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

Winthrop Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winthrop vacation rentals

A two-story brick house with a front porch, a staircase, and a well-maintained lawn.

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 AED 338
AED 747 total
includes taxes & fees
7 Dec - 8 Dec
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
A coastal landscape with a beach, a lighthouse, and industrial structures in the background.

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 AED 509
AED 1,197 total
includes taxes & fees
13 Dec - 14 Dec
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
10.0 out of 10, Exceptional, (1 review)
"We used this apartment as home base for our weekend in Salem and Boston. An easy drive to both, the apartment was easy to get to, and check-in was a breeze. This is not 5-star accommodations, but it was very comfortable and was perfect for our weekend adventures. The host was responsive to my questions and the whole thing went smoothly. We’d recommend the apartment to others looking for an easy, safe place to stay for a trip to the Boston area."
United States
Kristen S.
The price is AED 1,102
AED 1,514 total
includes taxes & fees
14 Nov - 15 Nov
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
A multi-story hotel with a classic architectural style, featuring arched windows and a central entrance.

4. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (776 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is AED 356
AED 843 total
includes taxes & fees
14 Dec - 15 Dec
Global Luxury Suites Downtown Boston
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

5. 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, (169 reviews)
"great location near the commons. nice space for single traveler."
United States
Andrea
The price is AED 260
AED 636 total
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 40 Temple St
A row of brick buildings with storefronts, including a bakery and a liquor store.

6. 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, (219 reviews)
"Great location - plenty to do."
United States
Chloe
The price is AED 275
AED 654 total
includes taxes & fees
13 Dec - 14 Dec
Maverick Suites at 245 Newbury St
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a toaster.

7. 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 AED 357
AED 1,056 total
includes taxes & fees
15 Nov - 16 Nov
Bright 2BR by Boston Waterfront
A room with a bed, a round table, chairs, a large mirror, and a view of greenery outside.

8. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.2 out of 10, Very good, (41 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is AED 542
AED 1,088 total
includes taxes & fees
13 Dec - 14 Dec
The Concord Hotel
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

9. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (477 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is AED 377
AED 792 total
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 28 Fenway
A wooden hallway with a patterned floor leading to a door.

10. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (357 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is AED 291
AED 653 total
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 89 Marion
A brick building with a green awning labeled "The UPS Store" and a door marked "402".

11. 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 AED 291
AED 672 total
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 400 Columbus Ave
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, (682 reviews)
"Nice hotel with a great location. Rooms were very spacious with many amenities to offer. Will definitely be back again."
United States
Joseph
The price is AED 952
AED 1,095 total
includes taxes & fees
29 Nov - 30 Nov
Marriott Vacation Club® at Custom House, Boston
A neatly made bed with a white comforter and a beige throw blanket, a brown leather chair, a small bedside table with a lamp, and a framed picture on the wall.

13. Pet Friendly - Laundry in Bldg - FIDI

Pet Friendly - Laundry in Bldg - FIDI
Downtown Boston
10.0 out of 10, Exceptional, (2 reviews)
"This property is in a fantastic location! My husband"
United States
Kathryn
The price is AED 279
AED 852 total
includes taxes & fees
7 Dec - 8 Dec
Pet Friendly - Laundry in Bldg - FIDI
A waterfront building with a round tower, a dock with boats, and a calm water body reflecting the structure.

14. 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 AED 471
AED 1,749 total
includes taxes & fees
7 Dec - 8 Dec
Fun houseboat. Walk to Boston attractions WIFI
A modern living room with large windows, a sofa, a coffee table, and a lamp.

15. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (352 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is AED 661
AED 1,091 total
includes taxes & fees
23 Nov - 24 Nov
Kasa Boston at Fenway
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, (25 reviews)
"Great location."
United States
Chloe
The price is AED 234
AED 725 total
includes taxes & fees
8 Dec - 9 Dec
Stunning Back Bay Studio Apartment
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

17. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (45 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
The price is AED 516
AED 1,057 total
includes taxes & fees
22 Nov - 23 Nov
The Chester Hotel
A waterfront building with a round tower, a dock with boats, and a calm water body reflecting the structure.

18. 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 AED 477
AED 1,900 total
includes taxes & fees
14 Dec - 15 Dec
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A bedroom with a wooden nightstand, a white bed, and a white wall.

19. Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.8 out of 10, Good, (21 reviews)
"Good location and space for the price relative to other options. Functional, but dated property that is clean and meet up with host representative for key hand off was accommodating of a late arrival."
United States
Gary
The price is AED 371
AED 943 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Studio Steps from Boston Common and Theaters
A modern living room with a sofa, a teal chair, and a coffee table. There is a kitchen area with wooden cabinets and a refrigerator.

20. Warr15-1/1 · Comfy 1br, Minutes to Boston Common, 99 Walk score

Warr15-1/1 · Comfy 1br, Minutes to Boston Common, 99 Walk score
Bay Village
9.2 out of 10, Wonderful, (5 reviews)
"The space was immaculately clean and adequately furnished. The location was great, right off of the Tufts Medical Center Subway stop. The host was friendly, communicative, and quick to reply back. The bed was a bit creaky, and the wall ac units were loud for myself but not for my friend (who is accustomed to sleeping with white noise), just fyi. Otherwise, an excellent choice of stay!"
United States
Nina C.
The price is AED 262
AED 853 total
includes taxes & fees
6 Dec - 7 Dec
Warr15-1/1 · Comfy 1br, Minutes to Boston Common, 99 Walk score
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Hotel Reviews

The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Great place to stay! Great location."
ROBERTA 3-night trip
Posted 1 hour ago
The Godfrey Hotel Boston

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.