A coastal town with a prominent lighthouse on a hill, surrounded by houses and greenery.

Winthrop Holiday Rentals

Dates

November 2026

December 2026

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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

Joseph

includes taxes & fees

22 Nov - 23 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

6 Dec - 7 Dec

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

Yelitza

includes taxes & fees

6 Dec - 7 Dec

A modern hotel room with a large bed, a sofa, a small table, and a view of the city.

4. Furnished Apartments near Encore Boston

Everett

Gina

includes taxes & fees

9 Nov - 10 Nov

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

5. Maverick Suites at 28 Fenway

Fenway–Kenmore

Judy

includes taxes & fees

1 Dec - 2 Dec

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

6. Crescent Suites Hotel

South Side

Kasandra

includes taxes & fees

24 Nov - 25 Nov

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

7. The Chester Hotel

South End

Tracy

includes taxes & fees

9 Nov - 10 Nov

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

8. Kasa Boston at Fenway

Fenway–Kenmore

antonio

includes taxes & fees

23 Nov - 24 Nov

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

9. Maverick Suites at 40 Temple St

Beacon Hill

Andrea

includes taxes & fees

1 Dec - 2 Dec

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

10. Maverick Suites at 245 Newbury St

Back Bay

Chloe

includes taxes & fees

6 Dec - 7 Dec

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

11. Temple Place Suites

Downtown Boston

James

includes taxes & fees

1 Dec - 2 Dec

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

12. Premier Suites - Bay Village

Bay Village

Jaetaek

includes taxes & fees

23 Nov - 24 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.

13. The Monty Boston

Downtown Boston

Jodi

includes taxes & fees

9 Nov - 10 Nov

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

14. The Concord Hotel

South End

Rupintal

includes taxes & fees

11 Nov - 12 Nov

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

15. Maverick Suites at 89 Marion

Coolidge Corner

Edna

includes taxes & fees

1 Dec - 2 Dec

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

16. Charlesgate Suites

Fenway–Kenmore

Ana

includes taxes & fees

23 Nov - 24 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.

17. Maverick Suites at 400 Columbus Ave

South End

Lorne

includes taxes & fees

3 Dec - 4 Dec

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

18. 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

includes taxes & fees

9 Nov - 10 Nov

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

19. Furnished Apartment Near Longwood

North Brookline

ANITA

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a sofa, a dining table, and a kitchen area with appliances.

20. Luxury 2BR near Cambridge

Prospect Hill

Carrie-Anne

includes taxes & fees

9 Nov - 10 Nov

View all properties

Find holiday rentals that suit your style

Top Winthrop Hotel Reviews

A hotel room with a bed, a desk with a lamp, a TV, and a map on the wall.

Château sur Mer Bed & Breakfast

Winthrop

8/10 Good

Anonymous traveller

A modern lounge area with a central fire feature, seating arrangements, and decorative wall panels.

Holiday Inn Express Boston Logan Airport - Revere by IHG

Revere

10/10 Excellent

Stephen

An outdoor seating area with a fire pit, sofas, and chairs.

Hyatt Place Boston/Seaport District

Seaport District

10/10 Excellent

Clifford E

A modern living room with a fireplace, two armchairs, a coffee table, and a striped rug.

Hampton Inn Boston - Logan Airport

Revere

10/10 Excellent

Judith

A brick building with a large arched entrance, two flags, and a sign reading "THE DAGNY".

The Dagny Boston

Downtown Boston

10/10 Excellent

Stephen

A modern hotel with a prominent Hampton Inn sign, featuring a multi-story structure with a central courtyard and a landscaped area.

Hampton by Hilton at the Boston Seaport District

Seaport District

10/10 Excellent

Karen

A modern bridge with illuminated cables, a hotel with multiple floors, and a clear view of the surrounding urban area.

SpringHill Suites by Marriott Boston Logan Airport Revere Beach

Revere

10/10 Excellent

Thi mai Huong

An outdoor cafe with tables and chairs, a building entrance, and a street sign.

Harborside Inn Of Boston

Downtown Boston

10/10 Excellent

Brett

A lobby with curved seating, a central circular design on the floor, and a reception desk with a marble counter.

Renaissance® Boston Seaport District

Seaport District

10/10 Excellent

Robert

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, 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 favourite 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 depend 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 AU$297 per night. Entering your travel dates in the search wizard might find you 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.

Explore a world of travel with Expedia

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Winthrop Holiday Rentals

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. Furnished Apartments near Encore Boston

5. Maverick Suites at 28 Fenway

6. Crescent Suites Hotel

7. The Chester Hotel

8. Kasa Boston at Fenway

9. Maverick Suites at 40 Temple St

10. Maverick Suites at 245 Newbury St

11. Temple Place Suites

12. Premier Suites - Bay Village

13. The Monty Boston

14. The Concord Hotel

15. Maverick Suites at 89 Marion

16. Charlesgate Suites

17. Maverick Suites at 400 Columbus Ave

18. Furnished Apartment near BMC

19. Furnished Apartment Near Longwood

20. Luxury 2BR near Cambridge

Find holiday rentals that suit your style

Top Winthrop Hotel Reviews

Château sur Mer Bed & Breakfast

8/10 Good

Find out more about Winthrop

Winthrop holiday rentals: An excellent choice for every season

How to find incredible deals on Winthrop rentals

Frequently Asked Questions

Can I find a holiday rental in Winthrop?

What are some of the best holiday rentals that Winthrop has to offer?

How many holiday rentals are there in Winthrop?

What can I see and do in Winthrop?

What are holiday rentals like in Winthrop?

Explore a world of travel with Expedia