Winthrop Holiday Rentals

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Our top choices for Winthrop holiday rentals

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, (630 reviews)
"Beautiful hotel and easy access to everything."
United States
Kimberely
The price is NZ$644
includes taxes & fees
9 May - 10 May
Marriott Vacation Club® at Custom House, Boston

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is NZ$1,032
includes taxes & fees
7 May - 8 May
Coastal Charm Lobster Ch Teau

The Warlock House

The Warlock House
3.0 star property
Salem
The price is NZ$1,674
includes taxes & fees
7 May - 8 May
The Warlock House

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 NZ$699
includes taxes & fees
9 May - 10 May
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is NZ$716
includes taxes & fees
6 May - 7 May
The Chester Hotel

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,182 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
The price is NZ$271
includes taxes & fees
7 May - 8 May
Crescent Suites Hotel

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (36 reviews)
"Excellent location, very easy check in process, clean, just as the pictures showed online."
United States
shannon
The price is NZ$1,644
includes taxes & fees
6 May - 7 May
The Monty Boston

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (689 reviews)
"Great staff, clean, and location"
United States
Juan
The price is NZ$365
includes taxes & fees
10 May - 11 May
Global Luxury Suites Downtown Boston

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 NZ$565
includes taxes & fees
6 May - 7 May
Furnished Apartments near Encore Boston

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (112 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 NZ$538
includes taxes & fees
9 May - 10 May
Maverick Suites at 40 Temple St

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (210 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is NZ$685
includes taxes & fees
6 May - 7 May
Charlesgate Suites

Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
2.0 star property
Stoneham
The price is NZ$1,217
includes taxes & fees
18 May - 19 May
Enchanting Hidden Door Escape

Rockmere Inn

Rockmere Inn
3.5 star property
Marblehead Historic District
Rockmere Inn

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, (165 reviews)
"Great location. Well priced. Its appeals to a specific type of traveler. Overall clean, quiet, solid WiFi services. I had some initial challenges getting in the building, but that was my fault for not checking in and providing the required documents. I would definitely stay again. PS The pizza place right across the street makes a great thin crust pie. "
United States
James
The price is NZ$524
includes taxes & fees
10 May - 11 May
Maverick Suites at 245 Newbury St

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (144 reviews)
"Great location!"
United States
Kevin
The price is NZ$438
includes taxes & fees
6 May - 7 May
Maverick Suites at 400 Columbus Ave

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (357 reviews)
"Great stay. "
United States
Anna
The price is NZ$510
includes taxes & fees
6 May - 7 May
Maverick Suites at 28 Fenway

Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
9.0 out of 10, Wonderful, (11 reviews)
"Great property. Very clean and spacious. Easy 15 minutes walk to Harvard. Easy check in and check out process"
United States
Tho
The price is NZ$678
includes taxes & fees
6 May - 7 May
Furnished Apts near Harvard Stadium

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 NZ$619
includes taxes & fees
13 May - 14 May
1 Mi to Downtown: Salem Vacation Rental!

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 NZ$688
includes taxes & fees
7 May - 8 May
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

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, 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 NZ$271 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?

Centrally located in the heart of Boston near T: This holiday home rental outside of Winthrop has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 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 5 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 Massachusetts Bay 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.