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Winthrop Vacation Rentals

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Winthrop vacation rentals

Lobby lounge
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (637)
"Very clean, beautiful place. I would stay there again."
Canada
Liam
Global Luxury Suites Downtown Boston
Front of property
Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (102)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
Maverick Suites at 40 Temple St
Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (201)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is P8,927
P20,389 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charlesgate Suites
Exterior
Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very Good, (155)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St
Living area
The Monty Boston

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (29)
"Amazing property, would stay again."
United States
Doug
The price is P29,995
P44,606 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Monty Boston
Private kitchen
Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (68)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 Columbus Ave
Individually furnished, iron/ironing board, free WiFi, bed sheets
Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (327)
"Good place"
United States
Elijah
The price is P5,030
P11,530 total
includes taxes & fees
Dec 28 - Dec 29
Maverick Suites at 28 Fenway
Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is P8,789
P20,584 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Chester Hotel
Interior entrance
Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner South Side
8.2 out of 10, Very Good, (270)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
Maverick Suites at 89 Marion
Rooftop terrace
Global Luxury Suites East Boston

Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
7.0 out of 10, Good, (177)
"The place was very nice and nicely equipped, but a little difficult to locate."
United States
William
The price is P8,048
P11,888 total
includes taxes & fees
Dec 29 - Dec 30
Global Luxury Suites East Boston
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (133)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
Maverick Suites at 400 Columbus Ave
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (252)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Exterior
Broom & Board

Broom & Board

Broom & Board
3.5 star property
Salem
10.0 out of 10, Exceptional, (1)
"Great stay highly recommended!"
United States
Jamie
Broom & Board
Private kitchen
Apartments in Salem

Apartments in Salem

Apartments in Salem
3.0 star property
Salem
8.0 out of 10, Very Good, (48)
"Property was fine. It is well located to see the sites in Salem. Only negative was that the neighbors were a bit loud at night. "
United States
Wes
Apartments in Salem
Interior
1 Mi to Downtown: Salem Vacation Rental!

1 Mi to Downtown: Salem Vacation Rental!

1 Mi to Downtown: Salem Vacation Rental!
3.0 star property
Salem
10.0 out of 10, Exceptional, (2)
"Great overall stay! "
United States
Tessa
The price is P6,813
P19,367 total
includes taxes & fees
Dec 28 - Dec 29
1 Mi to Downtown: Salem Vacation Rental!
Property grounds
Crescent Suites Hotel

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1145)
"Lovely, quiet place."
United States
Fatu
Crescent Suites Hotel
2 bedrooms, desk
Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is P17,043
P44,645 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Coastal Charm Lobster Ch Teau
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (252)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is P5,991
P9,924 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Premier Suites - Bay Village
1 bedroom, desk, laptop workspace, free WiFi
Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.4 out of 10, Very Good, (8)
"Great place. Very clean. Great communication."
United States
Michele
The price is P8,942
P16,559 total
includes taxes & fees
Dec 27 - Dec 28
Furnished Apartments near Encore Boston
Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (327)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is P5,286
P9,789 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Temple Place Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winthrop Hotel Reviews

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

10/10 Excellent
"Very conveniently located. Best location if taking Amtrak"
Dunnapar F 2-night trip
Posted 2 days ago
The Westin Copley Place, Boston, a Marriott Hotel

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop using one of the methods below:

  • View our selection of featured holiday rentals in Winthrop
  • Use the map to find apartments and other holiday homes in the Winthrop neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winthrop while they last

Look no further and take a look at our great range of rental properties in Winthrop!

Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals where you'll be only 3.7 mi (6 km) from New England Aquarium, giving you a more secluded option to escape the hustle and bustle. Visitors to Winthrop speak positively about the beaches and restaurants in this destination. Make sure you have time to check out the cafes and waterfront during your trip.

How many vacation rentals are there in Winthrop?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

Boston Harbor Islands State Park and Winthrop Beach are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include Fenway Park and New England Aquarium.

What are vacation rentals like in Winthrop?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Winthrop. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.