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.
$235 nightly
The price is $263
Feb 8 - Feb 9
Total with taxes and fees
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.
$226 nightly
The price is $252
Feb 6 - Feb 7
Total with taxes and fees
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.
$342 nightly
The price is $393
Feb 9 - Feb 10
Total with taxes and fees
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, (200 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.
$411 nightly
The price is $472
Feb 6 - Feb 7
Total with taxes and fees
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.
$389 nightly
The price is $447
Feb 6 - Feb 7
Total with taxes and fees
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
$118 nightly
The price is $136
Feb 9 - Feb 10
Total with taxes and fees
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
$185 nightly
The price is $213
Feb 6 - Feb 7
Total with taxes and fees
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
$194 nightly
The price is $223
Feb 8 - Feb 9
Total with taxes and fees
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
$180 nightly
The price is $207
Feb 23 - Feb 24
Total with taxes and fees
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
$155 nightly
The price is $178
Feb 6 - Feb 7
Total with taxes and fees
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
$145 nightly
The price is $167
Feb 6 - Feb 7
Total with taxes and fees
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
$145 nightly
The price is $167
Feb 6 - Feb 7
Total with taxes and fees
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
$146 nightly
The price is $164
Feb 6 - Feb 7
Total with taxes and fees
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
$190 nightly
The price is $218
Feb 8 - Feb 9
Total with taxes and fees
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
$182 nightly
The price is $203
Feb 8 - Feb 9
Total with taxes and fees
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
$302 nightly
The price is $347
Feb 9 - Feb 10
Total with taxes and fees
Charlesgate Suites

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
$290 nightly
The price is $334
Feb 6 - Feb 7
Total with taxes and fees
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
$187 nightly
The price is $215
Feb 8 - Feb 9
Total with taxes and fees
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
$670 nightly
The price is $771
Feb 19 - Feb 20
Total with taxes and fees
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
$336 nightly
The price is $387
Feb 10 - Feb 11
Total with taxes and fees
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

Everything you need to know about Winthrop vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winthrop vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winthrop. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winthrop in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winthrop rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winthrop vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winthrop. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.