A coastal town with a lighthouse, sandy beach, and residential buildings.

Winthrop Holiday Rentals

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Our top choices for Winthrop holiday rentals

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

Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
Winthrop
10.0 out of 10, Exceptional, (57 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
The price is AU$522
includes taxes & fees
1 Sept - 2 Sept
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking

2. Spectacular Oceanfront 1 Bedroom Unit in Winthrop

Spectacular Oceanfront 1 Bedroom Unit in Winthrop
Winthrop
9.8 out of 10, Exceptional, (26 reviews)
"This beach front stay made our girl's city trip so much more special.Excellent communication, very clean, and it had everything we needed and more. "
United States
Katie S.
The price is AU$743
includes taxes & fees
10 Aug - 11 Aug
Spectacular Oceanfront 1 Bedroom Unit in Winthrop

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

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
The price is AU$537
includes taxes & fees
23 Aug - 24 Aug
Beautiful 3-bedroom apartment with AC in welcoming Winthrop

4. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (40 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
The price is AU$437
includes taxes & fees
10 Aug - 11 Aug
Bright 2BR by Boston Waterfront

5. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.8 out of 10, Good, (141 reviews)
"Worth the stay"
Canada
Akansha
The price is AU$354
includes taxes & fees
11 Aug - 12 Aug
Maverick Suites at 40 Temple St

6. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (651 reviews)
"Best hotel for stay in Boston!"
United States
Frank
The price is AU$496
includes taxes & fees
30 Aug - 31 Aug
Marriott Vacation Club® at Custom House, Boston

7. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (36 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is AU$402
includes taxes & fees
9 Aug - 10 Aug
The Chester Hotel

8. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (433 reviews)
"Great location so close to everything"
United States
Hunter
The price is AU$286
includes taxes & fees
9 Aug - 10 Aug
Temple Place Suites

9. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (197 reviews)
"Location was perfect! The room was great and exactly what I needed for my business trip"
United States
Michael
The price is AU$373
includes taxes & fees
9 Aug - 10 Aug
Maverick Suites at 245 Newbury St

10. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.0 out of 10, Good, (10 reviews)
"Clean room and linens, great location and comfortable bed. Only complaint is the street noise and sounds from residents in upstairs apartment which was kind of loud. All things considered I’d stay again as it was a good value spot"
United States
Nancy
The price is AU$406
includes taxes & fees
9 Aug - 10 Aug
The Concord Hotel

11. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (733 reviews)
"Great property. Conveniently close to transit, shopping and Boston’s best districts."
United States
Neill
The price is AU$477
includes taxes & fees
25 Aug - 26 Aug
Global Luxury Suites Downtown Boston

12. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (161 reviews)
"Well located"
United States
Evelyn
The price is AU$333
includes taxes & fees
11 Aug - 12 Aug
Maverick Suites at 400 Columbus Ave

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

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
9.0 out of 10, Wonderful, (2 reviews)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
The price is AU$510
includes taxes & fees
20 Aug - 21 Aug
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

14. Primo North End Studio

Primo North End Studio
North End
9.4 out of 10, Exceptional, (19 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is AU$499
includes taxes & fees
16 Aug - 17 Aug
Primo North End Studio

15. Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (27 reviews)
"Excellent location, wonderful unit! "
United States
Mary M.
The price is AU$646
includes taxes & fees
14 Aug - 15 Aug
Prime Central 1brm in North End Boston

16. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (319 reviews)
"Lovely small property with thoughtful touches like cool water bottles & Nespresso available 24hrs. I had to take a last minute Zoom call and the front desk reserved the business center room for me. The rooms themselves are a bit small but very comfortable beds and linens."
United States
Theresa
The price is AU$233
includes taxes & fees
13 Aug - 14 Aug
Premier Suites - Bay Village

17. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.6 out of 10, Exceptional, (9 reviews)
"Perfect location! On a quiet street right in the heart of the Back Bay. Can easily walk to restaurants, grocery stores, the Prudential Center, and pubic transportation. Close to the nearby colleges which was helpful for our stay. We were able to support our college-age kid through a tough moment. It was clean, comfortable, and management was responsive and friendly. It was easy in and out. We’ll definitely come back. This would be perfect if you had any kind of medical emergency or needed to...
United States
Gretchen J.
The price is AU$357
includes taxes & fees
10 Aug - 11 Aug
Light-filled Studio | Back Bay

18. Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.6 out of 10, Good, (15 reviews)
"All good, would definitely stay again"
United States
Dan C.
The price is AU$382
includes taxes & fees
11 Aug - 12 Aug
Cozy Studio Steps from Boston Common and Theaters

19. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (202 reviews)
"Perfect location, professional staff, great parking arrangement "
United States
Joli
The price is AU$476
includes taxes & fees
12 Aug - 13 Aug
Global Luxury Suites East Boston

20. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (402 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
The price is AU$392
includes taxes & fees
10 Aug - 11 Aug
Maverick Suites at 28 Fenway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winthrop Hotel Reviews

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$233 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. 

Explore a world of travel with Expedia

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?

Steps from the ocean minutes from Boston Beach house for rent 10% off first week: This highly rated holiday home rental in Winthrop is located near the beach, and offers a selection of books, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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 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.