Winthrop Vacation Rentals

Compare 243 available properties from 19 providers
Winthrop

Compare and find the perfect property for as little as $39 per night by searching among the 243 properties available in Winthrop. HomeToGo, a vacation rental search engine, directly sorts all of these vacation rentals so you can save up to 10%!

Recommended Vacation Rentals in Winthrop

Rent a vacation accommodation in Winthrop: from $39 per night

House ∙ 2 guests
Winthrop, Suffolk County, Massachusetts, United States
from $65
Homestay.com
5.0
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House ∙ 2 guests
Winthrop, Suffolk County, Massachusetts, United States
from $65
Homestay.com
5.0
View deal
House ∙ 2 guests
Winthrop, Suffolk County, Massachusetts, United States
from $65
Homestay.com
5.0
View deal
House ∙ 2 guests
Winthrop, Suffolk County, Massachusetts, United States
from $65
Homestay.com
5.0
View deal
Apartment ∙ 3 guests ∙ 1 bedroom
Harbor View / Orient Heights, Boston, Massachusetts, United States
from $157
VRBO
4.5
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Apartment ∙ 2 guests
Winthrop, Suffolk County, Massachusetts, United States
from $34
Homestay.com
5.0
View deal
Apartment ∙ 6 guests ∙ 2 bedrooms
East Boston, Boston, Massachusetts, United States
from $225
VRBO
4.8
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Apartment ∙ 2 guests ∙ 1 bedroom
Jeffries Point, Boston, Massachusetts, United States
Check rates
VRBO
4.5
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House ∙ 4 guests ∙ 2 bedrooms
Jeffries Point, Boston, Massachusetts, United States
from $262
VRBO
4.7
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Dog-Friendly Vacation Rentals

Pet-friendly
Apartment ∙ 5 guests ∙ 2 bedrooms
Central-Maverick Square / Paris Street, Boston, Massachusetts, United States
from $102
VRBO
4.7
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Pet-friendly
Apartment ∙ 6 guests ∙ 3 bedrooms
Central-Maverick Square / Paris Street, Boston, Massachusetts, United States
from $275
VRBO
4.5
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Pet-friendly
Apartment ∙ 6 guests ∙ 2 bedrooms
Central-Maverick Square / Paris Street, Boston, Massachusetts, United States
from $277
VRBO
4.7
View deal
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Apartments With Balconies or Patios

Balcony/Patio
Apartment ∙ 3 guests ∙ 1 bedroom
Harbor View / Orient Heights, Boston, Massachusetts, United States
from $55
VRBO
4.5
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Balcony/Patio
Apartment ∙ 4 guests ∙ 2 bedrooms
Revere, Suffolk County, Massachusetts, United States
from $138
VRBO
5.0
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Balcony/Patio
Apartment ∙ 6 guests ∙ 3 bedrooms
East Boston, Boston, Massachusetts, United States
from $260
VRBO
4.9
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Vacation Homes With Fishing Spots Nearby

Fishing
Apartment ∙ 3 guests ∙ 1 bedroom
Harbor View / Orient Heights, Boston, Massachusetts, United States
from $54
VRBO
4.5
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Fishing
House ∙ 6 guests ∙ 3 bedrooms
Revere, Suffolk County, Massachusetts, United States
from $298
VRBO
4.7
View deal
Fishing
House ∙ 10 guests ∙ 4 bedrooms
Harbor View / Orient Heights, Boston, Massachusetts, United States
from $429
VRBO
4.9
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Popular Rental Amenities in Winthrop

  • Internet (193)
  • Kitchen (187)
  • TV (181)
  • No smoking (173)
  • Microwave (161)
  • AC (151)
  • Washer (124)
  • Dishwasher (113)
  • Pet allowed (99)
  • Parking (87)
  • Balcony/Patio (78)
  • No pets (72)
Listed above are the most popular filters in Winthrop and the number of rentals that include them. In Winthrop, 139 accommodations provide "TVs". So, if you want to tune out with some TV time, select the TVs filter to compare these rentals. Not as many properties in Winthrop are available if you want to hang out and relax outside or if you like to end your days curled up by the fire as "fireplaces" and "yards" are not often available in this destination.

Price and Availability Index in Winthrop

Vacation Rental Price Information in Winthrop

The price graph will give you the nightly price average for the upcoming months of the year. Winthrop is more expensive in July (7/6 - 7/13), where prices are on average $282 a night. Prices drop in January to an average of $221 per night (1/12 - 1/19).

Rental Availability Information in Winthrop

The graph shows the weekly availability rate in Winthropfor the next twelve months. The most challenging week to find a rental in the next twelve months is in September (9/7 - 9/14). The week with the highest percentage of available rentals is in January (1/5 - 1/12).

The Weather in Winthrop

37°
25°
39°
23°
46°
30°
57°
41°
66°
52°
75°
59°
82°
66°
81°
66°
73°
59°
63°
48°
52°
37°
45°
32°
Jan.
Feb.
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May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. In the next 6 months, July will have higher average temperatures. Conversely, February is the coolest month in Winthrop, with temperatures going under 23° The rainiest month is July while the driest month is August.

Accommodations in Winthrop

More than half of the offers (51.45%) in Winthrop are apartment rentals. They are the most common properties in this destination. Additionally, the average size of apartment rentals in Winthrop is 1,030 ft² with an average price of $322 a night. Furthermore, this category of residence is an excellent option for medium-sized groups and families, as the majority of apartment rentals can host 4 people. Users who prefer something other than apartment rentals will also find many hotel rooms, which are the other most popular property type in Winthrop. Our data shows that the average price of hotel rooms is $301 a night for an area of 360 ft².

Fish, go boating, or swim off the coast near Winthrop vacation rentals

Your vacation rental in Winthrop, Massachusetts, is positioned strategically near to the big city, whilst offering you the small town serenity of coastal living. Take a boat out on the water, or explore the Belle Isle Marsh Reservation.

Show all 243 properties
Family Activities

History and natural heritage

There's so much to do on the Boston Harbor Islands. Visit historic Fort Warren with its intriguing exhibits. Bring the kids to the islands and search the shore for clams and mussels. You can also come boating and fishing on the sparkling water that licks the islands. In the summer, you can enjoy live performances by the stunning coast, together with your family.

Local Attractions

Coastal excursions

Explore the coastline at Boston Harbor Islands National Recreation Area. You'll spot a huge variety of wildlife on your trip, from deer to fox and glittering dragonflies. Relax at the beach and enjoy one of New England's most attractive vistas of shoreline, or venture to the summit of the lighthouse and look out on the waves.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Winthrop VRBO Vacation Rentals in Winthrop HomeAway Vacation Rentals in Winthrop TripAdvisor Vacation Rentals in Winthrop VacationRentals.com Vacation Rentals in Winthrop HouseTrip Vacation Rentals in Winthrop FlipKey Vacation Rentals in Winthrop 9flats.com Vacation Rentals in Winthrop VaycayHero Vacation Rentals in Winthrop PerfectPlaces.com Vacation Rentals in Winthrop Homestay.com Vacation Rentals in Winthrop Only-apartments Vacation Rentals in Winthrop Interhome Vacation Rentals in Winthrop Bedycasa Vacation Rentals in Winthrop Novasol Vacation Rentals in Winthrop HomeEscape Vacation Rentals in Winthrop

Vacation Destinations Near Winthrop