Winthrop Vacation Rentals from $163: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Winthrop?

Spacious, New Renovation | Near T : This vacation home rental near Winthrop is equipped with a barbecue grill, 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 you can cook with friends or family.

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Our top choices for Winthrop vacation rentals

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Winthrop

Jeffrey V.

$369 nightly

Apr 5 - Apr 6

Total with taxes and fees

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

Charlestown

Jennifer E.

$454 nightly

Apr 14 - Apr 15

Total with taxes and fees

Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

South End

Yanmarie

$351 nightly

Apr 6 - Apr 7

Total with taxes and fees

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Downtown Boston

Junhu

$175 nightly

Apr 6 - Apr 7

Total with taxes and fees

Prime Central 1brm in North End Boston

North End

Taye A.

$309 nightly

Apr 6 - Apr 7

Total with taxes and fees

Blissful South End Studio

Back Bay

Penelope D.

$188 nightly

Apr 5 - Apr 6

Total with taxes and fees

3BR pet-friendly Quincy house w/parking — near Adams Park

Quincy

Stefanie K.

$348 nightly

Apr 5 - Apr 6

Total with taxes and fees

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

Fenway–Kenmore

Mai

$199 nightly

Apr 5 - Apr 6

Total with taxes and fees

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Top Winthrop Hotel Reviews

Arcadian Hotel

10/10 Excellent

"Great hotel, friendly & accommodating staff. I would definitely stay here again! "

Harborside Inn Of Boston

10/10 Excellent

"We had an enjoyable experience. Room was nice, bed was comfortable, shower worked great. They have a vcr and dvd player in the room with a bookshelf full of movies to choose from (located downstairs). My only complaint was they do not have bags/liners for the ice bucket. Easy walk to Quincy Market, the ferry, tours, etc. overall, it was pleasant and we would definitely stay here again. "

citizenM Boston North Station

10/10 Excellent

"This was the most beautiful, aesthetically pleasing hotel I have ever stayed in, no lie! The rooms are very modern and upscale with a nice view. The whole layout of the hotel, from the cafe, to the book shelves (which was the best part) and the bar was very nice. Using the ipad to remote control everything in the room, including the curtains and shower was fantastic. My doctors are in Boston, so I will routinely need to travel to Boston to make my appts. I have already decided to make this hotel my getaway spot. Thank you for a really nice stay!!"

The Midtown Hotel MOD Collection by Sonesta

6/10 Okay

"I really liked this hotel and location. My only "complaint" would be that there was no way to control the air temperature in the room. I like to sleep a bit cooler and it was hot. No ventilation and only opening the window were options. Also, there were stairs from the lobby to the hall to the elevator which is hard with heavy bags. Hot water seemed to be finicky as well. Very clean rooms, all newly renovated, had a hand steamer for my clothes which worked good, and a spot off the floor to put my suitcase. Could have used a little more sink space. "

Find out more about Winthrop

Everything you need to know about Winthrop vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winthrop in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $163 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop vacation 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 vacation.

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.

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Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals where you'll be only 3.7 mi (6 km) from New England Aquarium, giving you 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 cafes and waterfront during your trip.

What are some of the best vacation home rentals in Winthrop?

Spacious, New Renovation | Near T: This vacation home rental near Winthrop is equipped with a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals are there in Winthrop?

With 4 Expedia vacation rentals, you're sure 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 vacation rentals like in Winthrop?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Winthrop. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.

Winthrop Vacation Rentals

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Our top choices for Winthrop vacation rentals

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

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

The Chester Hotel

Temple Place Suites

Prime Central 1brm in North End Boston

Blissful South End Studio

3BR pet-friendly Quincy house w/parking — near Adams Park

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

3BR3Bth Entire House/Steps to Downtown & TD Garden

Gorgeous Beacon Hills Studio next to State house

Primo North End Studio

Hocus Pocus Season is here! Don’t miss it!

Village Colonial / Harbor Views.

Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly

1 Mi to Downtown: Salem Vacation Rental!

North End Entire House

Maverick Suites at 40 Temple St

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Exquisite North End 1brm

*New Spooky Halloween 2BR|Salem|Walking Downtown

Find vacation rentals that suit your style

Top Winthrop Hotel Reviews

Arcadian Hotel

Find out more about Winthrop

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