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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, (623 reviews)
"Hotel is in the perfect area to go to Faneuil hall as well as to the north end everything’s in walking distance multiple restaurants you can eat high-end or very inexpensive fun time for all"
United States
Cathy
The price is £282
includes taxes & fees
29 Mar - 30 Mar
Marriott Vacation Club® at Custom House, Boston

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 £227
includes taxes & fees
27 Mar - 28 Mar
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

The Warlock House

The Warlock House
3.0 star property
Salem
The price is £652
includes taxes & fees
26 Mar - 27 Mar
The Warlock House

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is £483
includes taxes & fees
31 Mar - 1 Apr
Coastal Charm Lobster Ch Teau

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
6.0 out of 10, (1 review)
Furnished Apartment near BMC

3 bd 2 ba Unit

3 bd 2 ba Unit
3.0 star property
East Somerville
The price is £409
includes taxes & fees
26 Mar - 27 Mar
3 bd 2 ba Unit

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (35 reviews)
"The best stay ever "
United States
Edward
The price is £583
includes taxes & fees
29 Mar - 30 Mar
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, (672 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
Global Luxury Suites Downtown Boston

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (257 reviews)
"This is a convenient property, close to the T and the Common. You will need to be able to walk up some narrow stairs, and adjust to sharing a common bathroom. I met the owner while he was shoveling snow after the nor'easter, and he could not have been nicer! Great value for the money, fairly quiet and I would stay again."
United States
Louise
Bay Village Suites

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is £235
includes taxes & fees
1 Apr - 2 Apr
The Chester Hotel

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,162 reviews)
"Dana’s customer service was excellent and my stay was as well. I will definitely stay again in the future."
United States
Sean
Crescent Suites Hotel

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 £272
includes taxes & fees
29 Mar - 30 Mar
1 Mi to Downtown: Salem Vacation Rental!

Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
2.0 star property
Stoneham
The price is £597
includes taxes & fees
2 Apr - 3 Apr
Enchanting Hidden Door Escape

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (340 reviews)
"Great location for this property. Definitely a low frills sort of place but such a convenient location-within walking distance from the Amtrak station. Convenient to pretty much anywhere you want to get to in Boston. Easy walk to Boston Common, Newbury Street, Beacon Hill, North End. Management was very responsive when we checked in and noted there was an issue with the heat and we needed a few more towels and sheets for the sofa bed. Some great options for food really close by. It was nice...
United States
Mary Anne
The price is £140
includes taxes & fees
30 Mar - 31 Mar
Temple Place Suites

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 £251
includes taxes & fees
26 Mar - 27 Mar
Apartments in Salem

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, (160 reviews)
"Great location, clean and great 😌 "
United States
Catherine
Maverick Suites at 245 Newbury St

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (261 reviews)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is £169
includes taxes & fees
28 Mar - 29 Mar
Premier Suites - Bay Village

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (104 reviews)
"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

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (136 reviews)
"I couldn’t quite get the plug in stove to work. But overall it was an alright stay!!"
United States
Myah
Maverick Suites at 400 Columbus Ave
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, 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?

Spacious, New Renovation | Near T: This holiday home rental outside of Winthrop is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 6 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 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?

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.