Winthrop-Boston

Winthrop Vacation Rentals

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Our top choices for Winthrop vacation rentals

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (635 reviews)
"Excellent location and clean room with beautiful views. Very comfortable and convenient."
United States
Noelle
The price is CA $458
CA $526 total
includes taxes & fees
Jun 30 - Jul 1
Marriott Vacation Club® at Custom House, Boston

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
6.0 out of 10, (2 reviews)
The price is CA $545
CA $822 total
includes taxes & fees
Jun 25 - Jun 26
Furnished Apartment near BMC

The Concord Hotel

The Concord Hotel
2.0 star property
South End
10.0 out of 10, Exceptional, (1 review)
"Overall had a great experience here. Took just a couple minutes texting the host to get the check in information that was to be emailed- but they sent it pretty quickly when I said it wasn't sent yet. I didn't need anything else from the host. It was clean and overall pretty nice! The stairs you take to get up to the room are pretty loud, so I woke up one time when other people got home to other rooms during my stay, but that was it! Overall good. I was there for a holiday weekend so the price...
United States
Jessica
The price is CA $250
CA $467 total
includes taxes & fees
Jul 2 - Jul 3
The Concord Hotel

The Warlock House

The Warlock House
3.0 star property
Salem
The price is CA $1,300
CA $1,944 total
includes taxes & fees
Jun 29 - Jun 30
The Warlock House

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is CA $338
CA $893 total
includes taxes & fees
Jul 6 - Jul 7
Coastal Charm Lobster Ch Teau

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
The price is CA $234
CA $584 total
includes taxes & fees
Jun 27 - Jun 28
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,222 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
The price is CA $218
CA $243 total
includes taxes & fees
Jul 5 - Jul 6
Crescent Suites Hotel

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (708 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
The price is CA $218
CA $414 total
includes taxes & fees
Jul 1 - Jul 2
Global Luxury Suites Downtown Boston

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, (175 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is CA $229
CA $263 total
includes taxes & fees
Jun 30 - Jul 1
Maverick Suites at 245 Newbury St

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is CA $227
CA $441 total
includes taxes & fees
Jun 30 - Jul 1
The Chester Hotel

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.6 out of 10, Excellent, (17 reviews)
"Nice spot"
United States
Kimberly
The price is CA $389
CA $593 total
includes taxes & fees
Jun 25 - Jun 26
Furnished Apartments near Encore Boston

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (37 reviews)
"Excellent location, very easy check in process, clean, just as the pictures showed online."
United States
shannon
The price is CA $918
CA $1,300 total
includes taxes & fees
Jun 30 - Jul 1
The Monty Boston

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (396 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
The price is CA $171
CA $286 total
includes taxes & fees
Jul 6 - Jul 7
Temple Place Suites

Seacity View

Seacity View
2.0 star property
Swampscott
7.0 out of 10, Good, (2 reviews)
"Beautiful house!"
United States
carla n
The price is CA $810
CA $1,304 total
includes taxes & fees
Jul 19 - Jul 20
Seacity View

Lakeview Getaway With Hot Tub

Lakeview Getaway With Hot Tub
2.5 star property
Billerica
The price is CA $426
CA $1,007 total
includes taxes & fees
Jun 30 - Jul 1
Lakeview Getaway With Hot Tub

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (294 reviews)
"Great location and well maintained"
United States
EDDIE
The price is CA $171
CA $269 total
includes taxes & fees
Jul 1 - Jul 2
Premier Suites - Bay Village

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (156 reviews)
"Great location!"
United States
Kevin
The price is CA $234
CA $269 total
includes taxes & fees
Jun 30 - Jul 1
Maverick Suites at 400 Columbus Ave

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (289 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is CA $495
CA $716 total
includes taxes & fees
Jul 1 - Jul 2
Kasa Boston at Fenway

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (121 reviews)
"This was. A very nice, clean room. Plenty big enough for one or two people and great location, lots of dining and by the park"
United States
Rachel
The price is CA $263
CA $303 total
includes taxes & fees
Jun 28 - Jun 29
Maverick Suites at 40 Temple St

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (4 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is CA $267
CA $446 total
includes taxes & fees
Jul 2 - Jul 3
Symple Live
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

Find out more about Winthrop

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winthrop. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Boston's Best Vacation Home : This vacation home rental near Winthrop is equipped with a fireplace, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

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?

Point Shirley Beach and Winthrop Beach are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include Boston Harbor 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.