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

Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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, (665 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is RM1,909
RM2,194 total
includes taxes & fees
13 Sept - 14 Sept
Marriott Vacation Club® at Custom House, Boston
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

2. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (741 reviews)
"Great for the price; central to everything"
United States
afshin
The price is RM1,106
RM1,772 total
includes taxes & fees
11 Sept - 12 Sept
Global Luxury Suites Downtown Boston
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

3. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (21 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 RM857
RM1,500 total
includes taxes & fees
11 Sept - 12 Sept
The Concord Hotel
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

4. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (145 reviews)
"Worth the stay"
Canada
Akansha
The price is RM552
RM1,009 total
includes taxes & fees
13 Sept - 14 Sept
Maverick Suites at 40 Temple St
A row of brick buildings with storefronts, including a bakery and a liquor store.

5. 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, (202 reviews)
"Great location, really cool place!"
United States
lane
The price is RM877
RM1,382 total
includes taxes & fees
21 Sept - 22 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.

6. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (171 reviews)
"Well located"
United States
Evelyn
The price is RM658
RM1,130 total
includes taxes & fees
21 Sept - 22 Sept
Maverick Suites at 400 Columbus Ave
A modern kitchen with a central island, a dining area with a round table and chairs, and a large window providing a view of the city at night.

7. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (40 reviews)
"This place is absolutely stunning I would definitely book again. "
United States
Klaudia
The price is RM2,041
RM3,048 total
includes taxes & fees
29 Sept - 30 Sept
The Monty Boston
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

8. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (314 reviews)
"Everything is good"
United States
Kilyen
The price is RM641
RM1,158 total
includes taxes & fees
13 Sept - 14 Sept
Kasa Boston at Fenway
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

9. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is RM696
RM1,314 total
includes taxes & fees
11 Sept - 12 Sept
The Chester Hotel
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

10. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (466 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is RM491
RM821 total
includes taxes & fees
13 Sept - 14 Sept
Temple Place Suites
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

11. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (419 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is RM810
RM1,329 total
includes taxes & fees
13 Sept - 14 Sept
Maverick Suites at 28 Fenway
A modern hotel room with a bed, a desk, a sofa, and a dining area.

12. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (233 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is RM834
RM1,661 total
includes taxes & fees
13 Sept - 14 Sept
Charlesgate Suites
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

13. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (339 reviews)
"Location is great"
United States
Eria
The price is RM491
RM775 total
includes taxes & fees
13 Sept - 14 Sept
Premier Suites - Bay Village
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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"No"
Meaghan 1-night trip
Posted 1 hour ago
Hyatt Regency Boston/Cambridge

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia.co.uk! 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, 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 Massachusetts Bay 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 Boston Harbor.

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.