Winthrop, MA Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winthrop

  • New 3bd Apt Walk to Airport/T Mins to DWTN/Casino
     Home/Apartment
    Booking.com
    From
    $138
  • King Studio
     Studio
    HolidayLettings
    From
    $248
  • Broadway arms
     Home/Apartment
    Booking.com
    From
    $104
  • Cozy Two Bedrooms near Airport East Boston Basement
     2br Home/Apartment
    HolidayLettings
    From
    $330
  • Clean Comfy Centrally Located Private Room
     Family Stay
    Booking.com
    From
    $71
  • 1 minute to T and beach, 15mins to downtown Boston
     4br Home/Apartment
    HolidayLettings
    From
    $512
  • Seaport Suites
     Home/Apartment
    Booking.com
    From
    $199
  • East Boston | 2bd/2ba | New Construction with Parking!
     2br Home/Apartment
    HolidayLettings
    From
    $336

Check prices for these upcoming dates

Winthrop Vacation Rentals with Wi-Fi

  • Licensed Boston airport suite 5 stars, subway
    ExcellentHome/Apartment
    Airbnb
    From
    $102
  • Boston Home mins to airport/Walk to T-Line & beach
    Excellent3br Home/Apartment
    Airbnb
    From
    $263
  • Modern apartment by Logan Airport
    ExcellentHome/Apartment
    Airbnb
    From
    $169
  • Family friendly 2BR 5mins to Boston w st parking
    Excellent2br Home/Apartment
    Airbnb
    From
    $148

Winthrop Pet-Friendly Vacation Rentals

  • Hillcrest Cottage By The Sea
    Good3br Home/Apartment
    HolidayLettings
    From
    $372
  • Rodri and Wandy's Place
     3br Home/Apartment
    HolidayLettings
    From
    $336
  • Sweet studio 15 minutes from Bos.Logan Airport. 10 miles to downtown crossing.
     -1br Studio
    HolidayLettings
    From
    $116
  • Modern Studio By With Kendall Harvard
     -1br Studio
    HolidayLettings
    From
    $256

Winthrop Travel Guide

Winthrop, Massachusetts, is a small city best known for its proximity to nice parks and beaches in the surrounding area in Boston.

Things to Do in Winthrop

Top things to do in Winthrop include exploring the nearby Boston Harbor Islands National Recreation Area, where you can find out more about the history of the area, and take a dip in the sea at the nearby Constitution Beach.

Best Time to Visit Winthrop

The best time to visit Winthrop is in the summer months of July and August when the weather is hot and sunny.

Cabins in Winthrop

The small town of Winthrop Massachusetts is located in the perfect position near to the bustling town of Boston, but far enough away to feel as though you have escaped busy city life. Winthrop is also located near the Boston Harbour Islands National Recreation Area which is a beautiful place for a day trip. If you are more of a beach lover, head to Constitution Beach for a little TLC in the sun and dip in the crystal clear waters of the sea. On the coastline you may just be able to see Nix’s Mate, a daybeacon pyramid, which is all that is left of an island said to have sunk due to a pirate's curse.

Many people who are looking to explore Boston will get a Winthrop cabin rental, which come in a range of sizes to suit different party sizes and budgets.

Price and Availability in Winthrop

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Winthrop tends to be Wednesday, while the most expensive day tends to be Friday. Vacation homes in Winthrop tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Winthrop is in August, while the cheapest month is in January. The most popular time to book a vacation rental in Winthrop is in the high season in October. Winthrop has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Winthrop

Rainy days
70° 14°
9
65° 20°
3
61° -2°
5
72° 10°
4
64° 16°
5
70° 29°
5
90° 44°
2
92° 49°
3
98° 61°
5
98° 62°
5
97° 53°
5
86° 34°
4
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Winthrop. The hottest month in Winthrop is May, when temperatures peak at 98 ˚F. The coolest month is December, when temperatures drop to -2 ˚F. The wettest month in Winthrop is February with 9.26 inches of rain, while the driest month is August with 1.9 inches of rain.

What Expert Travelers Think

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  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

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Vacation Rentals in Winthrop

Browse vacation rentals from all the leading providers including Airbnb, Priceline, Agoda and many more at AllTheRooms.com. AllTheRooms has 136 rentals, hotels and other great places to stay during your time in Winthrop, with everything from budget hostels and homestays to extravagant Airbnbs and hotels. For those traveling on a budget, the most economical place to stay in Winthrop is available at $28 per night. The average price of a vacation rental is generally $153 per night.

If you need to stay connected during your trip, then you can choose from over 65 accommodations in Winthrop that have WiFi. We have 11 accommodations that come with breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 3 accommodations that have gyms. If you're planning on getting to Winthrop by car, be sure to choose from 51 accommodations that provide parking. We have 4 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 6 pet-friendly places to stay in Winthrop, so if you're traveling with your cat or dog you won't have any problems.

76 accommodations in Winthrop have been reviewed; 79% are rated highly. 43 accommodations allow instant booking.

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