Vacation rentals in Winthrop

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Top-rated vacation rentals in Winthrop

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Apartment in Winthrop

4.96 out of 5 average rating, 275 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Mar. 1 – 8

$330 CAD per night

Guest favourite

Cottage in Winthrop

4.99 out of 5 average rating, 418 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.

May 21 – 28

$352 CAD per night

Guest favourite

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

Dec. 29 – Jan. 5

$171 CAD per night

Guest favourite

Condo in Winthrop

4.99 out of 5 average rating, 125 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

Dec. 13 – 20

$447 CAD per night

Guest favourite

Guest suite in Winthrop

4.92 out of 5 average rating, 1194 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.

Oct. 25 – Nov. 1

$320 CAD per night

Guest favourite

Guest suite in Revere

4.92 out of 5 average rating, 199 reviews

Private Studio 10 min from airport

Private guest suite is centrally-located for easy access to the city. Professionally cleaned. You’ll have a private entrance to come and go as you’d like with a code keypad door. Our newly renovated BASEMENT 500 sq ft is perfect for a guests to escape for a few days. Private bathroom and kitchenette, 10 min away from airport. Bus and train station walking distance. 15 min walk to Revere Beach We are in close proximity to Downtown Boston as well as Salem and other areas. Free wifi Street parking

Mar. 20 – 27

$210 CAD per night

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 265 reviews

Private 1BR Pied-a-terre

Fully furnished mini-suite with private entrance; walk in at ground level. Picture window view of, and use of, large back yard. Separate sitting and sleeping areas (full size bed), desk/workspace, bathroom with shower, kitchenette with small fridge, coffeemaker and microwave (no stove). Great take-out nearby. No pets, no smoking permitted. Car? There is off-street covered parkling. No car? 71 Bus to Harvard Square stops at our corner; short walk to other buses and public transportation.

Dec. 5 – 12

$149 CAD per night

Superhost

Home in Revere

4.79 out of 5 average rating, 139 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.

Jan. 24 – 31

$165 CAD per night

Guest favourite

Guest suite in Nahant

4.98 out of 5 average rating, 339 reviews

The Annex Oceanfront

The Annex is the walk-in cellar apartment of a private home, with neighboring houses close-by. It has its own entrance, with a cemented patio which is part of the seawall. My daughter and I share the house, so it is owner-occupied...along with her dog, Luigi. Although there isn't a stove in the unit, there is a neighborhood restaurant. We are located 30 minutes from Boston. Off street parking is available for one car only. Prices are based on 2 guests. Minimum stay is four nights.

Feb. 17 – 24

$239 CAD per night

Guest favourite

Apartment 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.

Jun. 24 – Jul. 1

$534 CAD per night

Guest favourite

Guest suite in Winthrop

4.95 out of 5 average rating, 795 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.

Jun. 11 – 18

$266 CAD 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.

Aug. 9 – 16

$187 CAD per night