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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 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
9.4 out of 10, Exceptional, (673 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$773
includes taxes & fees
2 Nov - 3 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, (759 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is S$476
includes taxes & fees
2 Nov - 3 Nov
Global Luxury Suites Downtown Boston
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

3. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (324 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 S$496
includes taxes & fees
1 Nov - 2 Nov
Kasa Boston at Fenway
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, (1,306 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is S$182
includes taxes & fees
1 Nov - 2 Nov
Crescent Suites Hotel
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

5. 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, (153 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 S$288
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 40 Temple St
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

6. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (40 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 S$463
includes taxes & fees
21 Oct - 22 Oct
The Chester Hotel
A row of brick buildings with storefronts, including a bakery and a liquor store.

7. 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, (207 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is S$440
includes taxes & fees
7 Nov - 8 Nov
Maverick Suites at 245 Newbury St
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

8. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (435 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is S$322
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 28 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.

9. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (42 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 S$1,399
includes taxes & fees
25 Oct - 26 Oct
The Monty Boston
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

10. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (28 reviews)
"Cute space! Wasn’t too difficult navigating Boston from this location."
United States
Rebecca
The price is S$483
includes taxes & fees
27 Oct - 28 Oct
The Concord Hotel
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

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Resort was very clean and well maintained. Parking was close and easily accessible.Room was spacious and well decorated with modern amenities and the large window gave a great view of the city. Power curtains, Alexa operated lights and TV, a tablet to conveniently control the room. Staff was attentive and helpful. The Casino had numerous table games, sports betting and slot machines. We are from out of state but would not hesitate to return if in the area."
David 2-night trip
Posted 13 hours ago
Encore Boston Harbor

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.