We use cookies to provide you with the best browsing experience. The data collected by cookies is used to optimise the website for our users and deliver an appropriate service and relevant information to you. By using our site we assume you’re aware and agree to use the cookies for this purpose.

Destination Photo

Winthrop, MA Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winthrop

See all 117 vacation rentals in Winthrop

Winthrop Vacation Rentals with a Pool

See all vacation rentals in Winthrop with a pool

Winthrop Vacation Rentals with Wi-Fi

See all vacation rentals in Winthrop with WiFis

Winthrop Pet-Friendly Vacation Rentals

See all vacation rentals in Winthrop that allow pets

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 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 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 Weather in Winthrop

90º 44º
92º 49º
98º 61º
98º 62º
97º 53º
86º 34º
70º 14º
65º 20º
61º -2º
72º 10º
64º 16º
70º 29º
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 January, when temperatures drop to -2 ˚F. The wettest month in Winthrop is November with 9.26 inches of rain, while the driest month is May with 1.9 inches of rain.

What Expert Travelers Think

Vacation Rentals in Winthrop

Find the perfect rental for your trip at AllTheRooms.com. We aggregate Airbnb, VRBO, priceline and others. We have 117 vacation rentals, hotels and other places to stay in Winthrop ranging from inexpensive options to luxury places to stay. A trip to Winthrop can be affordable - the lowest price accommodation is available at $30 per night. On average, an accommodation in Winthrop will cost you $158 per night.

If you want an internet connection during your stay in Winthrop, then you can choose from over 52 accommodations that have WiFi internet. 7 of our accommodations include a breakfast in the price. If you are driving to Winthrop, you'll want to pick from 40 places to stay that provide parking. 4 vacation rentals come with a pool or jacuzzi

AllTheRooms has 4 pet-friendly places to stay in Winthrop, so if you're traveling with your cat or dog you won't have any trouble.

69 of our rentals in Winthrop have been reviewed by previous guests. They rated 81% as excellent or good. 37 places to stay in are instantly bookable.

Destinations near Winthrop