indoor activities include pool and a home theater, complete with popcorn popper and enough seating for all your kids. Then, after the kids go to sleep, parents can enjoy the hot tub on the back deck.
Sleeps: 14
Cost: $1,100/night
Online: airbnb.com
Gloucester Ocean View Home | Gloucester, MA
If an ocean view and relaxing atmosphere are on your group travel list, this 3,000-square-foot home should do the trick. The porch overlooks the Atlantic and Thatcher Island, and Good Harbor Beach is just a short walk away. Explore the trails and sights of Halibut Point State Park when you stay.
Sleeps: 12
Cost: $550/night
Online: airbnb.com
The Driftwood | Kennebunk, ME
Spend time on Gooch’s Beach, just across from this seven-bedroom house that’s within walking distance of Dock Square shops and restaurants. Gather for dinners on the front porch and then retire to the living spaces for a round of cards or a favorite board game before turning in for the night. All that’s left is a trip to Auntie’s House for a classic whoopie pie.
Sleeps: 11
Cost: $450/night
Online: airbnb.com
Cape Cod Home with a Pool | East Falmouth, MA
You’ll find the touches of home at this rental that’s just a hop skip and a jump away from the beach where Jaws was filmed back in the day. The kids will spend plenty of time splashing in the heated outdoor pool, before they head downstairs for ping pong, air hockey and foosball. Nantucket is just a short ferry ride away when you need another adventure.
Sleeps: 10
Cost: $639/night
Online: airbnb.com
Historic Inn Turned Home | Hampton, NH
You’ll find all the space you need for your group at this spot that’s less than a mile from the beach. After all, it used to be an inn. But you don’t have to be a road-weary traveler to enjoy time here. Everything your group needs to enjoy the nearby beach is here, including a boogie board. And the screened in porch is perfect for group game night or pre-dinner gatherings when the weather is warm.
Sleeps: 10
Cost: $495/night
Online: airbnb.com
—Allison Sutcliffe
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