Winthrop, MA Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winthrop

Studio Near Downtown Boston | Coworking + Free Wi-Fi

RedAwningFrom $342
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Global Luxury Suites at Seaport
Nice
Booking.comFrom $264
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King Studio

HolidayLettingsFrom $257
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Boston Omni Parker House Hotel

NextTripFrom $388
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Conspire Coworking + Fitness Center Access | Unique Studio

RedAwningFrom $406
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Three-Bedroom Apt in the North End
Good
Booking.comFrom $645
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Oceanfront with Salt Water Pool. Close to Boston.

HolidayLettingsFrom $311
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Oasis Guest House

NextTripFrom $335
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Winthrop Vacation Rentals with a Pool

Homewood Suites By Hilton Boston-Peabody

NextTripFrom $234
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Boston Omni Parker House Hotel

NextTripFrom $357
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Comfort ,Large Apartment/Airport/Downtown/TDgarden

AirbnbFrom $239
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Winthrop Vacation Rentals with Wi-Fi

Accessible Loft | Conspire Coworking + Fitness Center Access

RedAwningFrom $406
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Casa de los Clarey Boston Logan Airport Beaches
Excellent
AirbnbFrom $247
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Cozy apartment by the beach
Good
AirbnbFrom $215
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Private clean Walk to Ocean on main Boston Subway
Excellent
AirbnbFrom $221
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Winthrop Pet-Friendly Vacation Rentals

Rodri and Wandy's Place

HolidayLettingsFrom $345
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Luxury 2 Bedroom 2 Bath Apartment Fenway Park Boston

HolidayLettingsFrom $702
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BOSTON LOFT/2BED By Logan Airport&Train 1st Floor
Excellent
AirbnbFrom $495
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Charming renovate2brclose to Boston
Good
AirbnbFrom $248
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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

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

SEE FULL WEATHER FORECAST:

90º 44º

1.9

92º 49º

2.96

98º 61º

4.55

98º 62º

4.65

97º 53º

5.12

86º 34º

3.78

70º 14º

9.26

65º 20º

2.72

61º -2º

4.92

72º 10º

3.77

64º 16º

5.07

70º 29º

4.62

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

Rainy days

SEE FULL WEATHER FORECAST:

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

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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.