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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winthrop holiday rentals

A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

1. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (152 reviews)
"There only a few things I require from a hotel. Hotel Maverick Suites at 40 are clean, quiet and reasonably priced. I enjoyed my stay there immensely. A bonus was their convenient location."
United States
Jerrold
The price is 3.017.091 ₫
5.857.910 ₫ 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.

2. 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, (206 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is 5.841.228 ₫
9.104.255 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 245 Newbury St
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
7.4 out of 10, Good, (26 reviews)
"Cute space! Wasn’t too difficult navigating Boston from this location."
United States
Rebecca
The price is 6.314.841 ₫
10.544.836 ₫ total
includes taxes & fees
27 Oct - 28 Oct
The Concord Hotel
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

4. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (434 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is 3.484.857 ₫
6.544.969 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 28 Fenway
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

5. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (490 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is 2.502.548 ₫
4.519.642 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Temple Place Suites
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

6. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (323 reviews)
"Excellent property upscale amenities full kitchen perfect in every way and my room was only a studio I’ll definitely be back next time to try a larger room just to see what they’re like"
United States
Dirk
The price is 6.431.782 ₫
10.081.819 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Kasa Boston at Fenway
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, (39 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 5.561.218 ₫
9.678.546 ₫ total
includes taxes & fees
5 Oct - 6 Oct
The Chester Hotel
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

8. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,297 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is 3.952.623 ₫
4.415.080 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Crescent Suites Hotel
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

9. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (758 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is 4.630.883 ₫
8.449.332 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Global Luxury Suites Downtown Boston
A wooden hallway with a patterned floor leading to a door.

10. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (326 reviews)
"Room was clean, neat area."
United States
Keir
The price is 3.595.952 ₫
6.338.877 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Maverick Suites at 89 Marion
A modern hotel room with a bed, a desk, a sofa, and a dining area.

11. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (239 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is 5.925.036 ₫
11.291.871 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Charlesgate Suites
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

citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"Staff-amazing! Love the vibe. Best location for transportation and great value for all!"
Michelle 3-night trip
Posted 2 hours ago
citizenM Boston North Station

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.