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

Winthrop Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
9.0 out of 10, Wonderful, (18 reviews)
"This is a convenient small apartment. However, it should be made clear that it is under the flight path to Logan airport. There were planes flying over till around 23:30, and they started again around 05:30. They were pretty loud."
United Kingdom
Philip
$198 nightly
The price is $221
Nov 2 - Nov 3
Total with taxes and fees
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
A living room with a fireplace, a television, and a dining area with chairs and a table.

2. 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, (59 reviews)
"Absolutely awesome place to stay. We loved itFrankie was the best host. Parking was great. We would definitely stay there again"
United States
ronda t.
$371 nightly
The price is $414
Oct 26 - Oct 27
Total with taxes and fees
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
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
$389 nightly
The price is $435
Oct 20 - Oct 21
Total with taxes and fees
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
A waterfront cityscape with modern skyscrapers and a calm river.

4. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (49 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
$299 nightly
The price is $344
Nov 15 - Nov 16
Total with taxes and fees
Bright 2BR by Boston Waterfront
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

5. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (331 reviews)
"Absolutely gorgeous apartments! Concierge was very friendly!"
United States
Kelly
$270 nightly
The price is $297
Nov 9 - Nov 10
Total with taxes and fees
Kasa Boston at Fenway
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

6. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (763 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
$250 nightly
The price is $287
Nov 10 - Nov 11
Total with taxes and fees
Global Luxury Suites Downtown Boston
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

7. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (34 reviews)
"Great location, great Apartment"
United States
Carla Patricia
$276 nightly
The price is $317
Nov 2 - Nov 3
Total with taxes and fees
The Concord Hotel
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, (157 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
$252 nightly
The price is $290
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 40 Temple St
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

9. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (40 reviews)
"Location was very loud but thank God for earplugs. It was very clean but very old. Very expensive for such a location and room. I always believe in paying for what u get but I paid a lot for 3 nights."
United States
Luda
$249 nightly
The price is $287
Nov 1 - Nov 2
Total with taxes and fees
The Chester Hotel
A row of brick buildings with storefronts, including a bakery and a liquor store.

10. 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, (207 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
$240 nightly
The price is $276
Nov 15 - Nov 16
Total with taxes and fees
Maverick Suites at 245 Newbury St
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

11. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (446 reviews)
"Great price for the place given the location."
United States
Beenish
$234 nightly
The price is $269
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 28 Fenway
A marina with boats docked, a red brick building, and modern high-rise apartments in the background.

12. 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, (211 reviews)
"Such a quaint and quiet location. We loved staying on the pier. The boat was clean and tidy!! We would definitely stay there again!!"
United States
Angela L.
$442 nightly
The price is $508
Nov 9 - Nov 10
Total with taxes and fees
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A room with a large window overlooking a marina with boats and buildings.

13. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (116 reviews)
"Rustic boathouse in a great central location ."
United States
William M.
$411 nightly
The price is $473
Nov 9 - Nov 10
Total with taxes and fees
Fun houseboat. Walk to Boston attractions WIFI
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.

14. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (181 reviews)
"Well located"
United States
Evelyn
$206 nightly
The price is $237
Nov 9 - Nov 10
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
A wooden hallway with a patterned floor leading to a door.

15. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (338 reviews)
"The area was walkable and the room was great!"
United States
Edna
$206 nightly
The price is $230
Nov 15 - Nov 16
Total with taxes and fees
Maverick Suites at 89 Marion
A compact kitchen with white cabinets, a black countertop, and two wooden chairs.

16. Modern 2 BR, 1BA Near Menino Convention Center & Seaport District

Modern 2 BR, 1BA Near Menino Convention Center & Seaport District
South Boston
9.8 out of 10, Exceptional, (244 reviews)
"Great location!!"
United States
Kellie S.
$370 nightly
The price is $425
Oct 18 - Oct 19
Total with taxes and fees
Modern 2 BR, 1BA Near Menino Convention Center & Seaport District
A waterfront building with a sign reading "Turtle," featuring a dock with red chairs and potted plants.

17. 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, (76 reviews)
"Great location and the host was very helpful for everything. Definitely I’m gonna stay here again."
United States
Sandy M.
$420 nightly
The price is $483
Oct 28 - Oct 29
Total with taxes and fees
Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
A waterfront cityscape with a prominent clock tower, a river with boats, and modern buildings.

18. Location+Comfort+Convenience

Location+Comfort+Convenience
East Boston
9.4 out of 10, Exceptional, (89 reviews)
"Fantastic location, easy access to Maverick station! Cozy space. Convenient to restaurants and the mattresses are excellent!"
United States
Elaine S.
$313 nightly
The price is $360
Oct 21 - Oct 22
Total with taxes and fees
Location+Comfort+Convenience
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

19. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,316 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
$139 nightly
The price is $155
Nov 5 - Nov 6
Total with taxes and fees
Crescent Suites Hotel
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

20. 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, (676 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
$372 nightly
The price is $428
Nov 13 - Nov 14
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Clean quite room in a great location."
Kevin 3-night trip
Posted less than an hour ago
Harborside Inn Of Boston

Find out more about Winthrop

Everything you need to know about Winthrop vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winthrop in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $155 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop vacation 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 vacation.

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 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.