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

Winthrop Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

Rooftop terrace

1. 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, (664 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is NT$14,781
NT$16,991 total
includes taxes & fees
Sep 13 - Sep 14
Marriott Vacation Club® at Custom House, Boston
Lobby lounge

2. 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 NT$8,552
NT$13,705 total
includes taxes & fees
Sep 11 - Sep 12
Global Luxury Suites Downtown Boston
Studio

3. 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 NT$6,627
NT$11,596 total
includes taxes & fees
Sep 11 - Sep 12
The Concord Hotel
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, (145 reviews)
"Worth the stay"
Canada
Akansha
The price is NT$4,276
NT$7,813 total
includes taxes & fees
Sep 13 - Sep 14
Maverick Suites at 40 Temple St
Exterior

5. 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 NT$6,797
NT$10,706 total
includes taxes & fees
Sep 11 - Sep 12
Maverick Suites at 245 Newbury St
Living area

6. 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 NT$5,097
NT$8,753 total
includes taxes & fees
Sep 11 - Sep 12
Maverick Suites at 400 Columbus Ave
Luxury Suite 3 | Living area

7. 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 NT$15,805
NT$23,602 total
includes taxes & fees
Sep 29 - Sep 30
The Monty Boston
Lobby

8. 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 NT$4,956
NT$8,952 total
includes taxes & fees
Sep 20 - Sep 21
Kasa Boston at Fenway
Premium Apartment | Living area

9. 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 NT$5,381
NT$10,164 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)

10. 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 NT$3,795
NT$6,351 total
includes taxes & fees
Sep 13 - Sep 14
Temple Place Suites
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, (419 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is NT$6,262
NT$10,272 total
includes taxes & fees
Sep 13 - Sep 14
Maverick Suites at 28 Fenway
Premium Studio Suite

12. 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 NT$6,451
NT$12,841 total
includes taxes & fees
Sep 13 - Sep 14
Charlesgate Suites
Deluxe Double Room, Shared Bathroom

13. 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 NT$3,795
NT$5,990 total
includes taxes & fees
Sep 13 - Sep 14
Premier Suites - Bay Village
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

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Recommend"
Hoai 2-night trip
Posted 6 hours ago
Seaport Hotel Boston

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
  • Use the map to find apartments and other holiday homes in the Winthrop neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winthrop while they last

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 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.

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.