Going on the same types of dates can become mundane. If you've found yourself yawning over the idea of yet another Friday night dinner and a movie with your S/O, there's a solution. Finding new and exciting date ideas in Massachusetts isn't always easy, but Airbnb can help you spruce it up a bit.


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It might be time to think outside the box and take it up a notch with a weekend getaway. Thanks to these unique and intimate accommodations, you can skip dinner and movie and opt for a fun retreat to one of these romantic and affordable destinations that are just a car ride away.

The Pondhouse

Price: $265 per night

Neighborhood: Ashfield

Sleeps: 3

Why You Should Go: Get lost in a true glamping experience with this cozy, rustic cabin. You can take in nature without leaving your cozy bed through the transparent screen walls. This woodsy retreat includes an outdoor shower and firepit with no cell or internet service, so it's the perfect place to unplug and rejuvenate. 

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Octagonal Treehouse

Price: $269 per night

Neighborhood: Otis

Sleeps: 4

Why You Should Go: This unique concept includes floor to ceiling windows that allow you to gaze out onto the seven private acres surrounding the property. You can take advantage of the massive back deck equipped with a grill and lots of seating for you and your guests. You can also warm up indoors with the modern wood-burning fireplace in the center of the living space. 

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Farm House

Price: $157 per night

Neighborhood: Westhampton

Sleeps: 6

Why You Should Go: This modern, renovated farmhouse is the perfect outdoor escape. You and your boo can relax and share drinks in the outdoor hot tub and share a romantic dinner cooked on the grill. Chill on the huge deck and enjoy the sounds of nature or play games like croquet and badminton.

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Fairytale Silo Suite

Price: $257 per night

Neighborhood: Tyringham

Sleeps: 4

Why You Should Go: This former sculptor studio has been transformed into a magical, rustic lodge. Get playful with your S/O in the game room and reignite the romance by snuggling up on the fairytale bed with a canopy. With one-of-a-kind decor and architecture, plus all the amenities you need, you may never want to leave.

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Romantic Oceanview Suite

Price: $199+ per night

Neighborhood: Swampscott

Sleeps: 2

Why You Should Go: You can ogle over fantastic ocean views from each and every window at this bungalow near Boston. You and your bae can have some fun cooking together in the fully-renovated chef's kitchen, spice up the night in the private outdoor spa and indoor jacuzzi, snuggle up by the fireplace and look at the stars from the wrap-around deck.

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Romantic Treehouse Retreat

Price: $208+ per night

Neighborhood: Provincetown

Sleeps: 2

Why You Should Go: This two-bedroom couples retreat in the trees has everything you need for a romantic getaway. Enjoy water views, a unique hot tub on the deck and a magical electric fireplace. You're a short walk away from sandy beaches, shops and restaurants if you want to venture out for a date night on the town.

Martha's Vineyard Guest House

Price: $265 per night

Neighborhood: Chilmark

Sleeps: 2

Why You Should Go: On this private guest house beaming with sunlight, there are gorgeous views of surrounding nature on the iconic Martha's Vineyard. The cozy, intimate bedroom, outdoor shower and secluded wooden deck are perfect for reconnecting with your sweetheart.

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Enchanting Loft Cottage

Price: $130+ per night

Neighborhood: Barnstable

Sleeps: 2

Why You Should Go: This modern, nautical cottage offers vaulted ceilings and a lofted bedroom connected by a ship ladder-style staircase. Enjoy the blue skies and cocktails on the deck of this cozy, Cape Cod escape.

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Historic Oceanfront Apartment

Price: $136+ per night

Neighborhood: Salem

Sleeps: 2

Why You Should Go: Right on the water, let the sound of crashing waves lull you to sleep or enjoy a glass of wine as you sit out in the yard overlooking the water. Recently renovated, you and your date can enjoy a fully-equipped kitchen, a bathroom with heated floors and a cutesy bedroom with comfy chairs.

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Treehouse Farm Stay

Price: $125+ per night

Neighborhood: Rehoboth

Sleeps: 4

Why You Should Go: This off-the-grid treehouse overlooks vast farm fields to the south and forest to the north. Composting toilet close by. There's a cozy wood stove, a spacious outdoor shower and lanterns for a truly romantic vibe.

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Waterfront on Gull Pond

Price: $350 per night

Neighborhood: Wellfleet

Sleeps: 4

Why You Should Go: You can enjoy a private beach on Gull Pond in the protected Cape Cod National Seashore at this zen escape. Take in the magnificent views from the waterfront deck, get cozy after sunset in the massive enclosed porch and rinse off in the outdoor heated shower.

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Cozy Cabin in the Berkshires

Price: $157 per night

Neighborhood: Otis

Sleeps: 4

Why You Should Go: This spacious abode is equipped with an open floor plan with high ceilings and a lofted sleeping area. You can find food from local farms and whip up something tasty in the full kitchen complete with a wood stove. For tons of pictures from satisfied guests, check out the cabin's Instagram account @otiscabin.

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Hiker's Hideaway

Price: $107 per night

Neighborhood: Easthampton

Sleeps: 6

Why You Should Go: You can take full advantage of some of the best hiking spots in New England at this private escape nestled at the foot of Mt. Tom. After working up a sweat, you can get cozy in the canopy bed, watch some flicks in the home theatre or curl up with a good book from the massive library.

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Wings Neck Lighthouse

Price: $540+ per night

Neighborhood: Pocasset

Sleeps: 8

Why You Should Go: This unique historic accommodation was once a U.S. Coast Guard lighthouse. You'll have access to incredible, panoramic views of the Atlantic and a peaceful private beach. There are also lots of additional must-see beaches on the Cape nearby.

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These prices and terms of occupancy are confirmed at the time of publishing, but they can change at any time.

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