Holiday Rentals in Winthrop

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Winthrop

Temple Place Suites

2.5 star property
Downtown Boston
7.0 out of 10, Good, (321)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is €140
includes taxes & fees
2 Dec - 3 Dec
Temple Place Suites

Maverick Suites at 28 Fenway

3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (321)
"Spotless room, spotless building, great staff, comfortable bed. "
United States
Patricia
The price is €180
includes taxes & fees
2 Dec - 3 Dec
Maverick Suites at 28 Fenway

Global Luxury Suites Downtown Boston

4.0 star property
Chinatown
8.0 out of 10, Very good, (626)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
The price is €189
includes taxes & fees
4 Dec - 5 Dec
Global Luxury Suites Downtown Boston

Crescent Suites Hotel

3.0 star property
South Side
9.6 out of 10, Exceptional, (1141)
"Lovely, quiet place."
United States
Fatu
Crescent Suites Hotel

Bay Village Suites

2.0 star property
Bay Village
6.4 out of 10, (248)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites

Premier Suites - Bay Village

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

Maverick Suites at 89 Marion

2.0 star property
Coolidge Corner South Side
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

Maverick Suites at 245 Newbury St

2.0 star property
Back Bay
8.2 out of 10, Very good, (152)
"Good location, clean and quiet. Only thing that could be improved on would be luggage storage before check in "
United States
Kristee
Maverick Suites at 245 Newbury St

The Monty Boston

2.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (28)
"Amazing property, would stay again."
United States
Doug
The price is €585
includes taxes & fees
2 Dec - 3 Dec
The Monty Boston

Maverick Suites at 40 Temple St

2.0 star property
Beacon Hill
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

Maverick Suites at 400 Columbus Ave

2.0 star property
South End
7.2 out of 10, Good, (132)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
Maverick Suites at 400 Columbus Ave

Global Luxury Suites East Boston

4.0 star property
East Boston
6.8 out of 10, (175)
"The place was very nice and nicely equipped, but a little difficult to locate."
United States
William
The price is €159
includes taxes & fees
29 Dec - 30 Dec
Global Luxury Suites East Boston

Maverick Suites at 402 Columbus Ave

2.5 star property
South End
8.0 out of 10, Very good, (67)
"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

Charlesgate Suites

3.5 star property
Fenway–Kenmore
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 €379
includes taxes & fees
14 Dec - 15 Dec
Charlesgate Suites

The Chester Hotel

4.0 star property
South End
8.6 out of 10, Excellent, (27)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is €389
includes taxes & fees
2 Dec - 3 Dec
The Chester Hotel

Furnished Apartments near Encore Boston

2.5 star property
Everett
8.4 out of 10, Very good, (8)
"Great place. Very clean. Great communication."
United States
Michele
The price is €188
includes taxes & fees
2 Dec - 3 Dec
Furnished Apartments near Encore Boston

Modern 2 BR, 1BA Near Convention Center & Seaport

South Boston
9.8 out of 10, Exceptional, (200)
"Great property, great location, great communication with the host. Walking distance to everything - seaport, convention center, so many fun spots on W. Broadway. We thoroughly enjoyed our stay! "
United States
Cynthia A.
Modern 2 BR, 1BA Near Convention Center & Seaport

On River/Harvard Sq. two blocks

2.0 star property
West Cambridge
8.2 out of 10, Very good, (29)
"Great place to stay! We loved our time there!"
United States
Melody
The price is €215
includes taxes & fees
23 Dec - 24 Dec
On River/Harvard Sq. two blocks

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

Downtown Salem
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 €664
includes taxes & fees
2 Dec - 3 Dec
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston

Beacon Hill
8.6 out of 10, Excellent, (164)
"We loved our stay. The place was a little difficult to find (in the dark). The location is such an easy walk to the T and lots of other activities. We hope to be back next year. "
United States
Suzanne D.
Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winthrop Hotel Reviews

Find out more about Winthrop

Everything you need to know about Winthrop holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winthrop holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winthrop holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winthrop. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winthrop holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winthrop holiday rentals we have selected for you start as low as €140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winthrop rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winthrop holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winthrop. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy Salem Getaway. Historic Home Near All the Sights: This holiday home rental outside of Winthrop offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Winthrop?

With 4 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.