Holiday rentals with outdoor seating in Winthrop

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Winthrop

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

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Guest favourite

Cottage in Winthrop

4.99 out of 5 average rating, 419 reviews

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in a small safe seaside community called Point Shirley. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free wireless Wi-Fi, RokuTV, & one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

12–19 Jul

$329 SGD per night

Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 106 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

22–29 Mar

$136 SGD per night

Guest favourite

Apartment in Winthrop

4.99 out of 5 average rating, 127 reviews

Beachfront Boston: Large, Cozy, Relaxed + Pets

New 2-person soaker tub with ocean-view! Gather with family & friends in this owner-hosted home. Private entrance, entire 1st floor of a multi-family home, with normal family/kid sounds. Pro-cleaned and pet-friendly, space for everyone. Scoot into adjacent Boston by car, ferry/transit, or snuggle-up for a movie on the 70” TV. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all

7–14 Nov

$400 SGD per night

Guest favourite

Guest suite in Winthrop

4.92 out of 5 average rating, 1198 reviews

Licensed Boston airport studio 5 stars, subway

We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.

27 Jul – 3 Aug

$277 SGD per night

Guest favourite

Cabin in Cohasset

4.92 out of 5 average rating, 285 reviews

Lionsgate at Cohasset

Lionsgate is the perfect retreat to refresh the soul. Newly remodeled fully stocked kitchen with comfortable amenities provide a home away from feel. Enjoy a roaring fire in a rustic cabin during the winter or the coolness of a mini split in the summer. Cohasset, jewel of the South Shore is a quintessential New England seaside village located half way between Boston and Cape Cod. The ocean offers abundant recreation opportunities as well as plentiful parks for hiking and biking. A must visit.

7–14 Oct

$212 SGD per night

Superhost

Flat in Revere

4.86 out of 5 average rating, 157 reviews

Stunning Oceanview-4 Train Stop Logan Airport

Stunning 1 bedroom huge apartment with partial ocean views of Revere Beach. This upscale home has it all!! Just one flight up then you enter a hardwood floor foyer, opens to a huge living room with upscale decor, large eat in kitchen stainless steel appliance, country table has seating for 4, tile floor, gas range, and lots of cabinet space, with views of Revere Beach and ocean, giant bathroom complete with tiled shower and stackable laundry (Washer and Dryer) and huge bedroom with closet.

17–24 Nov

$259 SGD per night

Superhost

Home in Revere

4.8 out of 5 average rating, 142 reviews

Renovated Cozy City Getaway

Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.

28 Dec – 4 Jan

$132 SGD per night

Guest favourite

Guest suite in Dover

4.98 out of 5 average rating, 183 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

3–10 Jan

$201 SGD per night

Guest favourite

Flat in Winthrop

4.95 out of 5 average rating, 194 reviews

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Our saltwater pool is nicely terraced and overlooks stunning ocean views. We are 4 short miles from the city and public transportation is easily accessible; a convenient option into Boston. Winthrop is a welcome relief from the hustle and bustle of the city where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

7–14 Feb

$386 SGD per night

Guest favourite

Guest suite in Winthrop

4.95 out of 5 average rating, 801 reviews

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

20–27 Jul

$305 SGD per night

Guest favourite

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.

28 Oct – 4 Nov

$192 SGD per night

Guest favourite

Home in Lynn

4.91 out of 5 average rating, 227 reviews

Clean, spacious In-Law Suite -Near Everything

Immaculately furnished, clean and spacious In-Law Suite features: 1 bedroom, 1 full bath, dining kitchen, and living room located steps from Lynn Woods Reservation (over 30 miles of picturesque New England trails perfect for hiking, running, mountain biking and cross-country skiing) and short drives from beaches, Boston and North Shore. Kids toys, a baby crib and access to a large beautiful upstairs deck and bbq are available upon request.

3–10 Apr

$196 SGD per night