Winthrop Vacation Rentals

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Our top choices for Winthrop vacation rentals

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
Winthrop
10.0 out of 10, Exceptional, (52 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
The price is CA $134
CA $341 total
includes taxes & fees
Feb 8 - Feb 9
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches
Winthrop
9.6 out of 10, Exceptional, (7 reviews)
"Great location and wonderful hosts! Would definitely recommend to anyone staying in the Boston area. "
United States
Kristie P.
The price is CA $90
CA $245 total
includes taxes & fees
Feb 8 - Feb 9
Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

Charlestown Houseboat Walk to attractions Be rocked to sleep

Charlestown Houseboat Walk to attractions Be rocked to sleep
Thompson Square - Bunker Hill
9.6 out of 10, Exceptional, (99 reviews)
"Responsive host, amazing location, and refreshing change from a brick and mortar. "
United States
Larry N.
The price is CA $82
CA $530 total
includes taxes & fees
Feb 10 - Feb 11
Charlestown Houseboat Walk to attractions Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (201 reviews)
"My husband and I had an excellent stay! It was very comfortable! I would highly recommend staying on The Blue Pearl and hope to stay there again. "
United States
Stacey W.
The price is CA $123
CA $634 total
includes taxes & fees
Feb 8 - Feb 9
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (89 reviews)
"Such a unique experience.We loved the relaxing views after a long day of site seeing.Great access to sites and airport."
United States
Laura M.
The price is CA $137
CA $597 total
includes taxes & fees
Feb 8 - Feb 9
Fun houseboat. Walk to Boston attractions WIFI

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (656 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
The price is CA $115
CA $194 total
includes taxes & fees
Feb 18 - Feb 19
Global Luxury Suites Downtown Boston

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.2 out of 10, Good, (135 reviews)
"everything was great! only thing i’ll say is that the dots have some cracks where people can see in on the bathrooms and some rooms, but other than that i’d start here again!"
United States
Maelynn
The price is CA $130
CA $275 total
includes taxes & fees
Feb 8 - Feb 9
Maverick Suites at 400 Columbus Ave

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, (157 reviews)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (103 reviews)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
Maverick Suites at 40 Temple St

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (331 reviews)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is CA $112
CA $215 total
includes taxes & fees
Feb 8 - Feb 9
Temple Place Suites

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (257 reviews)
"We stayed there for four days. The heaters were not working, I got almost sick. And the customer service was awful. I hope you will find better place to stay"
United States
Aziza
The price is CA $105
CA $191 total
includes taxes & fees
Feb 8 - Feb 9
Premier Suites - Bay Village

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (253 reviews)
"Great location nice neighborhood "
United States
Jose
The price is CA $105
CA $191 total
includes taxes & fees
Feb 12 - Feb 13
Bay Village Suites

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,151 reviews)
"Everything about this facility was pleasing: clean, well-appointed, great kitchen, comfortable, well-located in the area. We were given a warm welcome when we arrived, provided with lots of information about Waltham. Located near shops and restaurants and on a walking trail along the Charles River. Highly recommend and would stay here again. "
Canada
Susan
Crescent Suites Hotel

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (337 reviews)
"Good place"
United States
Elijah
The price is CA $129
CA $282 total
includes taxes & fees
Feb 8 - Feb 9
Maverick Suites at 28 Fenway

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner South Side
8.2 out of 10, Very good, (271 reviews)
"The room was very clean and perfectly sized for a solo traveler for several nights."
United States
Valeri
The price is CA $126
CA $262 total
includes taxes & fees
Feb 8 - Feb 9
Maverick Suites at 89 Marion

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (201 reviews)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is CA $208
CA $475 total
includes taxes & fees
Feb 11 - Feb 12
Charlesgate Suites

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
The price is CA $128
CA $337 total
includes taxes & fees
Feb 8 - Feb 9
Furnished Apartment near BMC

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, (69 reviews)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 Columbus Ave

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (32 reviews)
"Amazing property, would stay again."
United States
Doug
The price is CA $697
CA $1,038 total
includes taxes & fees
Feb 8 - Feb 9
The Monty Boston

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28 reviews)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is CA $212
CA $487 total
includes taxes & fees
Feb 11 - Feb 12
The Chester 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

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?

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino: This vacation home rental near Winthrop is located on the waterfront and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Winthrop?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

Boston Harbor Islands State Park 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 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.