Winthrop Vacation Rentals

Compare 226 available properties from 16 providers
Winthrop
Save up to 32%

Best vacation home deals in Winthrop

$329
from $268
-19%
1190 ft² House
6 3
Revere, Suffolk County, Massachusetts, United States
Found on
VRBO
$717
from $485
-32%
890 ft² Apartment
4 2
Waterfront, Boston, Massachusetts, United States
Found on
VRBO
$345
from $261
-24%
House
5 2
North End, Boston, Massachusetts, United States
Found on
VRBO

Compare and find the perfect property for as little as $54 per night by searching among the 226 properties available in Winthrop. HomeToGo, a vacation rental search engine, directly sorts all of these vacation rentals so you can save up to 32%!

Recommended vacation rentals in Winthrop

Rent a vacation accommodation in Winthrop: from $54 per night

from $170
800 ft² Apartment
3 1
East Boston, Boston, Massachusetts, United States
4.6
"Excellent" 21 reviews
Found on VRBO
from $226
1190 ft² Apartment
6 2
Harbor View / Orient Heights, Boston, Massachusetts, United States
4.8
"Excellent" 11 reviews
Found on VRBO
from $185
Apartment
2 1
Jeffries Point, Boston, Massachusetts, United States
4.9
"Excellent" 13 reviews
Found on VRBO
from $143
Apartment
4 2
Chelsea, Suffolk County, Massachusetts, United States
4.9
"Excellent" 62 reviews
Found on VRBO
$270
from $209
-23%
House
6 2
Revere, Suffolk County, Massachusetts, United States
4.3
"Outstanding" 13 reviews
Found on VRBO
from $301
Apartment
6 3
Jeffries Point, Boston, Massachusetts, United States
4.3
"Outstanding" 4 reviews
Found on VRBO
$497
from $301
-39%
810 ft² Apartment
4 1
Seaport District, Boston, Massachusetts, United States
5.0
"Excellent" 1 review
Found on VRBO
$429
from $230
-46%
House
8 3
Revere, Suffolk County, Massachusetts, United States
5.0
"Excellent" 3 reviews
Found on VRBO
See all offers

  Apartments with a balcony or patio

from $279
980 ft² Apartment
5 2
Central-Maverick Square / Paris Street, Boston, Massachusetts, United States
4.7
"Excellent" 49 reviews
Found on VRBO
from $169
5020 ft² Apartment
4 2
Revere, Suffolk County, Massachusetts, United States
4.5
"Excellent" 2 reviews
Found on Wimdu
$325
from $219
-33%
800 ft² Apartment
6 2
Central-Maverick Square / Paris Street, Boston, Massachusetts, United States
4.8
"Excellent" 50 reviews
Found on VRBO
$260
from $197
-24%
950 ft² Apartment
4 2
Revere, Suffolk County, Massachusetts, United States
5.0
"Excellent" 17 reviews
Found on VRBO
See all offers

  Vacation homes with fishing spots nearby

from $429
3000 ft² House
10 4
Harbor View / Orient Heights, Boston, Massachusetts, United States
4.9
"Excellent" 77 reviews
Found on VRBO
from $327
Apartment
10 3
Harbor View / Orient Heights, Boston, Massachusetts, United States
5.0
"Excellent" 1 review
Found on VRBO
from $170
Apartment
3
North End, Boston, Massachusetts, United States
4.9
"Excellent" 179 reviews
Found on VRBO
from $440
1190 ft² Boat
6 3
Boston, Suffolk County, Massachusetts, United States
4.7
"Excellent" 6 reviews
Found on VRBO
See all offers

  Best dog-friendly rentals

$402
from $272
-32%
1000 ft² Apartment
6 3
Central-Maverick Square / Paris Street, Boston, Massachusetts, United States
4.4
"Outstanding" 50 reviews
Found on VRBO
from $290
1190 ft² Apartment
7 3
Central-Maverick Square / Paris Street, Boston, Massachusetts, United States
5.0
"Excellent" 5 reviews
Found on VRBO
$292
from $178
-39%
1190 ft² Apartment
8 5
Central-Maverick Square / Paris Street, Boston, Massachusetts, United States
5.0
"Excellent" 2 reviews
Found on VRBO
from $192
Apartment
2 1
North End, Boston, Massachusetts, United States
4.3
"Outstanding" 4 reviews
Found on VRBO
See all offers

Popular rental amenities in Winthrop

  • Kitchen (142)
  • TV (138)
  • No smoking (136)
  • Internet (135)
  • AC (124)
  • Microwave (113)
  • Dishwasher (76)
  • Parking (76)
  • Washer (73)
  • No pets (61)
  • Balcony/Patio (52)
  • Pets OK (47)
Listed above are the most popular filters in Winthrop and the number of rentals that include them. In Winthrop, 952 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 enjoy soaking in the hot tub or if you want to sweat it out in a sauna as "saunas" and "Jacuzzis" are not often available in this destination.

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.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. On average, the warmest month is July. However, temperatures can go lower than 23° in Winthrop in February. According to the climate diagram, December is the rainiest month of the year in Winthrop.

More than half of the offers (58.22%) in Winthrop are apartment rentals. They are the most common properties in this destination. Additionally, the average size of apartment rentals in Winthrop is 1,430 ft² with an average price of $326 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 5 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 $310 a night for an area of 350 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 226 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 250 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 Wimdu 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