Winthrop Holiday Rentals from €141: Search Short-Term Rentals

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Our top choices for Winthrop holiday rentals

A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

1. Marriott Vacation Club® at Custom House, Boston

Downtown Boston

Brittany

includes taxes & fees

31 Oct - 1 Nov

A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

2. Global Luxury Suites East Boston

East Boston

Erica

includes taxes & fees

9 Nov - 10 Nov

A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

3. Global Luxury Suites Downtown Boston

Chinatown

Myah

includes taxes & fees

10 Nov - 11 Nov

An outdoor patio with round tables and chairs, surrounded by green umbrellas.

4. Crescent Suites Hotel

South Side

kari

includes taxes & fees

31 Oct - 1 Nov

A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

5. The Chester Hotel

South End

Luda

includes taxes & fees

3 Nov - 4 Nov

A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

6. Maverick Suites at 28 Fenway

Fenway–Kenmore

Beenish

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

7. Kasa Boston at Fenway

Fenway–Kenmore

Kelly

includes taxes & fees

4 Nov - 5 Nov

A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

8. Maverick Suites at 40 Temple St

Beacon Hill

TommyWallace

includes taxes & fees

1 Nov - 2 Nov

A row of brick buildings with storefronts, including a bakery and a liquor store.

9. Maverick Suites at 245 Newbury St

Back Bay

Jennifer

includes taxes & fees

9 Nov - 10 Nov

A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

10. Temple Place Suites

Downtown Boston

Deborah

includes taxes & fees

3 Nov - 4 Nov

A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

11. The Concord Hotel

South End

Carla Patricia

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with a central island, a dining area with a round table and chairs, and a large window providing a view of the city at night.

12. The Monty Boston

Downtown Boston

Jodi

includes taxes & fees

25 Oct - 26 Oct

A modern bedroom with a large bed, a fireplace, and two windows with blinds.

13. Premier Suites - Bay Village

Bay Village

Rosemary

includes taxes & fees

9 Nov - 10 Nov

A wooden hallway with a patterned floor leading to a door.

14. Maverick Suites at 89 Marion

Coolidge Corner

Katerina

includes taxes & fees

15 Nov - 16 Nov

A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

15. Maverick Suites at 400 Columbus Ave

South End

Evelyn

includes taxes & fees

9 Nov - 10 Nov

A hotel room with a bed, a desk, a lamp, a potted plant, and large windows with blinds.

16. Furnished Apartment near BMC

South End

"I loved this apartment. It was perfect for what we needed. I only gave four stars because the apartment could use a little love and updating, and that may be important to some people. It was not for me. We were just over 2 miles away from Mass General where my husband was having an operation. It had a full kitchen, 1 1/2 baths, and was surprisingly quiet. The description of the apartment was clear there was no parking space associated with the apartment; however, I found that every night...

Christine

A modern hotel room with a bed, a desk, a sofa, and a dining area.

17. Charlesgate Suites

Fenway–Kenmore

Ana

includes taxes & fees

3 Nov - 4 Nov

A hotel room with a large bed, two bedside lamps, a headboard, a wall-mounted abstract art piece, and potted plants.

18. Furnished Apartment Near Longwood

North Brookline

Mike Shang-Yu

A modern living room with a round dining table, grey sofas, and large windows offering city views.

19. Furnished Apts near Harvard Stadium

Allston

Gregory

20. Symple Live

Fenway–Kenmore

Erica

includes taxes & fees

15 Nov - 16 Nov

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Top Winthrop Hotel Reviews

The Revolution Hotel

8/10 Good

"Second time staying here - was in a double room last time with a friend and that was great - the single room very tight - the sink too small to really use without getting water all over. no chair or luggage rack. Clean and sparse. Liked that they had a small gym downstairs. Nice area & close to Boston Common."

The Midtown Hotel MOD Collection by Sonesta

8/10 Good

"On te good side: Very clean, large and modern (well refreshed) room. The bed super ok. The zone is good as well. The one first lady was very helpful, the other people on staff, they are ok but it could be better. On the so-so side: That was not a breakfast. On the airplane, the quality is better. Clearly they give it just to be on paper as marketing attraction. Just don’t wake up early for that, it’s not worth it. Some noise during the night from the pipes, I assume is as much as you could change on that building. Overall, except the breakfast it’s a good choice."

Hyatt Regency Boston

10/10 Excellent

"We loved our stay here. It is right down the block from the show we saw and felt safe walking to and from. Lots of little shops and restaurants near by. Our bonus gifts from being an Expedia member were a nice touch too. Staff went above and beyond, the room was lovely and I would not hesitate to stay here again!"

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 €141 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, there are holiday rentals close to the most popular sights in Winthrop, or you can select a more secluded option if you're looking for a relaxing stay. 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?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This holiday home rental outside of Winthrop offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

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 Donovan 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 Faneuil Hall Marketplace.

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. Marriott Vacation Club® at Custom House, Boston

2. Global Luxury Suites East Boston

3. Global Luxury Suites Downtown Boston

4. Crescent Suites Hotel

5. The Chester Hotel

6. Maverick Suites at 28 Fenway

7. Kasa Boston at Fenway

8. Maverick Suites at 40 Temple St

9. Maverick Suites at 245 Newbury St

10. Temple Place Suites

11. The Concord Hotel

12. The Monty Boston

13. Premier Suites - Bay Village

14. Maverick Suites at 89 Marion

15. Maverick Suites at 400 Columbus Ave

16. Furnished Apartment near BMC

17. Charlesgate Suites

18. Furnished Apartment Near Longwood

19. Furnished Apts near Harvard Stadium

20. Symple Live

Find holiday rentals that suit your style

Top Winthrop Hotel Reviews

The Revolution Hotel

Omni Boston Hotel at the Seaport

Encore Boston Harbor

Arcadian Hotel

citizenM Boston Back Bay

The Dagny Boston

The Godfrey Hotel Boston

The Midtown Hotel MOD Collection by Sonesta

Hyatt Regency Boston

Find out more about Winthrop

Frequently asked questions

Go further with the Expedia app

Holiday Rentals in Winthrop

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winthrop holiday rentals

1. Marriott Vacation Club® at Custom House, Boston

2. Global Luxury Suites East Boston

3. Global Luxury Suites Downtown Boston

4. Crescent Suites Hotel

5. The Chester Hotel

6. Maverick Suites at 28 Fenway

7. Kasa Boston at Fenway

8. Maverick Suites at 40 Temple St

9. Maverick Suites at 245 Newbury St

10. Temple Place Suites

11. The Concord Hotel

12. The Monty Boston

13. Premier Suites - Bay Village

14. Maverick Suites at 89 Marion

15. Maverick Suites at 400 Columbus Ave

16. Furnished Apartment near BMC

17. Charlesgate Suites

18. Furnished Apartment Near Longwood

19. Furnished Apts near Harvard Stadium

20. Symple Live

Find holiday rentals that suit your style

Top Winthrop Hotel Reviews

The Revolution Hotel

Find out more about Winthrop

Frequently asked questions

Go further with the Expedia app