Vacation rentals with outdoor seating in Massachusetts

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Top-rated outdoor seating rentals in Massachusetts

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Farm stay in Southbridge

4.89 out of 5 average rating, 316 reviews

Scandanavian Wigwam with Sauna and Forest Baths

Deep sleeps await in our off grid forest Wigam. With everything you need, and nothing you do not, this exceptional retreat boasts a Danish Morso wood stove, fire pit, private forest baths, Finnish sauna, HUGE windows overlooking a wildlife trail and Peepers Owls and Coyote song. From photo shoots to wedding proposals - this is a special place to care for yourself and your family. We are on farm - but out of sight. Bring your kids, dogs, friends, guitar, or just a good book and settle in!

Guest favorite

Guest suite in Winchester

5 out of 5 average rating, 160 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 377 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 175 reviews

Cider House Cottage

Antique guest cottage on a country farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub.

Guest favorite

Tiny home in Wellfleet

4.98 out of 5 average rating, 280 reviews

Writer's Cabin in Woods near Wellfleet Bay

Our unique, creative and magical "Writer's Cabin" tiny house is a guest favorite! You'll be tucked in the woods with the views of a treehouse, and just minutes' drive or bike ride to Wellfleet's beaches, ponds & walking trails. Wellfleet's quaint town center and harbor are just a 10-15 minutes walk down the road. Note: the cabin has a private, wooden Nordic shower w/ hot water built onto the outside of the cabin. Our guests love this unique experience! The toilet is standard flushing & indoors.

Guest favorite

Cottage in Sandwich

4.95 out of 5 average rating, 202 reviews

Lakefront cottage, private Beachfront, Wow View!

Wake up to a magnificent view of a beautiful lake with waves lapping below your window! See video tour on YouTube. Search: "Cape Cod Lakefront Vacation Retreat. Panorama View". Guests love this stylish and open cottage located on the shore of a large, recreational lake. It's like being on your own luxury houseboat! Wall-to-wall windows with panoramic views, private beach, new modern kitchen, luxurious King gel/coil bed, private office space, large bathroom with curved shower, and much more!

Guest favorite

Cottage in Plymouth

4.94 out of 5 average rating, 265 reviews

Ocean View Cottage

Charming cottage with an ocean view in a private setting seaside community with updated kitchen that does NOT include a stove however there is a cooktop, microwave and toaster oven, 3/4 bathroom w a shower. Firestick/RokuTV. It is ONE room, open concept with a comfortable memory foam easy fold out king couch. The cottage is separate from the house and has its own entrance w own parking for 2 cars. 1 mile from the beach and 5 miles from downtown. **PLEASE NOTE ONLY 2 PERSON OCCUPANCY**!!

Guest favorite

Guest suite in Uxbridge

4.99 out of 5 average rating, 191 reviews

Zen Inspired Private Suite with 2-mile Trail Loop

Zig-Zag Trails unique offering is a harmonious blend of modern comfort and the timeless allure of rural living. A newly built 1000 sq ft guest suite situated on over 65 acres of private meadows and forests with zig-zagging trails throughout, providing the ultimate getaway to relax and recharge. This property is a haven for nature lovers and homebodies alike. We are conveniently located in the heart of the Blackstone Valley, 1hr from Boston, 35min from Providence, and 25min from Worcester.

Guest favorite

Guest suite in Concord

4.97 out of 5 average rating, 114 reviews

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Guest favorite

Barn in Holden

4.9 out of 5 average rating, 422 reviews

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Guest favorite

Tiny home in Orange

4.92 out of 5 average rating, 344 reviews

The Writer's Retreat: A Sweetwater Stay

Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.

Guest favorite

Guest suite in Rockport

4.98 out of 5 average rating, 660 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.