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Winthrop Holiday Rentals

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Check prices for these dates

Tonight
12 Dec - 13 Dec
Tomorrow
13 Dec - 14 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Winthrop holiday rentals

Front of property
Maverick Suites at 28 Fenway

Apartment in Fenway–Kenmore

Maverick Suites at 28 Fenway
3.0 star property
8.8 out of 10, Excellent, (325)
"Good place"
United States
Elijah
The price is HK$676
HK$1,538 total
includes taxes & fees
12 Jan - 13 Jan 2026
Maverick Suites at 28 Fenway
Desk, iron/ironing board, free WiFi, bed sheets
Temple Place Suites

Apartment in Downtown Boston

Temple Place Suites
2.5 star property
7.0 out of 10, Good, (325)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is HK$700
HK$1,297 total
includes taxes & fees
18 Dec - 19 Dec
Temple Place Suites
Lobby lounge
Global Luxury Suites Downtown Boston

Aparthotel in Chinatown

Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (629)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
Global Luxury Suites Downtown Boston
Exterior
Maverick Suites at 245 Newbury St

Aparthotel in Back Bay

Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (154)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St
Interior entrance
Maverick Suites at 89 Marion

Aparthotel in Coolidge Corner South Side

Maverick Suites at 89 Marion
2.0 star property
8.2 out of 10, Very good, (270)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
Maverick Suites at 89 Marion
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village

Aparthotel in Bay Village

Premier Suites - Bay Village
2.0 star property
6.4 out of 10, (251)
"Clean room, good location, check in check out easily!"
United States
HIEN T
Premier Suites - Bay Village
Terrace/patio
Crescent Suites Hotel

Aparthotel in South Side

Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (1143)
"Lovely, quiet place."
United States
Fatu
Crescent Suites Hotel
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites

Aparthotel in Bay Village

Bay Village Suites
2.0 star property
6.4 out of 10, (250)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Front of property
Maverick Suites at 40 Temple St

Aparthotel in Beacon Hill

Maverick Suites at 40 Temple St
2.0 star property
7.6 out of 10, Good, (102)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
Maverick Suites at 40 Temple St
Living area
The Monty Boston

Aparthotel in Downtown Boston

The Monty Boston
2.5 star property
9.4 out of 10, Exceptional, (28)
"Amazing property, would stay again."
United States
Doug
The price is HK$4,364
HK$6,357 total
includes taxes & fees
16 Dec - 17 Dec
The Monty Boston
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Aparthotel in South End

Maverick Suites at 400 Columbus Ave
2.0 star property
7.4 out of 10, Good, (133)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
Maverick Suites at 400 Columbus Ave
Exterior
Maverick Suites at 402 Columbus Ave

Aparthotel in South End

Maverick Suites at 402 Columbus Ave
2.5 star property
7.8 out of 10, Good, (68)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 Columbus Ave
Indoor pool, pool umbrellas, pool loungers
Global Luxury Suites East Boston

Aparthotel in East Boston

Global Luxury Suites East Boston
4.0 star property
6.8 out of 10, (176)
"The place was very nice and nicely equipped, but a little difficult to locate."
United States
William
The price is HK$1,090
HK$1,602 total
includes taxes & fees
29 Dec - 30 Dec
Global Luxury Suites East Boston
Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites

Aparthotel in Fenway–Kenmore

Charlesgate Suites
3.5 star property
9.4 out of 10, Exceptional, (201)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is HK$1,338
HK$2,880 total
includes taxes & fees
15 Dec - 16 Dec
Charlesgate Suites
Living area
The Chester Hotel

Aparthotel in South End

The Chester Hotel
4.0 star property
8.6 out of 10, Excellent, (28)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is HK$1,165
HK$2,726 total
includes taxes & fees
22 Dec - 23 Dec
The Chester Hotel
Billiards
Luxury Apartments by Hyatus at Boston Everett

Apartment in Everett

Luxury Apartments by Hyatus at Boston Everett
3.0 star property
10.0 out of 10, Exceptional, (1)
"Honestly this was one of the best furnished apartments I’ve ever stayed in, and I travel a lot for work. My partner and I came with another couple and we all kept saying how we wished we had booked a few extra nights. The place was super clean, modern, and honestly way bigger than we expected lol. First night we accidentally got the wrong door code but the host fixed it in like two minutes which was amazing. The living room became our hangout spot every evening and we even cooked dinner together...
United States
Yitzy
Luxury Apartments by Hyatus at Boston Everett
Exterior
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

Condo in Downtown Salem

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!
9.6 out of 10, Exceptional, (61)
"Amazing place to stay! Love the attention to decorating details, from the spooky lighting to the Alexa “Scroll of Spells” and it’s within close walking distance to many Salem attractions! Would recommend to anyone!"
United States
More M.
The price is HK$2,552
HK$6,021 total
includes taxes & fees
16 Dec - 17 Dec
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!
Interior
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Holiday Home in South Boston

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
9.8 out of 10, Exceptional, (182)
"Great home with everything you need for an awesome stay. "
United States
Lisa B.
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Fridge, microwave, oven, stovetop
Modern 2 BR, 1BA Near Convention Center & Seaport

Apartment in South Boston

Modern 2 BR, 1BA Near Convention Center & Seaport
9.8 out of 10, Exceptional, (201)
"The apartment and location were excellent. We loved how convenient it was to access all the attractions."
United States
Monica B.
Modern 2 BR, 1BA Near Convention Center & Seaport
1 bedroom, iron/ironing board, free cots/infant beds, rollaway beds
Apartments in Salem

Apartment in Salem

Apartments in Salem
3.0 star property
8.0 out of 10, Very good, (48)
"Property was fine. It is well located to see the sites in Salem. Only negative was that the neighbors were a bit loud at night. "
United States
Wes
Apartments in Salem
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
"The coffee was fantastic, the scones were to die for and the yogurt parfaits were delicious. We stayed in two different rooms. They were both impeccably clean. The hotel has a boutique vibe and my wife and I loved it. We will definitely be back when we visit Boston again. Thank you for a great stay! "
Jack 1-night trip
Posted 2 hours 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:

  • 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!

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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.

What are some of the best holiday rentals that Winthrop has to offer?

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi: This holiday home rental outside of Winthrop is located in the city centre, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Winthrop?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

Boston Harbor Islands State Park and Winthrop 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 New England Aquarium.

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.