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
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Winthrop holiday rentals

Living area

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is S$425
includes taxes & fees
12 Jul - 13 Jul
The Chester Hotel
2 bedrooms, desk

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is S$889
includes taxes & fees
15 Jul - 16 Jul
Coastal Charm Lobster Ch Teau
Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (402 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
The price is S$228
includes taxes & fees
13 Jul - 14 Jul
Temple Place Suites
Front of property

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.8 out of 10, Good, (128 reviews)
"Very quiet, great location. "
United States
Cole
The price is S$491
includes taxes & fees
12 Jul - 13 Jul
Maverick Suites at 40 Temple St
Rooftop terrace

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, (639 reviews)
"Excellent location and clean room with beautiful views. Very comfortable and convenient."
United States
Noelle
The price is S$479
includes taxes & fees
19 Jul - 20 Jul
Marriott Vacation Club® at Custom House, Boston
Iron/ironing board, free WiFi

The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (2 reviews)
"There was very little loud construction outside the window as well as in the building before 8:30 am. The place was cute and relatively clean. Owners gave us a discount for the noise"
United States
Sara
The price is S$497
includes taxes & fees
13 Jul - 14 Jul
The Concord Hotel
Interior

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
The price is S$508
includes taxes & fees
14 Jul - 15 Jul
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (6 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is S$496
includes taxes & fees
3 Aug - 4 Aug
Symple Live
Exterior

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, (181 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is S$564
includes taxes & fees
13 Jul - 14 Jul
Maverick Suites at 245 Newbury St
Free WiFi

Luxury 2BR near Cambridge

Luxury 2BR near Cambridge
3.0 star property
Prospect Hill
9.0 out of 10, Wonderful, (2 reviews)
"Great apartment but the building's main door was malfunctioning and we could only get in when a resident with a key entered/exited. Also the wifi didn't work. The provider sis not offer any support or compensation, otherwise this would have been a perfect stay."
United States
Yonatan
Luxury 2BR near Cambridge
Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (302 reviews)
"Great location and well maintained"
United States
EDDIE
The price is S$213
includes taxes & fees
13 Jul - 14 Jul
Premier Suites - Bay Village
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (383 reviews)
"Great stay. "
United States
Anna
The price is S$481
includes taxes & fees
13 Jul - 14 Jul
Maverick Suites at 28 Fenway
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (157 reviews)
"Great location!"
United States
Kevin
The price is S$449
includes taxes & fees
14 Jul - 15 Jul
Maverick Suites at 400 Columbus Ave
Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (717 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
The price is S$395
includes taxes & fees
30 Jul - 31 Jul
Global Luxury Suites Downtown Boston
Lobby

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (291 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is S$534
includes taxes & fees
9 Jul - 10 Jul
Kasa Boston at Fenway
1 bedroom, desk, laptop workspace, free WiFi

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.8 out of 10, Excellent, (19 reviews)
"Nice spot"
United States
Kimberly
The price is S$388
includes taxes & fees
9 Jul - 10 Jul
Furnished Apartments near Encore Boston
Interior

Boston Duplex w/ Foosball Table: 11 Mi to Downtown

Boston Duplex w/ Foosball Table: 11 Mi to Downtown
3.0 star property
Hyde Park
The price is S$678
includes taxes & fees
18 Jul - 19 Jul
Boston Duplex w/ Foosball Table: 11 Mi to Downtown
Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (218 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is S$599
includes taxes & fees
14 Jul - 15 Jul
Charlesgate Suites
Exterior

Seacity View

Seacity View
2.0 star property
Swampscott
7.0 out of 10, Good, (2 reviews)
"Beautiful house!"
United States
carla n
The price is S$1,058
includes taxes & fees
19 Jul - 20 Jul
Seacity View
Interior

Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
6.8 out of 10, (5 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 S$590
includes taxes & fees
10 Jul - 11 Jul
Furnished Apartment Near Longwood
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

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

8/10 Good
"Great location and clean rooms. Air conditioning was challenged for days in the high 90s. Would absolutely stay there again."
Brian 3-night trip
Posted 2 hours ago
The Midtown Hotel MOD Collection by Sonesta

Frequently asked questions

Can I find a holiday rental in Winthrop?

Yes, we give you a choice of holiday rentals where you'll be only 3.7 mi (6 km) from New England Aquarium, providing a more secluded option to escape the hustle and bustle. 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 Point Shirley Beach are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include TD Garden and Fenway Park.

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.