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
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.
The price is ￥37,649
￥67,986 total
includes taxes & fees
Oct 28 - Oct 29
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.
The price is ￥15,687
￥35,046 total
includes taxes & fees
Nov 2 - Nov 3
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
9.8 out of 10, Exceptional, (6 reviews)
The price is ￥29,637
￥60,967 total
includes taxes & fees
Nov 9 - Nov 10
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
The price is ￥47,061
￥68,162 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

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
The price is ￥38,935
￥44,755 total
includes taxes & fees
Nov 25 - Nov 26
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
The price is ￥16,833
￥37,886 total
includes taxes & fees
Nov 22 - Nov 23
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, (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 ￥15,756
￥48,223 total
includes taxes & fees
Nov 9 - Nov 10
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
The price is ￥18,072
￥40,608 total
includes taxes & fees
Nov 1 - Nov 2
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, (1,336 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is ￥20,281
￥22,654 total
includes taxes & fees
Nov 1 - Nov 2
Crescent Suites 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.

10. 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
The price is ￥23,860
￥59,244 total
includes taxes & fees
Nov 1 - Nov 2
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

11. 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
The price is ￥28,237
￥46,577 total
includes taxes & fees
Nov 9 - Nov 10
Kasa Boston at Fenway
A compact kitchen with white cabinets, a black countertop, and two wooden chairs.

12. 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.
The price is ￥39,218
￥77,361 total
includes taxes & fees
Nov 20 - Nov 21
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.

13. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (44 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 ￥144,836
￥193,538 total
includes taxes & fees
Nov 1 - Nov 2
The Monty Boston
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

14. 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
The price is ￥16,801
￥34,640 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 28 Fenway
A building with a sign reading "GREEN TURTLE" and a dock with red chairs.

15. 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, (267 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.
The price is ￥42,214
￥76,115 total
includes taxes & fees
Nov 8 - Nov 9
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.

16. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (37 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is ￥24,126
￥47,571 total
includes taxes & fees
Nov 22 - Nov 23
The Concord Hotel
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

17. 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
The price is ￥19,695
￥37,065 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 40 Temple St
A row of brick buildings with storefronts, including a bakery and a liquor store.

18. 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
The price is ￥20,330
￥37,795 total
includes taxes & fees
Nov 15 - Nov 16
Maverick Suites at 245 Newbury St
A deck with wicker furniture and a table, overlooking a marina with boats.

19. 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.

20. 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.
The price is ￥66,670
￥118,473 total
includes taxes & fees
Nov 10 - Nov 11
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.
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Top Winthrop Hotel Reviews

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop using one of the methods below:

  • View our selection of featured holiday rentals in Winthrop
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Look no further and take a look at our great range of rental properties in Winthrop!

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.