Winthrop, MA Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winthrop

  • Private Rooms, Shared Bath in Cozy Homestay Minutes From Logan Airport
     Family Stay
    Booking.com
    From
    $92
  • King Studio
     Studio
    HolidayLettings
    From
    $255
  • Broadway arms
     Home/Apartment
    Booking.com
    From
    $144
  • Cozy Two Bedrooms near Airport East Boston Basement
     2br Home/Apartment
    HolidayLettings
    From
    $330
  • 2 BR by Boston Harbor & Airport
     Home/Apartment
    Booking.com
    From
    $275
  • 1 minute to T and beach, 15mins to downtown Boston
     4br Home/Apartment
    HolidayLettings
    From
    $512
  • Mirage Luxury Apartments Seaport
     Home/Apartment
    Booking.com
    From
    $299
  • Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $400

Check prices for these upcoming dates

Winthrop Vacation Rentals with a Pool

  • Oceanfront Pool. Close to Boston. Free Parking.
    ExcellentHome/Apartment
    Airbnb
    From
    $232

Winthrop Vacation Rentals with Wi-Fi

  • Casa De Los Clarey Boston Logan Airport Park Free
    Excellent2br Home/Apartment
    Airbnb
    From
    $243
  • Close to Airport, Boston and Revere Beach
    Excellent2br Home/Apartment
    Airbnb
    From
    $212
  • Family friendly 2BR 5mins to Boston w st parking
    Excellent2br Home/Apartment
    Airbnb
    From
    $167
  • Beachside Cozy Space-Near Boston/Airport/Train
    ExcellentHome/Apartment
    Airbnb
    From
    $147

Winthrop Pet-Friendly Vacation Rentals

  • Houseboat in Boston Harbor
    GoodBoat
    Flipkey
    From
    $546
  • Hillcrest Cottage By The Sea
    Good3br Home/Apartment
    HolidayLettings
    From
    $384
  • Rodri and Wandy's Place
     3br Home/Apartment
    HolidayLettings
    From
    $368
  • Sweet studio 15 minutes from Bos.Logan Airport. 10 miles to downtown crossing.
     -1br Studio
    HolidayLettings
    From
    $122

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
65° 10°
3
70° 15°
3
77° 30°
7
89° 43°
3
87° 53°
5
98° 63°
6
95° 57°
3
92° 50°
2
81° 42°
4
72° 21°
3
63° 15°
6
59°
4
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Winthrop. The warmest months in Winthrop are June and May, when temperatures reach 98 ˚F. The coolest month is December, when temperatures drop to 5 ˚F. The wettest month in Winthrop is September with 6.52 inches of rain, while the driest month is April with 2.16 inches of rain.

What Expert Travelers Think

  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels

Vacation Rentals in Winthrop

At AllTheRooms.com we have rentals from all of the best providers - Airbnb, Priceline, Agoda and more. We have 126 vacation rentals, hotels and other accommodation types in Winthrop ranging from low-cost options to extravagant places to stay. For those wanting to save money, the lowest priced place to stay in Winthrop comes in at $10 a night. The average price of an accommodation is $145 per night.

If you want internet access during your stay in Winthrop, then you can choose from over 68 accommodations that provide WiFi internet. 11 places to stay include a morning meal. Fitness addicts can get a workout in during their stay by choosing from 3 accommodations that have gym facilities. If you're planning on getting to Winthrop by car, be sure to choose from 55 accommodations that provide parking. We have 4 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 9 pet-friendly places to stay in Winthrop, so if you're traveling with your pet you won't have any problems.

78 accommodations in Winthrop have been reviewed; 84% are rated highly. You can instantly book any of 38 places to stay right now.

Destinations near Winthrop

  • Boston3,430 Properties
  • Nantucket3,184 Properties
  • Provincetown2,222 Properties
  • Dennis Port1,605 Properties
  • Eastham1,537 Properties
  • Chatham1,425 Properties
  • Brewster1,323 Properties
  • Wellfleet1,240 Properties
  • Orleans1,158 Properties
  • Oak Bluffs1,114 Properties
  • Somerville1,009 Properties
  • Edgartown979 Properties
  • West Yarmouth899 Properties
  • Cambridge865 Properties
  • Falmouth858 Properties
  • Mashpee840 Properties
  • Hyannis792 Properties
  • South Yarmouth762 Properties
  • Brookline747 Properties
  • Tisbury699 Properties
  • Plymouth666 Properties
  • Rockport655 Properties
  • East Falmouth650 Properties
  • West Dennis616 Properties
  • North Truro584 Properties
  • Gloucester574 Properties
  • South Chatham568 Properties
  • Lenox533 Properties
  • Harwich501 Properties
  • Worcester482 Properties
  • Salem460 Properties
  • Dennis453 Properties
  • Harwich Port440 Properties
  • East Sandwich435 Properties
  • Centerville431 Properties
  • Hancock425 Properties
  • Great Barrington403 Properties
  • Revere393 Properties
  • Vineyard Haven393 Properties
  • Waltham379 Properties
  • Lee358 Properties
  • Northampton352 Properties
  • Sandwich337 Properties
  • Quincy337 Properties
  • Truro335 Properties
  • Newton327 Properties
  • Medford318 Properties
  • Watertown316 Properties
  • Williamstown312 Properties
  • Newburyport305 Properties
  • Marblehead297 Properties
  • Pittsfield297 Properties
  • South Dennis280 Properties
  • North Falmouth262 Properties
  • Chelsea260 Properties
  • Amherst252 Properties
  • Marshfield242 Properties
  • Stockbridge239 Properties
  • Arlington229 Properties
  • Osterville228 Properties
  • Barnstable226 Properties
  • Wareham204 Properties
  • Scituate196 Properties
  • West Harwich191 Properties
  • Woburn185 Properties
  • Chilmark166 Properties
  • Bourne161 Properties
  • Sturbridge150 Properties
  • Fairhaven134 Properties
  • Ipswich116 Properties
  • Westport115 Properties
  • West Stockbridge108 Properties
  • Marlborough107 Properties
  • Hull95 Properties
  • New Marlborough87 Properties
  • Sheffield80 Properties
  • Manchester75 Properties
  • Springfield64 Properties
  • Concord63 Properties
  • Sudbury48 Properties
  • Ashburnham33 Properties
  • Cheshire22 Properties
  • Hubbardston8 Properties