Winthrop Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Winthrop holiday rentals

Interior

Apartment in Winthrop

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches
9.6 out of 10, Exceptional, (7 reviews)
"Great location and wonderful hosts! Would definitely recommend to anyone staying in the Boston area. "
United States
Kristie P.
The price is HK$897
HK$1,873 total
includes taxes & fees
29 Jan - 30 Jan
Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches
Exterior

Houseboat in Charlestown

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
9.8 out of 10, Exceptional, (200 reviews)
"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 HK$585
HK$3,434 total
includes taxes & fees
29 Jan - 30 Jan
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Property grounds

Houseboat in Thompson Square - Bunker Hill

Charlestown Houseboat Walk to attractions Be rocked to sleep
9.6 out of 10, Exceptional, (99 reviews)
"Great location, pet friendly, "
United States
Karen W.
The price is HK$507
HK$3,030 total
includes taxes & fees
4 Feb - 5 Feb
Charlestown Houseboat Walk to attractions Be rocked to sleep
Interior

Houseboat in Boston

Fun houseboat. Walk to Boston attractions WIFI
9.8 out of 10, Exceptional, (89 reviews)
"It was unique way to stay in the city"
United States
brian m.
The price is HK$663
HK$2,968 total
includes taxes & fees
29 Jan - 30 Jan
Fun houseboat. Walk to Boston attractions WIFI
Lobby lounge

Aparthotel in Chinatown

Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (655 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
Global Luxury Suites Downtown Boston
Exterior

Aparthotel in Back Bay

Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (157 reviews)
"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
Interior

Apartment in South End

Furnished Apartment near BMC
3.0 star property
The price is HK$667
HK$1,843 total
includes taxes & fees
29 Jan - 30 Jan
Furnished Apartment near BMC
Front of property

Aparthotel in Beacon Hill

Maverick Suites at 40 Temple St
2.0 star property
7.6 out of 10, Good, (103 reviews)
"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
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Downtown Boston

Boston Financial District 1BR | Walk to anything!
The price is HK$734
HK$2,038 total
includes taxes & fees
2 Feb - 3 Feb
Boston Financial District 1BR | Walk to anything!
42-inch TV with satellite channels

Aparthotel in South End

Maverick Suites at 400 Columbus Ave
2.0 star property
7.2 out of 10, Good, (135 reviews)
"everything was great! only thing i’ll say is that the dots have some cracks where people can see in on the bathrooms and some rooms, but other than that i’d start here again!"
United States
Maelynn
Maverick Suites at 400 Columbus Ave
Desk, iron/ironing board, free WiFi, bed sheets

Apartment in Downtown Boston

Temple Place Suites
2.5 star property
7.0 out of 10, Good, (331 reviews)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is HK$702
HK$1,300 total
includes taxes & fees
29 Jan - 30 Jan
Temple Place Suites
Living area

Aparthotel in South End

The Chester Hotel
4.0 star property
8.6 out of 10, Excellent, (28 reviews)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is HK$1,235
HK$2,809 total
includes taxes & fees
29 Jan - 30 Jan
The Chester Hotel
Exterior

Apartment in Downtown Boston

Best Location Studio In Downtown Boston
10.0 out of 10, Exceptional, (1 review)
"In town to celebrate a special event."
United States
Pam P.
The price is HK$881
HK$1,768 total
includes taxes & fees
2 Feb - 3 Feb
Best Location Studio In Downtown Boston
Desk, laptop workspace, free WiFi, bed sheets

Aparthotel in Bay Village

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

Condo in Beacon Hill

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
10.0 out of 10, Exceptional, (2 reviews)
"Had a wonderful stay! Beautiful condo in a beautiful neighborhood that is walking distance to the commons."
United States
Grant T.
The price is HK$755
HK$2,096 total
includes taxes & fees
2 Feb - 3 Feb
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Iron/ironing board, free WiFi, bed sheets

Aparthotel in Bay Village

Premier Suites - Bay Village
2.0 star property
6.2 out of 10, (257 reviews)
"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
Premier Suites - Bay Village
Fridge, microwave, oven, stovetop

Holiday Home in North End

3BR3Bth Entire House/Steps to Downtown & TD Garden
10.0 out of 10, Exceptional, (5 reviews)
"Clean and bright throughout, host was great with timely responses to all inquiries. Maybe not the best for young children bc of the all the stairs (which are beautiful btw)."
United States
Margaret S.
The price is HK$1,710
HK$4,244 total
includes taxes & fees
29 Jan - 30 Jan
3BR3Bth Entire House/Steps to Downtown & TD Garden
1 bedroom, desk, iron/ironing board, WiFi

Apartment in Bay Village

Studio Awaits Your Next Stay!
9.2 out of 10, Wonderful, (5 reviews)
"Would stay again"
United States
mark p.
The price is HK$881
HK$1,768 total
includes taxes & fees
4 Feb - 5 Feb
Studio Awaits Your Next Stay!
1 bedroom, desk, iron/ironing board, WiFi

Apartment in Downtown Boston

Perfect One Bedroom Stay In Downtown Boston!
8.6 out of 10, Excellent, (18 reviews)
"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 HK$905
HK$1,795 total
includes taxes & fees
4 Feb - 5 Feb
Perfect One Bedroom Stay In Downtown Boston!
Marina

Condo in Marblehead Historic District

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
10.0 out of 10, Exceptional, (71 reviews)
"The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again."
United States
Pamela O.
The price is HK$582
HK$1,809 total
includes taxes & fees
29 Jan - 30 Jan
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
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

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Amazing gym! Clean rooms and great amenities. Beds were comfortable. We were snowed in and the hotel restaurants stayed open when everything in Boston was shut down."
Hazel 1-night trip
Posted 1 day ago
Seaport Hotel 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!

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Frequently asked questions

Can I find a holiday rental in Winthrop?

Yes, we give you a choice of holiday rentals where you'll be only 3.7 mi (6 km) from New England Aquarium, providing 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 cafés and waterfront during your trip.

What are some of the best holiday rentals that Winthrop has to offer?

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino: This holiday home rental outside of Winthrop is located on the waterfront, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Winthrop?

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

What can I see and do in Winthrop?

Boston Harbor Islands State Park and Donovan 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 holiday rentals like in Winthrop?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winthrop. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip.