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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Winthrop holiday rentals

A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

1. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (657 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is S$470
includes taxes & fees
7 Sept - 8 Sept
Marriott Vacation Club® at Custom House, Boston
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

2. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (447 reviews)
"Great location so close to everything"
United States
Hunter
The price is S$222
includes taxes & fees
24 Aug - 25 Aug
Temple Place Suites
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

3. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (142 reviews)
"Worth the stay"
Canada
Akansha
The price is S$322
includes taxes & fees
24 Aug - 25 Aug
Maverick Suites at 40 Temple St
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

4. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (330 reviews)
"Lovely apartment and great stay. Location is very good with lots to do around"
United States
Obianuju
The price is S$209
includes taxes & fees
25 Aug - 26 Aug
Premier Suites - Bay Village
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

5. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (16 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is S$400
includes taxes & fees
8 Sept - 9 Sept
The Concord Hotel
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

6. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (736 reviews)
"Great for the price; central to everything"
United States
afshin
The price is S$413
includes taxes & fees
27 Aug - 28 Aug
Global Luxury Suites Downtown Boston
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

7. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (37 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is S$417
includes taxes & fees
8 Sept - 9 Sept
The Chester Hotel
A row of brick buildings with storefronts, including a bakery and a liquor store.

8. 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, (200 reviews)
"Great location, really cool place!"
United States
lane
The price is S$326
includes taxes & fees
31 Aug - 1 Sept
Maverick Suites at 245 Newbury St
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.

9. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (166 reviews)
"Well located"
United States
Evelyn
The price is S$332
includes taxes & fees
24 Aug - 25 Aug
Maverick Suites at 400 Columbus Ave
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

10. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (408 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
The price is S$344
includes taxes & fees
25 Aug - 26 Aug
Maverick Suites at 28 Fenway
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 Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Lovely hotel in an excellent location one block from Boston Commons."
Susan 4-night trip
Posted 1 hour ago
The Godfrey Hotel Boston

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.

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 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.