A coastal town with a lighthouse, sandy beach, and residential buildings.

Winthrop Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winthrop holiday rentals

A paved pathway leading to a waterfront, with trees and a building on one side.

1. Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Winthrop
9.2 out of 10, Wonderful, (22 reviews)
"Very amazing room to stay! Everything was very clean and comfortable! Host was very responsive and wonderful!"
United States
Edmund W.
The price is HK$824
HK$1,718 total
includes taxes & fees
10 Nov - 11 Nov
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
A dining area with a round table set for four, a sofa in the background, and a decorative wall piece.

2. Steps from the ocean - minutes from Boston

Steps from the ocean - minutes from Boston
Winthrop
9.8 out of 10, Exceptional, (6 reviews)
The price is HK$1,460
HK$2,963 total
includes taxes & fees
19 Nov - 20 Nov
Steps from the ocean - minutes from Boston
A modern kitchen with wooden cabinets, a refrigerator, and a dining area with chairs.

3. Beautiful 3-bedroom apartment with AC in welcoming Winthrop

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
The price is HK$2,354
HK$3,234 total
includes taxes & fees
5 Nov - 6 Nov
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

4. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (51 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
The price is HK$753
HK$2,264 total
includes taxes & fees
9 Nov - 10 Nov
Bright 2BR by Boston Waterfront
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

5. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (772 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is HK$846
HK$1,900 total
includes taxes & fees
29 Nov - 30 Nov
Global Luxury Suites Downtown Boston
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

6. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (38 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is HK$1,257
HK$2,437 total
includes taxes & fees
9 Nov - 10 Nov
The Concord Hotel
A modern living room with a sofa, coffee table, and a small table with books and a lamp. There is a kitchen area with cabinets, a refrigerator, and a microwave. A welcome sign is on the wall, and a basketball arcade game is visible.

7. Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
8.6 out of 10, Excellent, (10 reviews)
"It was close to Boston and the airport"
United States
Lewis
The price is HK$1,193
HK$2,814 total
includes taxes & fees
5 Nov - 6 Nov
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

8. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (164 reviews)
"Great property in a great location. Tons of food options nearby. Walking distance to Target and Whole Foods. Easy access to the Blue line. The neighborhood was quiet and clean. Boston common is just a block away. Definitely would stay again and highly recommend."
United States
TommyWallace
The price is HK$791
HK$1,631 total
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 40 Temple St
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

9. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (347 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is HK$1,412
HK$2,330 total
includes taxes & fees
10 Nov - 11 Nov
Kasa Boston at Fenway
A room with a large window overlooking a marina with boats and buildings.

10. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (120 reviews)
"The houseboat was great! Everyone was super friendly and helpful. Can’t wait for our next stay!"
United States
Frank M.
The price is HK$969
HK$3,685 total
includes taxes & fees
30 Nov - 1 Dec
Fun houseboat. Walk to Boston attractions WIFI
A row of brick buildings with storefronts, including a bakery and a liquor store.

11. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (216 reviews)
"Great location - plenty to do."
United States
Chloe
The price is HK$1,130
HK$2,020 total
includes taxes & fees
22 Nov - 23 Nov
Maverick Suites at 245 Newbury St
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

12. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (680 reviews)
"I can’t believe this property is a hotel and not a historic landmark. If you like historical places this is the place to stay in Boston."
United States
Benny
The price is HK$1,794
HK$2,062 total
includes taxes & fees
25 Nov - 26 Nov
Marriott Vacation Club® at Custom House, Boston
A kitchen with a bar area, wooden paneling, and a view of a dock.

13. 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, (213 reviews)
"Wonderful brief stay!"
United States
Marie T.
The price is HK$1,155
HK$4,214 total
includes taxes & fees
8 Nov - 9 Nov
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

14. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (42 reviews)
"Charming historic building with modern room interiors and amenities, high quality linens/towels, and an easy walk to BSO, Northeastern University, and shopping."
United States
Andrew
The price is HK$1,130
HK$2,291 total
includes taxes & fees
10 Nov - 11 Nov
The Chester Hotel
A living room with a sofa, two chairs, a coffee table, and a TV.

15. Boston Financial District 1BR | Walk to anything!

Boston Financial District 1BR | Walk to anything!
Downtown Boston
9.6 out of 10, Exceptional, (4 reviews)
"The place was as advertised: clean, within walking distance to a lot of places. Note that Its central location, while convenient, is also a drawback due to road noise. Make sure you pack a very good set of ear plugs, not the foam cheapo ones that airlines give you for free. You will need them to block out the traffic noise from below your bedroom window."
United States
Popsicle T.
The price is HK$887
HK$2,190 total
includes taxes & fees
30 Nov - 1 Dec
Boston Financial District 1BR | Walk to anything!
A historic building with a prominent tower and a cherry blossom tree in front.

16. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
9.0 out of 10, Wonderful, (24 reviews)
"Great location."
United States
Chloe
The price is HK$581
HK$1,645 total
includes taxes & fees
23 Nov - 24 Nov
Stunning Back Bay Studio Apartment
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

17. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (473 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is HK$805
HK$1,692 total
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 28 Fenway
A historic building with a prominent tower and a cherry blossom tree in front.

18. Modern Studio | South End

Modern Studio | South End
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"Amazing stay in the best location! Would recommend and stay here again!!"
United States
Kaylee P.
The price is HK$567
HK$1,526 total
includes taxes & fees
23 Nov - 24 Nov
Modern Studio | South End
A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

19. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (186 reviews)
"Very well located. Close to two subways and Copeland Square."
Canada
Lorne
The price is HK$890
HK$1,744 total
includes taxes & fees
2 Dec - 3 Dec
Maverick Suites at 400 Columbus Ave
A historic building with a prominent tower and a cherry blossom tree in front.

20. Stellar South End Studio

Stellar South End Studio
Back Bay
9.4 out of 10, Exceptional, (6 reviews)
"The room was clean and quiet."
United States
Beth
The price is HK$667
HK$1,755 total
includes taxes & fees
22 Nov - 23 Nov
Stellar South End Studio
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

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 holiday rental in Winthrop?

Yes, there are holiday rentals close to the most popular sights in Winthrop, or you can select a more secluded option if you're looking for a relaxing stay. 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?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This holiday home rental outside of Winthrop offers a patio, a garden and air conditioning 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

How many holiday rentals are there in Winthrop?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

Winthrop Beach 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 Fenway Park and Faneuil Hall Marketplace.

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.