Winthrop Holiday Rentals from €135: Search Short-Term Rentals

Q: 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.

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Our top choices for Winthrop holiday rentals

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Winthrop

Jeffrey V.

includes taxes & fees

22 Apr - 23 Apr

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Charlestown

Jennifer E.

includes taxes & fees

22 Apr - 23 Apr

Fun houseboat. Walk to Boston attractions WIFI

Boston

Tracey

includes taxes & fees

22 Apr - 23 Apr

Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown

Thompson Square - Bunker Hill

Kim H.

includes taxes & fees

22 Apr - 23 Apr

Blissful South End Studio

Back Bay

Penelope D.

includes taxes & fees

21 Apr - 22 Apr

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Fenway–Kenmore

Mai

includes taxes & fees

22 Apr - 23 Apr

The Chester Hotel

South End

Yanmarie

includes taxes & fees

22 Apr - 23 Apr

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up)

Temple Place Suites

Downtown Boston

Junhu

includes taxes & fees

22 Apr - 23 Apr

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Top Winthrop Hotel Reviews

Seaport Hotel Boston

10/10 Excellent

"Seaport Hotel was wonderful. The staff members were incredible kind and welcoming. The rooms were clean and the view from the room was amazing. "

Omni Parker House

10/10 Excellent

"Omni Parker House was a short walk from all of Boston’s major attractions and overall in a great location. The hotel staff was very friendly and kept that composure when they assured us that it was no big deal when we forgot our sunglasses in our car and needed the valet to go get it for us. The doorman, whose name we unfortunately did not catch, greeted us with a smile every time we walked in and out of the building. As for our room, it was clean and had a working AC unit which was crucial for us because it was very hot during our stay. Each day, the beds were nicely made and fresh towels were provided. We did not get the chance to eat at Parker’s restaurant or enjoy a drink at the bar, but we heard that both were nice and the Boston cream pies were to die for! "

The Midtown Hotel MOD Collection by Sonesta

8/10 Good

"Clean, comfortable room except that the room was exceptionally hot the second night - I believe the thermostat was not working. The breakfast is cafeteria breakfast - packaged muffins/pastries and boxed OJ - not exactly what I was expecting but there are plenty of cafes around."

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 €135 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 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 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 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.

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Check prices for these dates

Our top choices for Winthrop holiday rentals

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Fun houseboat. Walk to Boston attractions WIFI