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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winthrop vacation rentals

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, WiFi (free), bed sheets

1. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (472 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is AED 400
AED 692 total
includes taxes & fees
20 Sep - 21 Sep
Temple Place Suites
Rooftop terrace

2. 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, (666 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is AED 1,764
AED 2,028 total
includes taxes & fees
18 Oct - 19 Oct
Marriott Vacation Club® at Custom House, Boston
42-inch TV with satellite channels

3. 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 AED 536
AED 953 total
includes taxes & fees
20 Sep - 21 Sep
Maverick Suites at 400 Columbus Ave
Front of property

4. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (146 reviews)
"Worth the stay"
Canada
Akansha
The price is AED 568
AED 990 total
includes taxes & fees
20 Sep - 21 Sep
Maverick Suites at 40 Temple St
Lobby

5. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (317 reviews)
"Excellent property upscale amenities full kitchen perfect in every way and my room was only a studio I’ll definitely be back next time to try a larger room just to see what they’re like"
United States
Dirk
The price is AED 511
AED 587 total
includes taxes & fees
20 Sep - 21 Sep
Kasa Boston at Fenway
Premium Apartment | Living area | 24-inch Smart TV with digital channels

6. 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 AED 735
AED 1,309 total
includes taxes & fees
18 Sep - 19 Sep
The Chester Hotel
Deluxe Double Room, Shared Bathroom | Iron/ironing board, WiFi (free), bed sheets

7. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (343 reviews)
"Location is great"
United States
Eria
The price is AED 423
AED 676 total
includes taxes & fees
20 Sep - 21 Sep
Premier Suites - Bay Village
Indoor pool, pool umbrellas, sun loungers

8. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (210 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is AED 959
AED 1,524 total
includes taxes & fees
20 Sep - 21 Sep
Global Luxury Suites East Boston
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, (203 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is AED 793
AED 1,250 total
includes taxes & fees
19 Sep - 20 Sep
Maverick Suites at 245 Newbury St
Lobby lounge

10. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (743 reviews)
"Friendly sat at Front and the property is very nice it was useful for a quick work trip. Easy to get around well lit and maintained"
United States
Christopher
The price is AED 1,169
AED 1,801 total
includes taxes & fees
30 Sep - 1 Oct
Global Luxury Suites Downtown Boston
Front of property

11. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (423 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is AED 658
AED 1,115 total
includes taxes & fees
20 Sep - 21 Sep
Maverick Suites at 28 Fenway
Studio | Iron/ironing board, WiFi (free)

12. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (23 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 AED 721
AED 1,294 total
includes taxes & fees
20 Sep - 21 Sep
The Concord Hotel
Apartment (1 Bedroom) | Interior

13. Apt in Historic Lynn Neighborhood: 5 Mi to Salem!

Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
3.0 star property
Lynn
Apt in Historic Lynn Neighborhood: 5 Mi to Salem!
Luxury Suite 3 | Living area | Smart TV, Netflix, Hulu, streaming services

14. 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 AED 2,735
AED 3,778 total
includes taxes & fees
4 Oct - 5 Oct
The Monty Boston
Premium Studio Suite | Premium bedding, desk, iron/ironing board, WiFi (free)

15. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (236 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is AED 735
AED 1,478 total
includes taxes & fees
21 Sep - 22 Sep
Charlesgate Suites
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down comforters

16. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (22 reviews)
"Great location, close to the T line, grocery store nearby. Clean, quiet and very comfortable accommodations, especially the best bed I’ve slept in at a rental location. Had everything we needed, looking forward to coming back!"
United States
Lori
The price is AED 1,633
AED 2,278 total
includes taxes & fees
20 Sep - 21 Sep
Symple Live
30-inch flat-screen TV with satellite channels, TV

17. Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
8.0 out of 10, Very good, (87 reviews)
"It was very close to stores to go shopping and amazing spot to get last minute reservations for dinner"
United States
Talyciah
The price is AED 521
AED 936 total
includes taxes & fees
28 Sep - 29 Sep
Maverick Suites at 402 Columbus Ave
Interior entrance

18. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (312 reviews)
"Stayed in the economy suite, very suitable for a couple! Very clean room and I have never had an easier check-in process!!"
United States
Paula
The price is AED 454
AED 835 total
includes taxes & fees
20 Sep - 21 Sep
Maverick Suites at 89 Marion
Apartment | Interior

19. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
7.6 out of 10, Good, (7 reviews)
"Easy to check in, students friendly apartment, convenient location, easy to call Uber or Lyft, and within 20 min. drive to the famous universities."
United States
Sujiang
Furnished Apartment Near Longwood
Terrace/patio

20. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,273 reviews)
"Great location, close to restaurants and stores. Beautiful rooms. Close enought to Boston without all the traffic. Close to Mass Pike."
United States
Mark
The price is AED 568
AED 635 total
includes taxes & fees
27 Sep - 28 Sep
Crescent Suites Hotel
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

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"The people upstairs were making so much noise and the staff and front desk handled things very quickly"
Jeffrey 1-night trip
Posted less than an hour ago
The Midtown Hotel MOD Collection by Sonesta

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.