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 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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, (657 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is P16,229
P18,655 total
includes taxes & fees
Aug 30 - Aug 31
Marriott Vacation Club® at Custom House, Boston
Front of property

2. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (142 reviews)
"Worth the stay"
Canada
Akansha
The price is P8,675
P15,654 total
includes taxes & fees
Aug 23 - Aug 24
Maverick Suites at 40 Temple St
Iron/ironing board, WiFi (free)

3. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (15 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 P9,899
P19,191 total
includes taxes & fees
Aug 20 - Aug 21
The Concord Hotel
Lobby lounge

4. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (735 reviews)
"Great for the price; central to everything"
United States
afshin
The price is P11,311
P20,444 total
includes taxes & fees
Aug 25 - Aug 26
Global Luxury Suites Downtown Boston
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, (200 reviews)
"Great location, really cool place!"
United States
lane
The price is P10,177
P17,380 total
includes taxes & fees
Aug 23 - Aug 24
Maverick Suites at 245 Newbury St
Lobby

6. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (306 reviews)
"The place was exactly as described, very comfortable and we had everything we needed for a relaxing stay. We especially appreciated the stocked kitchen essential pantry items!"
United States
KATERINA
The price is P19,464
P28,766 total
includes taxes & fees
Aug 21 - Aug 22
Kasa Boston at Fenway
Desk, iron/ironing board, WiFi (free), bed sheets

7. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (446 reviews)
"Great location so close to everything"
United States
Hunter
The price is P7,414
P12,410 total
includes taxes & fees
Aug 30 - Aug 31
Temple Place Suites
Living area

8. 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 P36,456
P52,560 total
includes taxes & fees
Aug 20 - Aug 21
The Monty Boston
Front of property

9. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (406 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
The price is P9,330
P16,762 total
includes taxes & fees
Aug 20 - Aug 21
Maverick Suites at 28 Fenway
42-inch TV with satellite channels

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, (165 reviews)
"Well located"
United States
Evelyn
The price is P9,074
P16,085 total
includes taxes & fees
Aug 31 - Sep 1
Maverick Suites at 400 Columbus Ave
Living area

11. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (37 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is P11,555
P21,095 total
includes taxes & fees
Aug 20 - Aug 21
The Chester Hotel
Iron/ironing board, WiFi (free), bed sheets

12. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (329 reviews)
"Lovely apartment and great stay. Location is very good with lots to do around"
United States
Obianuju
The price is P7,414
P11,720 total
includes taxes & fees
Aug 26 - Aug 27
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

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

8/10 Good
"Good hotel for a short stay-clean rooms, but they do charge an additional $200 deposit per room that I wasn’t expecting. Also, the parking garage only fits up to 6ft tall vehicles. Both of these should in a prominent place on websites before customers book. Or for the parking they should have a defined back up garage somewhere. Other than that-the rooms were good and modern looking."
Angela 2-night trip
Posted 2 hours ago
The Midtown Hotel MOD Collection by Sonesta

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 Donovan Beach are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include TD Garden and Fenway Park.

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.