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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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
9.4 out of 10, Exceptional, (678 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 RM1,115
RM1,281 total
includes taxes & fees
25 Nov - 26 Nov
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, (769 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is RM453
RM1,004 total
includes taxes & fees
22 Nov - 23 Nov
Global Luxury Suites Downtown Boston
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

3. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (41 reviews)
"Location was very loud but thank God for earplugs. It was very clean but very old. Very expensive for such a location and room. I always believe in paying for what u get but I paid a lot for 3 nights."
United States
Luda
The price is RM471
RM1,058 total
includes taxes & fees
1 Nov - 2 Nov
The Chester Hotel
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

4. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,333 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is RM621
RM694 total
includes taxes & fees
31 Oct - 1 Nov
Crescent Suites Hotel
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

5. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (338 reviews)
"Clean hotel. The space was very nice and open, Very accessible to everything I needed"
United States
Krista
The price is RM735
RM1,213 total
includes taxes & fees
9 Nov - 10 Nov
Kasa Boston at Fenway
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.

6. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (43 reviews)
"We loved the location and the host was amazing. We only wish the sidewalk construction wasn’t going on because it obstructed part of the beautiful view."
United States
Jodi
The price is RM3,772
RM5,040 total
includes taxes & fees
26 Oct - 27 Oct
The Monty Boston
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

7. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (460 reviews)
"Great price for the place given the location."
United States
Beenish
The price is RM467
RM936 total
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 28 Fenway
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

8. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (36 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is RM655
RM1,269 total
includes taxes & fees
22 Nov - 23 Nov
The Concord Hotel
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

9. 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, (159 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 RM513
RM965 total
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 40 Temple St
A row of brick buildings with storefronts, including a bakery and a liquor store.

10. 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, (210 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is RM529
RM984 total
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 245 Newbury St
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

Omni Parker House

Omni Parker House

8/10 Good
"Maintenance and cleaning love should be done"
Sylvain 2-night trip
Posted less than an hour ago
Omni Parker House

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, 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.

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.