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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winthrop holiday rentals

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

1. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (473 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is Rp1.933.302
Rp3.344.721 total
includes taxes & fees
20 Sept - 21 Sept
Temple Place Suites
Rooftop terrace

2. 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, (666 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is Rp8.734.476
Rp10.040.280 total
includes taxes & fees
20 Sept - 21 Sept
Marriott Vacation Club® at Custom House, Boston
42-inch TV with satellite channels

3. 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 Rp2.588.387
Rp4.607.918 total
includes taxes & fees
20 Sept - 21 Sept
Maverick Suites at 400 Columbus Ave
Front of property

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, (146 reviews)
"Worth the stay"
Canada
Akansha
The price is Rp3.177.317
Rp5.279.650 total
includes taxes & fees
21 Sept - 22 Sept
Maverick Suites at 40 Temple St
Lobby

5. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (317 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 Rp2.485.420
Rp2.856.990 total
includes taxes & fees
20 Sept - 21 Sept
Kasa Boston at Fenway
Premium Apartment | Living area | 24-inch Smart TV with digital channels

6. 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 Rp3.451.183
Rp6.211.913 total
includes taxes & fees
20 Sept - 21 Sept
The Chester Hotel
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

7. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (344 reviews)
"Location is great"
United States
Eria
The price is Rp2.045.146
Rp3.269.212 total
includes taxes & fees
20 Sept - 21 Sept
Premier Suites - Bay Village
Indoor pool, pool umbrellas, pool loungers

8. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (210 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is Rp4.681.466
Rp7.422.053 total
includes taxes & fees
20 Sept - 21 Sept
Global Luxury Suites East Boston
Exterior

9. 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, (203 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is Rp2.192.939
Rp4.153.351 total
includes taxes & fees
20 Sept - 21 Sept
Maverick Suites at 245 Newbury St
Lobby lounge

10. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (745 reviews)
"Friendly sat at Front and the property is very nice it was useful for a quick work trip. Easy to get around well lit and maintained"
United States
Christopher
The price is Rp5.766.352
Rp8.842.120 total
includes taxes & fees
30 Sept - 1 Oct
Global Luxury Suites Downtown Boston
Front of property

11. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (424 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is Rp3.179.562
Rp5.389.508 total
includes taxes & fees
20 Sept - 21 Sept
Maverick Suites at 28 Fenway
Studio | Iron/ironing board, free WiFi

12. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (23 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 Rp3.483.139
Rp6.248.647 total
includes taxes & fees
20 Sept - 21 Sept
The Concord Hotel
Apartment (1 Bedroom) | Interior

13. Apt in Historic Lynn Neighborhood: 5 Mi to Salem!

Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
3.0 star property
Lynn
The price is Rp2.654.400
Rp6.592.645 total
includes taxes & fees
27 Sept - 28 Sept
Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services

14. 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 Rp8.903.129
Rp13.295.208 total
includes taxes & fees
29 Sept - 30 Sept
The Monty Boston
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

15. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (236 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is Rp3.603.859
Rp7.203.812 total
includes taxes & fees
21 Sept - 22 Sept
Charlesgate Suites
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

16. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (22 reviews)
"Great location, close to the T line, grocery store nearby. Clean, quiet and very comfortable accommodations, especially the best bed I’ve slept in at a rental location. Had everything we needed, looking forward to coming back!"
United States
Lori
The price is Rp7.971.097
Rp11.101.447 total
includes taxes & fees
20 Sept - 21 Sept
Symple Live
30-inch flat-screen TV with satellite channels, TV

17. Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
8.0 out of 10, Very good, (87 reviews)
"It was very close to stores to go shopping and amazing spot to get last minute reservations for dinner"
United States
Talyciah
The price is Rp2.516.487
Rp4.525.270 total
includes taxes & fees
28 Sept - 29 Sept
Maverick Suites at 402 Columbus Ave
Interior entrance

18. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (312 reviews)
"Stayed in the economy suite, very suitable for a couple! Very clean room and I have never had an easier check-in process!!"
United States
Paula
The price is Rp2.185.898
Rp4.022.963 total
includes taxes & fees
20 Sept - 21 Sept
Maverick Suites at 89 Marion
Apartment | Interior

19. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
7.6 out of 10, Good, (7 reviews)
"Easy to check in, students friendly apartment, convenient location, easy to call Uber or Lyft, and within 20 min. drive to the famous universities."
United States
Sujiang
The price is Rp2.523.678
Rp5.198.562 total
includes taxes & fees
20 Sept - 21 Sept
Furnished Apartment Near Longwood
Terrace/patio

20. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,273 reviews)
"Great location, close to restaurants and stores. Beautiful rooms. Close enought to Boston without all the traffic. Close to Mass Pike."
United States
Mark
The price is Rp2.860.008
Rp3.194.628 total
includes taxes & fees
20 Sept - 21 Sept
Crescent Suites 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.
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

Lakeside Inn

Lakeside Inn

10/10 Excellent
"Nice survey"
Zehan 1-night trip
Posted 5 hours ago
Lakeside Inn

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 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.