Winthrop, MA Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winthrop

  • 2 BEDROOM CLOSE TO BEACH/BOSTON/TD GARDEN/DOWNTOWN
    ExcellentCountry House
    Booking.com
    From
    $221
  • King Studio
     Studio
    HolidayLettings
    From
    $242
  • Perkins Inn
     Home/Apartment
    NextTrip
    From
    $243
  • BOSTON AIRBNB SAVE $$$ ON STAY #1A
    NiceHome/Apartment
    Booking.com
    From
    $126
  • 1 minute to T and beach, 15mins to downtown Boston
     4br Home/Apartment
    HolidayLettings
    From
    $480
  • Two-Bedroom in North End
    GoodHome/Apartment
    Booking.com
    From
    $351
  • Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $400
  • The Fort Residences by Barsala
     Home/Apartment
    Booking.com
    From
    $432

Check prices for these upcoming dates

Winthrop Vacation Rentals with a Pool

  • Oceanfront Pool. Close to Boston. Free Parking.
    ExcellentHome/Apartment
    Airbnb
    From
    $259

Winthrop Vacation Rentals with Wi-Fi

  • Pleasant Place 2 -Boston/Logan Airport/Winthrop
    Excellent2br Home/Apartment
    Airbnb
    From
    $215
  • Oceanview Unit 2R for 10 mins to Boston /airport
    Good2br Home/Apartment
    Airbnb
    From
    $180
  • Spacious 1 Bed Apartment (close to Logan Airport)
     Home/Apartment
    Airbnb
    From
    $124
  • Seaside basement studio
    NiceHome/Apartment
    Airbnb
    From
    $175

Winthrop Pet-Friendly Vacation Rentals

  • Houseboat in Boston Harbor
    GoodBoat
    Flipkey
    From
    $546
  • Rodri and Wandy's Place
     3br Home/Apartment
    HolidayLettings
    From
    $304
  • Modern Studio By With Kendall Harvard
     -1br Studio
    HolidayLettings
    From
    $256
  • Historic Brownstone
     Home/Apartment
    HolidayLettings
    From
    $540

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
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
97 º53
5
86 º34
4
70 º14
9
65 º20
3
61 º-2
5
72 º10
4
64 º16
5
70 º29
5
90 º44
2
92 º49
3
98 º61
5
98 º62
5
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Winthrop. The warmest months in Winthrop are May and June, when temperatures reach 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

  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

    Monica
    MonicaNYCTechMommy
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker

Vacation Rentals in Winthrop

At AllTheRooms.com we have rentals from all of the leading providers - Airbnb, Priceline, Agoda and many more. We have 122 vacation rentals, hotels and other places to stay in Winthrop ranging from cheap options to luxury places to stay. For those trying to save money, the cheapest place to stay in Winthrop is only $30 per night. An average accommodation in Winthrop costs on average $161 a night.

Those looking to get some work finished during their trip to Winthrop can pick from 60 places to stay that provide WiFi. 10 of our accommodations come with breakfast in the price. If you're planning on getting to Winthrop by car, be sure to choose from 47 accommodations that provide parking. We have 4 vacation rentals that have a pool or jacuzzi.

If you're traveling with your best friend, then be sure to select one of the 5 pet-friendly accommodations available.

74 of our rentals in Winthrop have been rated by previous guests. They rated 78% as great. You can instantly book any of 43 places to stay right now.

Destinations near Winthrop

  • Boston4,334 Properties
  • Nantucket3,133 Properties
  • Provincetown2,336 Properties
  • Eastham1,535 Properties
  • Dennis Port1,501 Properties
  • Brewster1,413 Properties
  • Chatham1,340 Properties
  • Wellfleet1,273 Properties
  • Orleans1,221 Properties
  • Oak Bluffs1,153 Properties
  • Somerville1,114 Properties
  • Edgartown998 Properties
  • Cambridge997 Properties
  • West Yarmouth963 Properties
  • Falmouth927 Properties
  • Hyannis892 Properties
  • Mashpee885 Properties
  • Brookline847 Properties
  • Rockport781 Properties
  • Tisbury758 Properties
  • South Yarmouth752 Properties
  • East Falmouth679 Properties
  • Plymouth675 Properties
  • Gloucester649 Properties
  • South Chatham592 Properties
  • North Truro574 Properties
  • Dennis538 Properties
  • Lenox536 Properties
  • West Dennis522 Properties
  • Harwich518 Properties
  • Worcester505 Properties
  • Centerville496 Properties
  • East Sandwich467 Properties
  • Salem463 Properties
  • Harwich Port444 Properties
  • Waltham438 Properties
  • Great Barrington437 Properties
  • Hancock411 Properties
  • Lee407 Properties
  • Northampton394 Properties
  • Newton387 Properties
  • Vineyard Haven384 Properties
  • Revere354 Properties
  • Sandwich350 Properties
  • Williamstown345 Properties
  • Newburyport342 Properties
  • Quincy341 Properties
  • Medford341 Properties
  • Truro340 Properties
  • North Falmouth338 Properties
  • Watertown322 Properties
  • Pittsfield309 Properties
  • Marblehead307 Properties
  • Amherst265 Properties
  • Chelsea264 Properties
  • Marshfield258 Properties
  • South Dennis255 Properties
  • Stockbridge255 Properties
  • Arlington245 Properties
  • Osterville232 Properties
  • Barnstable231 Properties
  • Woburn224 Properties
  • Scituate212 Properties
  • West Harwich203 Properties
  • Wareham202 Properties
  • Sturbridge190 Properties
  • Bourne180 Properties
  • Chilmark174 Properties
  • Marlborough152 Properties
  • Fairhaven132 Properties
  • Westport121 Properties
  • Ipswich117 Properties
  • West Stockbridge116 Properties
  • Hull110 Properties
  • Sheffield84 Properties
  • Manchester83 Properties
  • New Marlborough81 Properties
  • Concord80 Properties
  • Springfield67 Properties
  • Sudbury52 Properties
  • Ashburnham34 Properties
  • Cheshire27 Properties
  • Hubbardston8 Properties