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

Search Holiday Rentals in Winthrop

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 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, (681 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 Rp4.105.299
Rp4.719.041 total
includes taxes & fees
22 Nov - 23 Nov
Marriott Vacation Club® at Custom House, Boston
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

2. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (215 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is Rp2.240.902
Rp4.654.443 total
includes taxes & fees
6 Dec - 7 Dec
Global Luxury Suites East Boston
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

3. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (772 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is Rp1.866.423
Rp4.280.777 total
includes taxes & fees
6 Dec - 7 Dec
Global Luxury Suites Downtown Boston
A modern hotel room with a large bed, a sofa, a small table, and a view of the city.

4. Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.4 out of 10, Very good, (24 reviews)
"Several items were broken, damaged, or in disrepair upon arrival. An elevator alarm was ringing for at least 16 hours before being resolved late at night. Check in and check out process needs to be more clear and streamlined."
United States
Gina
Furnished Apartments near Encore Boston
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

5. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (474 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is Rp1.855.213
Rp3.899.314 total
includes taxes & fees
7 Dec - 8 Dec
Maverick Suites at 28 Fenway
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

6. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,350 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
The price is Rp2.750.272
Rp3.072.053 total
includes taxes & fees
7 Dec - 8 Dec
Crescent Suites Hotel
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, (44 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
The price is Rp2.604.816
Rp5.281.499 total
includes taxes & fees
8 Nov - 9 Nov
The Chester Hotel
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, (348 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is Rp3.254.760
Rp5.368.727 total
includes taxes & fees
7 Dec - 8 Dec
Kasa Boston at Fenway
A room with a white door, a white table with a chair, and a red light on the wall.

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, (166 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 Rp2.051.293
Rp4.021.427 total
includes taxes & fees
1 Dec - 2 Dec
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
8.4 out of 10, Very good, (219 reviews)
"Great location - plenty to do."
United States
Chloe
The price is Rp2.051.293
Rp4.021.427 total
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 245 Newbury St
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

11. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (553 reviews)
"We will definitely stay here again!"
United States
James
The price is Rp1.627.380
Rp3.013.863 total
includes taxes & fees
7 Dec - 8 Dec
Temple Place Suites
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

12. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (398 reviews)
"Good place to stay."
United States
Jaetaek
The price is Rp1.530.329
Rp2.694.812 total
includes taxes & fees
23 Nov - 24 Nov
Premier Suites - Bay Village
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.

13. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (48 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 Rp12.538.029
Rp17.531.497 total
includes taxes & fees
20 Nov - 21 Nov
The Monty Boston
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

14. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (39 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is Rp2.897.858
Rp5.618.443 total
includes taxes & fees
22 Nov - 23 Nov
The Concord Hotel
A wooden hallway with a patterned floor leading to a door.

15. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (355 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is Rp1.855.213
Rp3.688.081 total
includes taxes & fees
7 Dec - 8 Dec
Maverick Suites at 89 Marion
A modern hotel room with a bed, a desk, a sofa, and a dining area.

16. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (246 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is Rp3.111.308
Rp6.695.462 total
includes taxes & fees
23 Nov - 24 Nov
Charlesgate Suites
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.

17. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (186 reviews)
"Very well located. Close to two subways and Copeland Square."
Canada
Lorne
The price is Rp1.855.213
Rp3.795.387 total
includes taxes & fees
7 Dec - 8 Dec
Maverick Suites at 400 Columbus Ave
A hotel room with a bed, a desk, a lamp, a potted plant, and large windows with blinds.

18. Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
5.6 out of 10, (4 reviews)
"I loved this apartment. It was perfect for what we needed. I only gave four stars because the apartment could use a little love and updating, and that may be important to some people. It was not for me. We were just over 2 miles away from Mass General where my husband was having an operation. It had a full kitchen, 1 1/2 baths, and was surprisingly quiet. The description of the apartment was clear there was no parking space associated with the apartment; however, I found that every night...
United States
Christine
The price is Rp2.800.177
Rp5.714.000 total
includes taxes & fees
8 Nov - 9 Nov
Furnished Apartment near BMC
A hotel room with a large bed, two bedside lamps, a headboard, a wall-mounted abstract art piece, and potted plants.

19. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
8.2 out of 10, Very good, (17 reviews)
"Great location, easy to access, and quick to respond to questions"
United States
ANITA
The price is Rp2.010.592
Rp4.670.481 total
includes taxes & fees
8 Nov - 9 Nov
Furnished Apartment Near Longwood
A modern living room with a sofa, a dining table, and a kitchen area with appliances.

20. Luxury 2BR near Cambridge

Luxury 2BR near Cambridge
3.0 star property
Prospect Hill
6.6 out of 10, (7 reviews)
"Excellent location. Clean,"
Canada
Carrie-Anne
The price is Rp2.315.392
Rp5.010.942 total
includes taxes & fees
8 Nov - 9 Nov
Luxury 2BR near Cambridge
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Hotel Reviews

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"The experience at the Omni was wonderful. The hotel is beautiful with an outstanding staff. They were very professional and courteous - from the front desk to the bell boy. There are a few restaurants to choose from and several amenities. Highly recommend."
Stella 3-night trip
Posted less than an hour ago
Omni Boston Hotel at the Seaport

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia.co.id! 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.