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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winthrop vacation rentals

Interior

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, (57 reviews)
"Had a great stay here! Had a little issue at check in, and Frankie immediately responded to my phone call. Considering the quick response and resolution, I wouldn't hesitate to stay at any of his properties again! Nice location and definitely take him up on his restaurant recommendations... we tried out Jac's for breakfast and it was phenomenal and by far the least expensive meal on our entire trip. The house is a bit ran down in areas and doesn't feel super secure, but it is overall a very cool...
United States
Stacy B.
The price is ￥29,253
￥56,309 total
includes taxes & fees
Sep 11 - Sep 12
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
Interior

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, (13 reviews)
"Great location and wonderful hosts! Would definitely recommend to anyone staying in the Boston area. "
United States
Kristie P.
The price is ￥153
￥16,440 total
includes taxes & fees
Sep 13 - Sep 14
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Living area

3. Steps from the ocean - minutes from Boston

Steps from the ocean - minutes from Boston
Winthrop
10.0 out of 10, Exceptional, (1 review)
"I traveled to Boston for my nieces wedding and had her 3 daughters ages 13,7, and 5 staying with me. This place was perfect!! We had plenty of space and the very short walk to the beach was great! The girls loved the beach which was very clean and not too crowded. We enjoyed our stay very much."
United States
Wenona S.
The price is ￥30,722
￥61,719 total
includes taxes & fees
Sep 13 - Sep 14
Steps from the ocean - minutes from Boston
Interior

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

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
The price is ￥38,330
￥56,687 total
includes taxes & fees
Sep 16 - Sep 17
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Rooftop terrace

5. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (665 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is ￥71,907
￥82,657 total
includes taxes & fees
Sep 13 - Sep 14
Marriott Vacation Club® at Custom House, Boston
Lobby lounge

6. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (741 reviews)
"Great for the price; central to everything"
United States
afshin
The price is ￥41,673
￥66,779 total
includes taxes & fees
Sep 11 - Sep 12
Global Luxury Suites Downtown Boston
Studio

7. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very Good, (21 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is ￥33,942
￥58,402 total
includes taxes & fees
Sep 12 - Sep 13
The Concord Hotel
Front of property

8. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (145 reviews)
"Worth the stay"
Canada
Akansha
The price is ￥20,802
￥38,010 total
includes taxes & fees
Sep 13 - Sep 14
Maverick Suites at 40 Temple St
Exterior

9. 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, (202 reviews)
"Great location, really cool place!"
United States
lane
The price is ￥33,117
￥52,167 total
includes taxes & fees
Sep 11 - Sep 12
Maverick Suites at 245 Newbury St
Living area

10. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (171 reviews)
"Well located"
United States
Evelyn
The price is ￥24,838
￥42,651 total
includes taxes & fees
Sep 11 - Sep 12
Maverick Suites at 400 Columbus Ave
Luxury Suite 3 | Living area

11. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (40 reviews)
"This place is absolutely stunning I would definitely book again. "
United States
Klaudia
The price is ￥76,890
￥114,822 total
includes taxes & fees
Sep 29 - Sep 30
The Monty Boston
Lobby

12. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (314 reviews)
"Everything is good"
United States
Kilyen
The price is ￥24,148
￥43,620 total
includes taxes & fees
Sep 13 - Sep 14
Kasa Boston at Fenway
Premium Apartment | Living area

13. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is ￥26,218
￥49,525 total
includes taxes & fees
Sep 11 - Sep 12
The Chester Hotel
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up)

14. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (465 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is ￥18,491
￥30,950 total
includes taxes & fees
Sep 13 - Sep 14
Temple Place Suites
Front of property

15. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (419 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is ￥30,511
￥50,052 total
includes taxes & fees
Sep 13 - Sep 14
Maverick Suites at 28 Fenway
Premium Studio Suite

16. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (233 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is ￥31,431
￥62,569 total
includes taxes & fees
Sep 13 - Sep 14
Charlesgate Suites
Deluxe Double Room, Shared Bathroom

17. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (339 reviews)
"Location is great"
United States
Eria
The price is ￥18,491
￥29,186 total
includes taxes & fees
Sep 13 - Sep 14
Premier Suites - Bay Village
Room

18. North End Studio

North End Studio
North End
9.4 out of 10, Exceptional, (70 reviews)
"Just like the picture showed, very clean and up to date look. Loved the mini apartment, perfect for us. In a very busy area, the North End. We loved it, so many spots to eat and centrally located. Felt very safe. Our host got back to us quickly when needed. Easy instructions when we arrived. I would highly recommend"
United States
Francine
The price is ￥36,797
￥71,204 total
includes taxes & fees
Sep 21 - Sep 22
North End Studio
Private kitchen

19. Lux 1st floor 3brm/1bath North End

Lux 1st floor 3brm/1bath North End
North End
10.0 out of 10, Exceptional, (11 reviews)
"The North End is a great neighborhood to stay in Boston. Convenient, fun and a food Mecca. The place was great - easy to find, clean, comfortable and a great location. I would wholeheartedly recommend it."
United States
Jack O.
The price is ￥75,893
￥136,764 total
includes taxes & fees
Sep 17 - Sep 18
Lux 1st floor 3brm/1bath North End
Interior

20. Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (18 reviews)
"Great location- excellent place!"
United States
Deborah S.
The price is ￥32,281
￥67,149 total
includes taxes & fees
Sep 14 - Sep 15
Perfetto North End 1brm
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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"No"
Meaghan 1-night trip
Posted less than an hour ago
Hyatt Regency Boston/Cambridge

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:

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Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals where you'll be only 3.7 mi (6 km) from New England Aquarium, giving you a more secluded option to escape the hustle and bustle. 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?

Cozy Salem Getaway. Historic Home Near All the Sights: This vacation home near Winthrop offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Massachusetts Bay 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 Boston Harbor.

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.