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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winthrop vacation rentals

A living room with a fireplace, a television, and a dining area with chairs and a table.

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, (60 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.
$388 nightly
The price is $433
Oct 28 - Oct 29
Total with taxes and fees
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
A paved pathway leading to a waterfront, with trees and a building on one side.

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, (21 reviews)
"Very amazing room to stay! Everything was very clean and comfortable! Host was very responsive and wonderful!"
United States
Edmund W.
$200 nightly
The price is $223
Nov 2 - Nov 3
Total with taxes and fees
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.

3. Steps from the ocean - minutes from Boston

Steps from the ocean - minutes from Boston
Winthrop
9.6 out of 10, Exceptional, (5 reviews)
$348 nightly
The price is $389
Nov 9 - Nov 10
Total with taxes and fees
Steps from the ocean - minutes from Boston
A modern kitchen with wooden cabinets, a refrigerator, and a dining area with chairs.

4. 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 27 - Oct 28
Total with taxes and fees
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
A grand hall with a central circular platform, flanked by columns and flags.

5. 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, (678 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
$248 nightly
The price is $285
Nov 25 - Nov 26
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston
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, (769 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
$209 nightly
The price is $240
Nov 22 - Nov 23
Total with taxes and fees
Global Luxury Suites Downtown Boston
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.

7. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (50 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
$285 nightly
The price is $327
Nov 9 - Nov 10
Total with taxes and fees
Bright 2BR by Boston Waterfront
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

8. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (42 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
$246 nightly
The price is $283
Nov 1 - Nov 2
Total with taxes and fees
The Chester Hotel
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

9. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,334 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
$135 nightly
The price is $151
Nov 4 - Nov 5
Total with taxes and fees
Crescent Suites Hotel
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

10. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (338 reviews)
"Clean hotel. The space was very nice and open, Very accessible to everything I needed"
United States
Krista
$270 nightly
The price is $297
Nov 9 - Nov 10
Total with taxes and fees
Kasa Boston at Fenway
A compact kitchen with white cabinets, a black countertop, and two wooden chairs.

11. 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, (247 reviews)
"Great location!!"
United States
Kellie S.
$429 nightly
The price is $493
Nov 20 - Nov 21
Total with taxes and fees
Modern 2 BR, 1BA Near Menino Convention Center & Seaport District
A modern kitchen with a central island, a dining area with a round table and chairs, and a large window providing a view of the city at night.

12. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (43 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
$1,066 nightly
The price is $1,225
Nov 24 - Nov 25
Total with taxes and fees
The Monty Boston
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

13. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (460 reviews)
"Great price for the place given the location."
United States
Beenish
$212 nightly
The price is $244
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 28 Fenway
A building with a sign reading "GREEN TURTLE" and a dock with red chairs.

14. 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, (265 reviews)
"We had a wonderful time on the houseboat. We didn’t realize we would be sharing it with another couple (it has two rooms) and didn’t enjoy the same bed and breakfast amenities as we have at other B&Bs, but it was a unique experience and we woke up to some amazing sunrises. We did have a couple of minor issues that our hosts resolved quickly and they were very knowledgeable about the area - great restaurant recommendations! The location was perfect, close to the North End, Newberry St., and a...
United States
Shanan W.
$390 nightly
The price is $449
Nov 1 - Nov 2
Total with taxes and fees
Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

15. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (36 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
$265 nightly
The price is $304
Nov 22 - Nov 23
Total with taxes and fees
The Concord Hotel
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

16. 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, (159 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
$235 nightly
The price is $270
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 40 Temple St
A row of brick buildings with storefronts, including a bakery and a liquor store.

17. 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, (211 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 deck with wicker furniture and a table, overlooking a marina with boats.

18. 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
10.0 out of 10, Exceptional, (91 reviews)
"The host was super helpful and our family enjoyed the unique location."
United States
Katie P.
Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown
A deck with a sofa, chairs, and a table. An American flag is visible.

19. 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, (140 reviews)
"We loved sitting on the deck and feeling the sea breeze every morning and every night"
United States
Kat I.
$609 nightly
The price is $699
Nov 2 - Nov 3
Total with taxes and fees
Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat
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

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

8/10 Good
"I"
Patricia 3-night trip
Posted 2 hours ago
Four Points by Sheraton Boston Newton

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 $151 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.