Vacation rentals with outdoor seating in Massachusetts

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Top-rated outdoor seating rentals in Massachusetts

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Guest favorite

Guest suite in Tyngsborough

4.98 out of 5 average rating, 216 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Guests can enjoy our home's private suite on a lovely small lake with a panoramic view, a spa-like bathroom, cotton linens, and a comfy bed. A/C and a fireplaced living room. Quietly watch lake nature or boats going by, or venture out to swim, kayak, or fish. Enjoy Lowell's mill history and it's national park, take a forest walk nearby, or drive 10 min. to Nashua, NH for its many restaurants and tax-free shopping. 1 hr from Boston and central to New England highlights. Low cleaning fees!

Aug 2 – 9

G$26,067 GYD per night

Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 104 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

Jan 14 – 21

G$21,002 GYD per night

Guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 150 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.

Oct 27 – Nov 3

G$29,014 GYD per night

Guest favorite

Bungalow in Dartmouth

4.95 out of 5 average rating, 145 reviews

Updated Vintage Bungalow with Incredible Views

This space has been fully updated in the spring of 2020. Incredible unobstructed panoramic views. It is 400 sq' with an additional 350 sq ' of living space on the deck. The neighborhood is quiet, but you are a stones throw from I-195, making places like Boston, Providence and the Cape and Islands very easy to get to. The décor is bright and funky! Close to UMASS. Extensive custom area and house guide is at the Bungalow with everything you need to know to maximize your experience in the area!

Apr 7 – 14

G$32,283 GYD per night

Guest favorite

Guesthouse in Uxbridge

5.0 out of 5 average rating, 124 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.

Apr 4 – 11

G$33,676 GYD per night

Guest favorite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette and an outdoor space with a fire pit and charcoal grill. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

Aug 12 – 19

G$24,869 GYD per night

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a sought after cape style cottage community. It offers a pristine private association beach. The cottage has water views from both the living room and deck. Grab the provided beach chairs, cooler and walk a 140 steps from the deck to the beach. You can also Walk, Bike, or Fish on Cape Cod Canal. Close to restaurants, hiking trails and Mass Maritime. Cape Cod Bridge- 5 min.

Apr 17 – 24

G$28,294 GYD per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 150 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

Apr 8 – 15

G$19,997 GYD per night

Guest favorite

Barn in Holden

4.9 out of 5 average rating, 379 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 through our Lavender Labyrinth and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Jul 18 – 25

G$35,373 GYD per night

Guest favorite

Cottage in Orange

4.94 out of 5 average rating, 131 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

Mar 18 – 25

G$25,087 GYD per night

Guest favorite

Tiny home in Orange

4.92 out of 5 average rating, 310 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.

Mar 21 – 28

G$28,213 GYD per night

Guest favorite

Guest suite in Rockport

4.99 out of 5 average rating, 611 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.

Feb 12 – 19

G$26,224 GYD per night