Winthrop Holiday Rentals from €142: Search Short-Term Rentals

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Our top choices for Winthrop holiday rentals

1. Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Winthrop

Kristie P.

includes taxes & fees

17 Sept - 18 Sept

2. Casa de Los Clarey • Boston • Logan • Beaches • Free Parking

Winthrop

"Had a great stay here! Had a little issue at check in, and Frankie immediately responded to my phone call. Considering the quick response and resolution, I wouldn't hesitate to stay at any of his properties again! Nice location and definitely take him up on his restaurant recommendations... we tried out Jac's for breakfast and it was phenomenal and by far the least expensive meal on our entire trip. The house is a bit ran down in areas and doesn't feel super secure, but it is overall a very cool...

Stacy B.

includes taxes & fees

1 Sept - 2 Sept

3. Beautiful 3-bedroom apartment with AC in welcoming Winthrop

Winthrop

includes taxes & fees

1 Sept - 2 Sept

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

Charlestown

Angela L.

includes taxes & fees

7 Sept - 8 Sept

5. Fun houseboat. Walk to Boston attractions WIFI

Boston

William M.

includes taxes & fees

31 Aug - 1 Sept

6. Your Floating Suite in Boston Harbor

Thompson Square - Bunker Hill

Kelly H.

includes taxes & fees

31 Aug - 1 Sept

7. Gorgeous Beacon Hills Studio next to State house

Beacon Hill

Robin P.

includes taxes & fees

20 Sept - 21 Sept

8. The Concord Hotel

South End

Cotie

includes taxes & fees

31 Aug - 1 Sept

9. Marriott Vacation Club® at Custom House, Boston

Downtown Boston

Brittany

includes taxes & fees

2 Sept - 3 Sept

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

10. Temple Place Suites

Downtown Boston

Hunter

includes taxes & fees

31 Aug - 1 Sept

11. Maverick Suites at 40 Temple St

Beacon Hill

Akansha

includes taxes & fees

31 Aug - 1 Sept

12. Kasa Boston at Fenway

Fenway–Kenmore

MARLYN

includes taxes & fees

7 Sept - 8 Sept

13. Perfetto North End 1brm

North End

Deborah S.

includes taxes & fees

14 Sept - 15 Sept

14. Amazing price and location / parking -North End (M1S)

North End

Michael

15. Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Downtown Boston

Rachael M.

includes taxes & fees

12 Sept - 13 Sept

16. Modern North End Studio

North End

James

includes taxes & fees

6 Sept - 7 Sept

1 bedroom, desk, iron/ironing board, WiFi

17. Perfect One Bedroom Stay In Downtown Boston!

Downtown Boston

Keith

includes taxes & fees

7 Sept - 8 Sept

18. The Chester Hotel

South End

Shanida

includes taxes & fees

8 Sept - 9 Sept

Coffee/tea maker, fridge, microwave, oven

19. 3BR3Bth Entire House/Steps to Downtown & TD Garden

North End

Erin A.

includes taxes & fees

31 Aug - 1 Sept

20. Sleek Studio Apartment in the South End

Back Bay

Unspecified U.

includes taxes & fees

3 Sept - 4 Sept

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Top Winthrop Hotel Reviews

Hilton Boston Park Plaza

10/10 Excellent

"We stay here all the time to move daughter into Emerson, always a great experience"

citizenM Boston Back Bay

10/10 Excellent

"This is the first time staying at one of these properties, but I would do it again in a heartbeat. The room was small, but modern and comfortable. I loved having the bed up against a huge window looking out over the city - a nice touch. The self-check in was new to me, but it was fast and easy. The food at the the rooftop bar was incredible. All and all, I'll definitely be staying here again, and I will look for the same property in other cities going forward if traveling solo."

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 €142 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?

Boston's Best Vacation Home : This holiday home rental outside of Winthrop is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay.

How many holiday rentals are there in Winthrop?

With 6 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 TD Garden and Fenway Park.

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

1. Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

2. Casa de Los Clarey • Boston • Logan • Beaches • Free Parking

3. Beautiful 3-bedroom apartment with AC in welcoming Winthrop

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