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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winthrop vacation rentals

A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

1. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (152 reviews)
"There only a few things I require from a hotel. Hotel Maverick Suites at 40 are clean, quiet and reasonably priced. I enjoyed my stay there immensely. A bonus was their convenient location."
United States
Jerrold
The price is P7,262
P14,100 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.

2. 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, (206 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is P14,060
P21,914 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 245 Newbury St
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

3. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.4 out of 10, Good, (26 reviews)
"Cute space! Wasn’t too difficult navigating Boston from this location."
United States
Rebecca
The price is P17,508
P28,035 total
includes taxes & fees
Oct 7 - Oct 8
The Concord Hotel
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

4. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (434 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is P8,388
P15,754 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 28 Fenway
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

5. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (490 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is P6,024
P10,879 total
includes taxes & fees
Nov 2 - Nov 3
Temple Place Suites
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

6. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (323 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 P15,482
P24,267 total
includes taxes & fees
Nov 1 - Nov 2
Kasa Boston at Fenway
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

7. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (39 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 P13,887
P23,872 total
includes taxes & fees
Oct 5 - Oct 6
The Chester Hotel
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

8. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,297 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is P9,514
P10,627 total
includes taxes & fees
Oct 31 - Nov 1
Crescent Suites Hotel
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

9. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (758 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is P11,147
P20,338 total
includes taxes & fees
Nov 1 - Nov 2
Global Luxury Suites Downtown Boston
A wooden hallway with a patterned floor leading to a door.

10. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (326 reviews)
"Room was clean, neat area."
United States
Keir
The price is P8,656
P15,258 total
includes taxes & fees
Oct 5 - Oct 6
Maverick Suites at 89 Marion
A modern hotel room with a bed, a desk, a sofa, and a dining area.

11. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (239 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is P14,324
P27,252 total
includes taxes & fees
Oct 13 - Oct 14
Charlesgate Suites
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 Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Quite a pleasant stay!"
Luke 1-night trip
Posted 3 hours ago
The Godfrey 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
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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.

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.