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

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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 £363
includes taxes & fees
30 Sept - 1 Oct
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking

2. 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, (15 reviews)
"Great location and wonderful hosts! Would definitely recommend to anyone staying in the Boston area. "
United States
Kristie P.
The price is £198
includes taxes & fees
27 Sept - 28 Sept
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

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

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
The price is £283
includes taxes & fees
30 Sept - 1 Oct
Beautiful 3-bedroom apartment with AC in welcoming Winthrop

4. 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, (667 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is £518
includes taxes & fees
8 Oct - 9 Oct
Marriott Vacation Club® at Custom House, Boston

5. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (748 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is £344
includes taxes & fees
30 Sept - 1 Oct
Global Luxury Suites Downtown Boston

6. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (148 reviews)
"There only a few things I require from a hotel. Hotel Maverick Suites at 40 are clean, quiet and reasonably priced. I enjoyed my stay there immensely. A bonus was their convenient location."
United States
Jerrold
The price is £204
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 40 Temple St

7. Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat

Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat
Boston
10.0 out of 10, Exceptional, (136 reviews)
"I reserved the Green Turtle for out-of-town guests over Memorial Day weekend and will do so again. They will thrilled to stay on the water their first time visiting Boston and found the boat comfortable and restful."
United States
Gale P.
The price is £439
includes taxes & fees
28 Sept - 29 Sept
Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat

8. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (44 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 £248
includes taxes & fees
28 Sept - 29 Sept
Bright 2BR by Boston Waterfront

9. The Heart of Southie (Garage + Roof Deck)

The Heart of Southie (Garage + Roof Deck)
South Boston
10.0 out of 10, Exceptional, (72 reviews)
"Great apartment-no issues. We enjoyed our stay."
United States
Kathryn M.
The price is £605
includes taxes & fees
24 Sept - 25 Sept
The Heart of Southie (Garage + Roof Deck)

10. Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
9.4 out of 10, Exceptional, (126 reviews)
"The dedicated parking spots was a huge plus."
United States
Ted W.
The price is £520
includes taxes & fees
4 Oct - 5 Oct
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

11. Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown

Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (88 reviews)
"Fun and unique experience staying on a boat! Great host!"
United States
Jeremy H.
The price is £415
includes taxes & fees
30 Sept - 1 Oct
Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown

12. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (24 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is £319
includes taxes & fees
21 Oct - 22 Oct
The Concord Hotel

13. Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC

Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (73 reviews)
"Great location and the host was very helpful for everything. Definitely I’m gonna stay here again."
United States
Sandy M.
The price is £345
includes taxes & fees
7 Oct - 8 Oct
Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC

14. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (327 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is £214
includes taxes & fees
24 Sept - 25 Sept
Near Boston Historic two-bedroom with Modern Amenities

15. 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, (203 reviews)
The price is £253
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 245 Newbury St

16. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,280 reviews)
"Great location, close to restaurants and stores. Beautiful rooms. Close enought to Boston without all the traffic. Close to Mass Pike."
United States
Mark
The price is £135
includes taxes & fees
27 Sept - 28 Sept
Crescent Suites Hotel

17. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (41 reviews)
"We loved the location and the host was amazing. We only wish the sidewalk construction wasn’t going on because it obstructed part of the beautiful view."
United States
Jodi
The price is £777
includes taxes & fees
4 Oct - 5 Oct
The Monty Boston

18. Right Near Convention Center and Train Station

Right Near Convention Center and Train Station
South Boston
10.0 out of 10, Exceptional, (43 reviews)
"It was amazing Peter was fantastic. We would definitely stay here again."
United States
Kathy M.
The price is £656
includes taxes & fees
8 Oct - 9 Oct
Right Near Convention Center and Train Station

19. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (315 reviews)
"Room was clean, neat area."
United States
Keir
The price is £164
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 89 Marion

20. Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.

Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
Charlestown
10.0 out of 10, Exceptional, (258 reviews)
"Loved this experience!!! Would book this again! So convenient to see Boston! "
United States
Ellen Z.
The price is £351
includes taxes & fees
7 Oct - 8 Oct
Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
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, 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 £135 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 Boston Harbor.

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.