Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Winthrop vacation rentals

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, (631 reviews)
"Great location, Central to all main attractions and great restaurants, food, entertainment. Custom house is fantastic building rich in history. Great place to stay in Boston "
Australia
Antonios
The price is P17,259
P19,839 total
includes taxes & fees
May 25 - May 26
Marriott Vacation Club® at Custom House, Boston
Exterior

The Warlock House

The Warlock House
3.0 star property
Salem
The price is P55,635
P83,620 total
includes taxes & fees
Jun 3 - Jun 4
The Warlock House
2 bedrooms, desk

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
Coastal Charm Lobster Ch Teau
Interior

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
6.0 out of 10, (2 reviews)
The price is P18,083
P29,300 total
includes taxes & fees
May 22 - May 23
Furnished Apartment near BMC
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 P10,183
P25,458 total
includes taxes & fees
May 28 - May 29
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
Front of property

Symple Live

Symple Live
4.0 star property
Fenway–Kenmore
The price is P12,775
P20,716 total
includes taxes & fees
May 24 - May 25
Symple Live
Living area

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (32 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is P10,225
P19,561 total
includes taxes & fees
May 22 - May 23
The Chester Hotel
1 bedroom, desk, laptop workspace, free WiFi

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.6 out of 10, Excellent, (14 reviews)
"Nice spot"
United States
Kimberly
The price is P14,565
P23,163 total
includes taxes & fees
May 22 - May 23
Furnished Apartments near Encore Boston
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,200 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
The price is P8,832
P9,865 total
includes taxes & fees
May 25 - May 26
Crescent Suites Hotel
Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (693 reviews)
"Great location "
Canada
Robert
The price is P9,338
P17,828 total
includes taxes & fees
May 25 - May 26
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, (282 reviews)
"This property was awesome. The unit was clean and the bed was comfortable. The location is within walking distance of many fun venues. The only thing not so great was the furniture in the living room - small couch and only one other chair. At check in we only got one key which made the first 2 days of our stay tricky - you need keys to get in and out of the building, into the elevator banks and to access the floor. With only one key we had to stay together or plan for one to stay back in...
United States
Jacqueline
The price is P11,911
P20,601 total
includes taxes & fees
May 25 - May 26
Kasa Boston at Fenway
5 bedrooms, desk

Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
2.0 star property
Stoneham
The price is P22,121
P48,701 total
includes taxes & fees
May 31 - Jun 1
Enchanting Hidden Door Escape
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, (150 reviews)
"The property is clean and for the money, is a win for the visitor. "
United States
Ramon S
The price is P7,332
P14,104 total
includes taxes & fees
May 24 - May 25
Maverick Suites at 400 Columbus Ave
Interior

1 Mi to Downtown: Salem Vacation Rental!

1 Mi to Downtown: Salem Vacation Rental!
3.0 star property
Salem
10.0 out of 10, Exceptional, (3 reviews)
"Great overall stay! "
United States
Tessa
The price is P7,159
P22,544 total
includes taxes & fees
May 26 - May 27
1 Mi to Downtown: Salem Vacation Rental!
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, (375 reviews)
"Wonderful stay， convenient location "
United States
Junhu
The price is P7,443
P12,458 total
includes taxes & fees
May 25 - May 26
Temple Place Suites
1 bedroom, iron/ironing board, free cribs/infant beds, rollaway beds

Apartments in Salem

Apartments in Salem
3.0 star property
Salem
8.0 out of 10, Very Good, (48 reviews)
"The whole floor was clean and organized. The whole floor also felt inviting and comforting. We enjoyed how close we where to everthing. We were both so happy with found this apartment. "
United States
Jason
The price is P18,515
P29,899 total
includes taxes & fees
May 25 - May 26
Apartments in Salem
Front of property

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (116 reviews)
"A phenomenal stay at maverick suites! The location was fantastic, the room was spotless and cozy, and the check-in/out process was a breeze. I’d happily stay here again and recommend to anyone taking a trip to Boston!"
United States
Kendra
The price is P8,332
P15,253 total
includes taxes & fees
May 22 - May 23
Maverick Suites at 40 Temple St
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, (168 reviews)
"Great place for a solo business trip. Great location"
United States
Eleazar
The price is P10,220
P17,424 total
includes taxes & fees
May 25 - May 26
Maverick Suites at 245 Newbury St
Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (212 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is P10,615
P22,844 total
includes taxes & fees
May 25 - May 26
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

The Dagny Boston

The Dagny Boston

10/10 Excellent
"Everything was very clean, from the lobby to the room which made us feel comfortable and relaxed right away. The check-in experience was amazing, the staff was welcoming, professional, and very kind. The hotel is located in a lovely area, close to many restaurants, shops, and attractions, which made it very convenient for us. The room was spacious, comfortable, and well maintained, and overall the atmosphere of the hotel was warm and pleasant. We truly enjoyed our experience and would definitely stay here again. Highly recommended!"
Luana 1-night trip
Posted 1 hour ago
The Dagny Boston

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals where you'll be only 3.7 mi (6 km) from New England Aquarium, giving you 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 cafes and waterfront during your trip.

How many vacation rentals are there in Winthrop?

With 5 Expedia vacation rentals, you're sure 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 Fenway Park and Boston Harbor.

What are vacation rentals like in Winthrop?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Winthrop. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.