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21 Coolest Airbnb Rentals in Massachusetts

Massachusetts offers everything from beautiful beaches and lighthouses to mountains for hiking and tranquil ponds for paddling. Of course, it’s also home to Boston with some of the country’s most impressive historic sites and world-class cultural attractions. No matter what type of vacation you have in mind, there’s sure to be a cool Airbnb for your stay.

Enchanted Tiny Tower at Santarella Gardens - Lee Enchanted Tiny Tower at Santarella Gardens
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Enchanted Tiny Tower at Santarella Gardens - Lee

Looking as if it’s out of a storybook, this enchanting two-story wooden tower house sits on a 4-acre estate in the Berkshires with its picturesque landscapes that include sparkling lakes, scenic hiking trails, and vibrant foliage in the fall. The property itself is filled with gardens, a lily pond, a flowing brook, and a wooded area. The interior has a kitchenette, a canopied queen bed with beautiful forest and pond views, and a 35′ conical ceiling. You’ll even be able to fall peacefully asleep to the sounds of the bubbling brook.

Octagonal Glass Treehouse - Otis Octagonal Glass Treehouse in Berkshires - Otis, Massachusetts
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Octagonal Glass Treehouse - Otis

Ideal for a romantic couples’ retreat, this unique treehouse-style rental is uniquely designed. While you’ll have plenty of privacy, the floor-to-ceiling windows showcase its beautiful unobstructed surroundings in the Berkshires. The large deck off the back is a popular spot to relax, grill, and enjoy outdoor dining, while the wood-burning fireplace inside is fabulous to cozy up to together with a glass of wine. It sits on seven acres with three skiing areas and miles of hiking trails nearby.

The Pondhouse, a Magical Place - Ashfield The Pondhouse
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The Pondhouse, a Magical Place - Ashfield

The Pondhouse offers more of a glamping-style experience that’s ideal for those who want to escape electronics and enjoy time to relax and recharge. With no walls, only screens, you’ll be immersed in nature, enjoying the sounds and sights right from bed. You won’t have electricity, but you will have a composting toilet, outdoor sink and hot shower, and a fire pit for roasting marshmallows under the stars.

Secluded Cabin with Babbling Brook - Monterey Secluded Cabin with Babbling Brook
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Secluded Cabin with Babbling Brook - Monterey

A classic cabin in the woods, this secluded rental sits right next to a stream. A stay here provides easy access to Butternut Ski Mountain, just five minutes away, and offers the chance to fall asleep to the sounds of the rushing water. It includes two bedrooms plus a king loft, accommodating up to six, along with a professional kitchen, a large wood-burning fireplace, a bathroom with a clawfoot tub, and a deck that sits right over the stream.

Quintessential Salem Stay - Salem Quintessential Salem Stay
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Quintessential Salem Stay - Salem

For those who are into all things “witchy” a stay in Salem is a must and this rental for up to four perfectly complements the experience. It’s not only within walking distance to downtown attractions like the Salem Witch Museum, but the main bedroom has dark gothic decor that was “designed to get you in the Salem spirit.” The adjacent room was outfitted to look like a Victorian British library where you can dig into a good book, and you’ll also have a full kitchen, dining room, spacious living room, a full bath, TV, and free Wi-Fi.

Wings Neck Lighthouse - Pocasset Wings Neck Lighthouse
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Wings Neck Lighthouse - Pocasset

Used for nearly a century by the U.S. Coast Guard between the mid-19th and -20th centuries, this lighthouse near the Cape Cod Canal is linked by a breezeway to a three-bedroom home that accommodates up to eight. You’ll have your own stretch of private beach steps away and a 360-degree view of the ocean. By climbing the mahogany spiral staircase to the lantern room in the lighthouse you can take in one of the most spectacular views while learning more about its history. The home has lots of historic charm and includes a living room with a fieldstone fireplace that opens to the spacious kitchen.

The 1770 House - Colrain The 1770 House
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The 1770 House - Colrain

A farmhouse originally constructed in 1770, expanded and transformed into a fabulous designer retreat in the countryside, up to 12 guests can enjoy an unforgettable stay in the 1770 House. It offers 4,500-square-feet of space with six bedrooms located at the end of a dirt road, surrounded by serenity and fabulous views overlooking the Green River Valley. It offers open-plan living with exposed beams, a chef’s kitchen, Dish TV, and Hughes Net, while surrounded by decks, porches, and patios. From May 1 through October 30, you can enjoy the swimming pool and spa too.

The Mohawk Cabin @ Wigwam Western Summit - North Adams The Mohawk Cabin
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The Mohawk Cabin @ Wigwam Western Summit - North Adams

The Mohawk Cabin offers a studio space for up to two who can look forward to magnificent Mount Gridlock and sunset views. There’s a private trail for hiking, a hammock for a snooze afterward, and a grill for cookouts. It has a bistro table and picnic table for outdoor dining, and when the sun goes down, the perfect place to be is at the fire pit under the stars making S’mores. The nearby Wigwam store can provide picnic baskets for breakfast, lunch, and dinner, with delivery right to your cabin available.

Artsy Pine Cabin in the Woods - Warwick Artsy Pine Cabin
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Artsy Pine Cabin in the Woods - Warwick

Tucked in the woods on a family homestead,  this cozy one-room cabin will immerse you in nature and tranquility. Your artist/hosts have used the space as both a gallery and a rental, with an electric kettle, mini-fridge, and water provided. Just steps away is an outdoor hot shower next to the main house and guests are welcome to use the indoor shower when it’s chilly out. There’s also an outhouse, two hammocks, a fire pit, a Coleman camping stove with cookware, and a picnic table.

'Best of Boston 7/21' 45 ft Yacht - Boston Best of Boston Yacht
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'Best of Boston 7/21' 45 ft Yacht - Boston

While a lot of boat rentals have less than stellar reviews, the “Best of Boston 7/21” is a 45′ yacht with five stars across the board. If you’re looking for a unique stay on the water right in the city, this one is ideal, docked in a secured, gated marina in Boston Harbor. It includes two queen staterooms, each with its own bathroom and shower, plus a sleeper sofa in the salon. You’ll have a microwave, a full fridge, a TV, and access to a community BBQ grill on the docks.

Historic 1693 Mansion - Sandwich Historic 1693 Mansion
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Historic 1693 Mansion - Sandwich

This gorgeous Cape Cod mansion dates back to 1693 as one of the oldest privately owned homes in the country. Called the “Newcomb Tavern,” it was once used for lodging dignitaries during the American Revolution. It includes seven bedrooms, sleeping up to 14, and sits right on Shawme Pond in downtown Sandwich. It has a working grist mill and plenty of modern luxuries, like a professional-grade gourmet kitchen, a fireplace, and a hot tub.

Lakeside Cottage - Ashburnham Lakeside Cottage Breezy Point
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Lakeside Cottage - Ashburnham

Breezy Point is a lakeside cottage with two bedrooms for up to five guests. Here you can look forward to sipping your morning coffee on the deck while watching a beautiful sunrise, made even more spectacular with the serene vision of fog across the water. During the day, take advantage of the complimentary rowboat, canoe, or two single sit-on-top kayaks to get out on the water. There’s a grill for cookouts, a hammock for naps, and gorgeous sunset views too. All the essentials are included inside like free Wi-Fi, cable TV, and a full kitchen.

MV Beach Rose - Martha's Vineyard MV Rose Victorian Cottage
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MV Beach Rose - Martha's Vineyard

This adorable Victorian home is a short stroll from just about everywhere you’ll want to be while on the island of Martha’s Vineyard, including Inkwell Beach, which is just 533 feet away. It sits in the historic Copeland District near eclectic boutiques, eateries, and the ferry, accommodating up to eight in four bedrooms. The wrap-around porch is a highlight, providing the perfect spot to relax, although you’ll have a private back patio with a BBQ area that includes a space for alfresco dining. A full kitchen, family room/living area, and washer/dryer are included too.

Impeccable Cottage Steps to Oak Bluffs - Martha's Vineyard Impeccable cottage steps to downtown
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Impeccable Cottage Steps to Oak Bluffs - Martha's Vineyard

This gingerbread cottage sits among the colorful vintage homes Oak Bluffs is famous for. A stay here will put you just a 5-minute walk to the beach while the restaurants and shops downtown are easily reached on foot too. The home dates to the late 19th-century and includes large Gothic-style windows, wood floors, and vaulted beamed ceilings, with all the modern comforts too. One of the top spots to be is in a rocking chair on the front porch watching the world go by, followed by cooking out on the grill and alfresco dining on the back deck.

Cottage on the River near Providence/Cape Cod/Newport - Somerset Cottage on the River
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Cottage on the River near Providence/Cape Cod/Newport - Somerset

Located on the Taunton River close to the Rhode Island state line, this beautiful bungalow offers water views from many vantage points inside and out. It includes two bedrooms plus a bonus room that’s detached from the house, accommodating up to six guests. It enjoys a quiet setting, yet it’s close to many major attractions, with the Newport mansions just 25 miles away. Look forward to watching sunrises over the river while enjoying all the essentials, including TV with Netflix and Hulu Plus, Wi-Fi, a full kitchen, and a washer/dryer.

A Sweetwater Stay - Orange The Fishing Cottage: A Sweetwater Stay
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A Sweetwater Stay - Orange

The Fishing Cottage offers a “Sweetwater Stay” located on the shores of Tully Pond while providing spectacular views of Tully Mountain in north-central Massachusetts. It has an organic feel, made with real salvaged barn wood walls, up-cycled maple floors, and unique handcrafted furniture. The back deck is the spot to sip your morning coffee and watch sunsets over Tully Mountain, while the master bedroom has a queen-size bed positioned to enjoy the mountain view as well, complete with walls of windows on two sides. A few of the other notable features include the galley kitchen stocked with staples, a washer/dryer, gas fireplace, and a large flat-screen TV with Netflix.

3 Bedroom Luxury Private Home - Boston 3 Bedroom Luxury Private Home
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3 Bedroom Luxury Private Home - Boston

If you want to be right in the city, this three-bedroom home boasts an unbeatable location in a family-friendly neighborhood just a mile from the convention center and less than 10 minutes from the airport. It accommodates up to eight guests and includes lots of luxurious amenities. The beds are ultra-comfy and the kitchen is high-end, with everything you need to whip up gourmet meals. A TV, washer/dryer, and a/c are all included too.

Farm Stay in a Historic Ski Lodge turned Barn - Holden The Farm at SummitWynds
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Farm Stay in a Historic Ski Lodge turned Barn - Holden

This unique rental was originally a ski lodge before being converted into a horse barn, with the hayloft now providing a tranquil farm stay for up to five. A working lavender farm with animals, from April through November, you can even help feed the sheep and get up close to the pigs, horses, and chickens. There are plenty of ways to relax, with a patio for watching sunrises, sunsets, and stargazing. Guests can also enjoy strolling the Lavender Labyrinth and hikes on a one-mile nature walk. Conservation land lies adjacent, providing opportunities for a longer hike, mountain biking, or cross-country skiing.

Waterfront Cottage Escape with Wildlife Sanctuary - Leicester Waterfront Cottage Escape with a Wildlife Sanctuary
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Waterfront Cottage Escape with Wildlife Sanctuary - Leicester

A two-bedroom waterfront cottage for four on Burncoat Pond, here you can enjoy an unforgettable stay that can include boating and all types of watersports. There may be no better way to start the day than by watching the geese and ducks while sipping coffee. The full kitchen includes a coffee maker and Keurig machine along with everything else you’ll need to make your meals. There’s a washer/dryer, Wi-Fi, TV, and even items for the little ones too, like a crib, books, and toys.

Cider House Cottage - Petersham Cider House Cottage
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Cider House Cottage - Petersham

Cider House Cottage is a historic guest cottage on a country farm with forests, fields, ponds, and streams that are ideal for a refreshing dip during the warm summer months. Guests can enjoy miles of scenic hiking and biking right from their door, along with fabulous bird watching. A post and beam home for up to two, it has a terrace with pond views, a clawfoot tub for relaxing soaks, a fireplace, Wi-Fi, and a well-equipped kitchen with a full-size fridge and some cooking basics.

Quiet Country Retreat with Modern Conveniences - Sterling Quiet Country Retreat
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Quiet Country Retreat with Modern Conveniences - Sterling

Enjoy quintessential New England from this spacious farmhouse for up to eight guests. It sits on a 5-acre knoll providing picturesque mountain views, 300 feet from a tranquil country road. While it has a secluded feel with access to parks, hiking, kayaking, and biking, you’ll be close to grocery stores, shops, and eateries. If you can’t tear yourself away from the views, restaurant delivery is available here too.

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