Winthrop Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jan 8 - Jan 9
Tomorrow
Jan 9 - Jan 10
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Winthrop vacation rentals

Interior
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
Winthrop
10.0 out of 10, Exceptional, (52)
"Owner was easy to communicate with. "
Canada
Ronald
The price is ￥31,732
￥59,600 total
includes taxes & fees
Feb 6 - Feb 7
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
Exterior
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (200)
"My husband and I had an excellent stay! It was very comfortable! I would highly recommend staying on The Blue Pearl and hope to stay there again. "
United States
Stacey W.
The price is ￥10,969
￥67,909 total
includes taxes & fees
Jan 9 - Jan 10
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Outdoor dining
Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by

Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by

Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
Thompson Square - Bunker Hill
10.0 out of 10, Exceptional, (57)
"Amazing location, Boston is a favorite of ours. Go Sox"
United States
jeff w.
The price is ￥38,783
￥70,703 total
includes taxes & fees
Jan 9 - Jan 10
Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
Property grounds
Charlestown Houseboat Walk to attractions Be rocked to sleep

Charlestown Houseboat Walk to attractions Be rocked to sleep

Charlestown Houseboat Walk to attractions Be rocked to sleep
Thompson Square - Bunker Hill
9.6 out of 10, Exceptional, (99)
"Great location, pet friendly, "
United States
Karen W.
The price is ￥12,536
￥63,766 total
includes taxes & fees
Jan 9 - Jan 10
Charlestown Houseboat Walk to attractions Be rocked to sleep
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
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
7.2 out of 10, Good, (134)
"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
The price is ￥13,625
￥30,073 total
includes taxes & fees
Feb 1 - Feb 2
Maverick Suites at 400 Columbus Ave
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | 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, (329)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is ￥11,141
￥22,713 total
includes taxes & fees
Jan 22 - Jan 23
Temple Place Suites
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, (639)
"Very clean, beautiful place. I would stay there again."
Canada
Liam
The price is ￥13,100
￥22,082 total
includes taxes & fees
Jan 13 - Jan 14
Global Luxury Suites Downtown Boston
Iron/ironing board, WiFi, bed sheets
The Chester: Hip, Renovated, South End

The Chester: Hip, Renovated, South End

The Chester: Hip, Renovated, South End
2.0 star property
South End
10.0 out of 10, Exceptional, (2)
"Nice room. Good location "
United States
Abenamar A.
The price is ￥18,334
￥45,482 total
includes taxes & fees
Jan 9 - Jan 10
The Chester: Hip, Renovated, South End
Premium Apartment | Living area | 24-inch Smart TV with digital channels
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 ￥17,051
￥47,519 total
includes taxes & fees
Jan 12 - Jan 13
The Chester Hotel
Deluxe Double Room, Shared Bathroom | 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
6.2 out of 10, (256)
"We stayed there for four days. The heaters were not working, I got almost sick. And the customer service was awful. I hope you will find better place to stay"
United States
Aziza
The price is ￥12,411
￥22,371 total
includes taxes & fees
Jan 16 - Jan 17
Premier Suites - Bay Village
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, (103)
"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
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
1 bedroom, desk, iron/ironing board, WiFi
Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
9.2 out of 10, Wonderful, (5)
"Would stay again"
United States
mark p.
The price is ￥12,693
￥29,248 total
includes taxes & fees
Jan 22 - Jan 23
Studio Awaits Your Next Stay!
1 bedroom, desk, iron/ironing board, WiFi
Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.6 out of 10, Excellent, (18)
"Temple Place Suites was a great place to stay for our few days in Boston. We loved being across from Boston Commons, near great bakerys and cafes. It was a comfortable apartment with great space and plenty of amenities. Staff was great at communicating about check in, building codes and check out. Wished there were dish towels and wash cloths. Otherwise, it was great!!"
United States
Christine
The price is ￥16,140
￥33,496 total
includes taxes & fees
Jan 9 - Jan 10
Perfect One Bedroom Stay In Downtown Boston!
Exterior
North End Gem ★ Prime Location + Parking Included

North End Gem ★ Prime Location + Parking Included

North End Gem ★ Prime Location + Parking Included
North End
9.6 out of 10, Exceptional, (59)
"Had a very nice time close to everything walking distance to alot of fun and exciting things "
United States
Lynn W.
The price is ￥20,058
￥54,538 total
includes taxes & fees
Jan 9 - Jan 10
North End Gem ★ Prime Location + Parking Included
Exterior
Best Location Studio In Downtown Boston

Best Location Studio In Downtown Boston

Best Location Studio In Downtown Boston
Downtown Boston
10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
The price is ￥11,126
￥27,399 total
includes taxes & fees
Jan 22 - Jan 23
Best Location Studio In Downtown Boston
TV, offices
Come Visit Boston and Stay In Our Homey Studio

Come Visit Boston and Stay In Our Homey Studio

Come Visit Boston and Stay In Our Homey Studio
Downtown Boston
8.8 out of 10, Excellent, (3)
"Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!"
United States
Dean and Courtenay M.
The price is ￥11,126
￥27,399 total
includes taxes & fees
Jan 22 - Jan 23
Come Visit Boston and Stay In Our Homey Studio
Apartment | 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
8.6 out of 10, Excellent, (9)
"Great place. Very clean. Great communication."
United States
Michele
The price is ￥18,926
￥38,644 total
includes taxes & fees
Jan 9 - Jan 10
Furnished Apartments near Encore Boston
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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"everything was great!"
Agnes 3-night trip
Posted 5 hours ago
Harborside Inn Of Boston

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.

What are some of the best vacation home rentals in Winthrop?

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi: This vacation home rental near Winthrop is located in the city center and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 TD Garden and Fenway Park.

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.