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

Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winthrop vacation rentals

A hallway with a framed artwork of a person and a colorful bird illustration on the wall.

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, (22 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 SAR 372
SAR 788 total
includes taxes & fees
5 Nov - 6 Nov
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
A dining area with a round table set for four, a sofa in the background, and a decorative wall piece.

2. Steps from the ocean - minutes from Boston

Steps from the ocean - minutes from Boston
Winthrop
9.8 out of 10, Exceptional, (6 reviews)
Steps from the ocean - minutes from Boston
A modern kitchen with wooden cabinets, a refrigerator, and a dining area with chairs.

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

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

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 SAR 437
SAR 1,179 total
includes taxes & fees
9 Nov - 10 Nov
Bright 2BR by Boston Waterfront
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

5. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (772 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is SAR 405
SAR 909 total
includes taxes & fees
29 Nov - 30 Nov
Global Luxury Suites Downtown Boston
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

6. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (38 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is SAR 601
SAR 1,166 total
includes taxes & fees
8 Nov - 9 Nov
The Concord Hotel
A modern living room with a sofa, coffee table, and a small table with books and a lamp. There is a kitchen area with cabinets, a refrigerator, and a microwave. A welcome sign is on the wall, and a basketball arcade game is visible.

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
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

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, (164 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 SAR 378
SAR 780 total
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 40 Temple St
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

9. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (347 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is SAR 733
SAR 1,180 total
includes taxes & fees
2 Dec - 3 Dec
Kasa Boston at Fenway
A room with a large window overlooking a marina with boats and buildings.

10. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (120 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 SAR 499
SAR 1,799 total
includes taxes & fees
5 Nov - 6 Nov
Fun houseboat. Walk to Boston attractions WIFI
A row of brick buildings with storefronts, including a bakery and a liquor store.

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, (217 reviews)
"Great location - plenty to do."
United States
Chloe
The price is SAR 541
SAR 967 total
includes taxes & fees
22 Nov - 23 Nov
Maverick Suites at 245 Newbury St
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

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 SAR 858
SAR 987 total
includes taxes & fees
25 Nov - 26 Nov
Marriott Vacation Club® at Custom House, Boston
A marina with boats docked, a red brick building, and modern high-rise apartments in the background.

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 SAR 553
SAR 2,016 total
includes taxes & fees
8 Nov - 9 Nov
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

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 SAR 540
SAR 1,096 total
includes taxes & fees
10 Nov - 11 Nov
The Chester Hotel
A living room with a sofa, two chairs, a coffee table, and a TV.

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.
Boston Financial District 1BR | Walk to anything!
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

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

17. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (473 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is SAR 385
SAR 809 total
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 28 Fenway
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

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 SAR 267
SAR 726 total
includes taxes & fees
16 Nov - 17 Nov
Modern Studio | South End
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.

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 SAR 426
SAR 834 total
includes taxes & fees
11 Nov - 12 Nov
Maverick Suites at 400 Columbus Ave
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

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
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.
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Top Winthrop Hotel Reviews

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"The strike was the only negative aspect of an otherwise perfect stay."
Ira 3-night trip
Posted less than an hour ago
Encore Boston Harbor

Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals near top points of interest in Winthrop, or you can choose a more secluded option if you're looking for relaxation. Visitors to Winthrop speak positively about the beaches and restaurants in this destination. Make sure you have time to check out the cafes and waterfront during your trip.

What are some of the best vacation home rentals in Winthrop?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This vacation home rental near 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a hot tub and a selection of books.

How many vacation rentals are there in Winthrop?

With 6 Expedia vacation rentals, you're sure 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 vacation rentals like in Winthrop?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Winthrop. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.