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

Winthrop Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winthrop holiday rentals

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

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Winthrop
9.2 out of 10, Wonderful, (21 reviews)
"Very amazing room to stay! Everything was very clean and comfortable! Host was very responsive and wonderful!"
United States
Edmund W.
The price is NZ$381
includes taxes & fees
10 Nov - 11 Nov
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

2. Steps from the ocean - minutes from Boston

Steps from the ocean - minutes from Boston
Winthrop
9.8 out of 10, Exceptional, (6 reviews)
The price is NZ$669
includes taxes & fees
19 Nov - 20 Nov
Steps from the ocean - minutes from Boston

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

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
The price is NZ$718
includes taxes & fees
8 Nov - 9 Nov
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, (51 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 NZ$506
includes taxes & fees
9 Nov - 10 Nov
Bright 2BR by Boston Waterfront

5. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (770 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is NZ$430
includes taxes & fees
29 Nov - 30 Nov
Global Luxury Suites Downtown Boston

6. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (37 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is NZ$552
includes taxes & fees
9 Nov - 10 Nov
The Concord Hotel

7. Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
8.6 out of 10, Excellent, (10 reviews)
"It was close to Boston and the airport"
United States
Lewis
The price is NZ$637
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

8. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (162 reviews)
"Great property in a great location. Tons of food options nearby. Walking distance to Target and Whole Foods. Easy access to the Blue line. The neighborhood was quiet and clean. Boston common is just a block away. Definitely would stay again and highly recommend."
United States
TommyWallace
The price is NZ$369
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 40 Temple St

9. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (345 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is NZ$527
includes taxes & fees
9 Nov - 10 Nov
Kasa Boston at Fenway

10. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (119 reviews)
"The houseboat was great! Everyone was super friendly and helpful. Can’t wait for our next stay!"
United States
Frank M.
The price is NZ$824
includes taxes & fees
30 Nov - 1 Dec
Fun houseboat. Walk to Boston attractions WIFI

11. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (216 reviews)
"It was a great location right in a little neighborhood with shops and restaurants. There are two subway stations within a 5 minute walk which made getting to the T very easy. The room was perfect for us!"
United States
David
The price is NZ$457
includes taxes & fees
22 Nov - 23 Nov
Maverick Suites at 245 Newbury St

12. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (680 reviews)
"I can’t believe this property is a hotel and not a historic landmark. If you like historical places this is the place to stay in Boston."
United States
Benny
The price is NZ$496
includes taxes & fees
30 Nov - 1 Dec
Marriott Vacation Club® at Custom House, Boston

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

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (213 reviews)
"Wonderful brief stay!"
United States
Marie T.
The price is NZ$884
includes taxes & fees
2 Dec - 3 Dec
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

14. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (42 reviews)
"Charming historic building with modern room interiors and amenities, high quality linens/towels, and an easy walk to BSO, Northeastern University, and shopping."
United States
Andrew
The price is NZ$519
includes taxes & fees
3 Nov - 4 Nov
The Chester Hotel

15. Boston Financial District 1BR | Walk to anything!

Boston Financial District 1BR | Walk to anything!
Downtown Boston
9.6 out of 10, Exceptional, (4 reviews)
"The place was as advertised: clean, within walking distance to a lot of places. Note that Its central location, while convenient, is also a drawback due to road noise. Make sure you pack a very good set of ear plugs, not the foam cheapo ones that airlines give you for free. You will need them to block out the traffic noise from below your bedroom window."
United States
Popsicle T.
The price is NZ$481
includes taxes & fees
1 Dec - 2 Dec
Boston Financial District 1BR | Walk to anything!

16. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
9.0 out of 10, Wonderful, (24 reviews)
"Great location."
United States
Chloe
The price is NZ$362
includes taxes & fees
4 Nov - 5 Nov
Stunning Back Bay Studio Apartment

17. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (471 reviews)
"Great location!"
United States
Mario Quezada
The price is NZ$383
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 28 Fenway

18. Modern Studio | South End

Modern Studio | South End
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"Amazing stay in the best location! Would recommend and stay here again!!"
United States
Kaylee P.
The price is NZ$347
includes taxes & fees
16 Nov - 17 Nov
Modern Studio | South End

19. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (186 reviews)
"Very well located. Close to two subways and Copeland Square."
Canada
Lorne
The price is NZ$395
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 400 Columbus Ave

20. Stellar South End Studio

Stellar South End Studio
Back Bay
9.4 out of 10, Exceptional, (6 reviews)
"The room was clean and quiet."
United States
Beth
The price is NZ$387
includes taxes & fees
16 Nov - 17 Nov
Stellar South End Studio
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winthrop Hotel Reviews

Find out more about Winthrop

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winthrop holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winthrop. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winthrop. Seeing all the best attractions is bound to make you fall in love with Winthrop. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winthrop short-term rentals, that won’t be hard to do.

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.