Winthrop Vacation Rentals

Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Winthrop vacation rentals

Interior

Apartment in Winthrop

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches
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.
$202 nightly
The price is $225
Jan 27 - Jan 28
Total with taxes and fees
Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches
Exterior

Houseboat in Charlestown

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
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.
$375 nightly
The price is $431
Jan 27 - Jan 28
Total with taxes and fees
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Property grounds

Houseboat in Thompson Square - Bunker Hill

Charlestown Houseboat Walk to attractions Be rocked to sleep
9.6 out of 10, Exceptional, (99 reviews)
"Great location, pet friendly, "
United States
Karen W.
$354 nightly
The price is $407
Feb 1 - Feb 2
Total with taxes and fees
Charlestown Houseboat Walk to attractions Be rocked to sleep
Interior

Houseboat in Boston

Fun houseboat. Walk to Boston attractions WIFI
9.8 out of 10, Exceptional, (89 reviews)
"It was unique way to stay in the city"
United States
brian m.
$360 nightly
The price is $381
Jan 29 - Jan 30
Total with taxes and fees
Fun houseboat. Walk to Boston attractions WIFI
Lobby lounge

Aparthotel in Chinatown

Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (653 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
$118 nightly
The price is $136
Feb 1 - Feb 2
Total with taxes and fees
Global Luxury Suites Downtown Boston
Exterior

Aparthotel in Back Bay

Maverick Suites at 245 Newbury St
2.0 star property
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
$180 nightly
The price is $207
Jan 28 - Jan 29
Total with taxes and fees
Maverick Suites at 245 Newbury St
Apartment, 2 Bedrooms | Interior

Apartment in South End

Furnished Apartment near BMC
3.0 star property
$238 nightly
The price is $273
Jan 27 - Jan 28
Total with taxes and fees
Furnished Apartment near BMC
Front of property

Aparthotel in Beacon Hill

Maverick Suites at 40 Temple St
2.0 star property
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
$194 nightly
The price is $223
Jan 27 - Jan 28
Total with taxes and fees
Maverick Suites at 40 Temple St
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Downtown Boston

Boston Financial District 1BR | Walk to anything!
$224 nightly
The price is $263
Feb 2 - Feb 3
Total with taxes and fees
Boston Financial District 1BR | Walk to anything!
42-inch TV with satellite channels

Aparthotel in South End

Maverick Suites at 400 Columbus Ave
2.0 star property
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 1 - Feb 2
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Apartment in Downtown Boston

Temple Place Suites
2.5 star property
7.0 out of 10, Good, (331 reviews)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
$155 nightly
The price is $178
Jan 27 - Jan 28
Total with taxes and fees
Temple Place Suites
Premium Apartment | Living area | 24-inch Smart TV with digital channels

Aparthotel in South End

The Chester Hotel
4.0 star property
8.6 out of 10, Excellent, (28 reviews)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
$321 nightly
The price is $369
Feb 3 - Feb 4
Total with taxes and fees
The Chester Hotel
Exterior

Apartment in Downtown Boston

Best Location Studio In Downtown Boston
10.0 out of 10, Exceptional, (1 review)
"In town to celebrate a special event."
United States
Pam P.
$193 nightly
The price is $227
Feb 1 - Feb 2
Total with taxes and fees
Best Location Studio In Downtown Boston
Desk, laptop workspace, free WiFi, bed sheets

Aparthotel in Bay Village

Bay Village Suites
2.0 star property
6.6 out of 10, (252 reviews)
"Great location nice neighborhood "
United States
Jose
$145 nightly
The price is $167
Jan 27 - Jan 28
Total with taxes and fees
Bay Village Suites
Exterior detail

Condo in Beacon Hill

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
10.0 out of 10, Exceptional, (2 reviews)
"Had a wonderful stay! Beautiful condo in a beautiful neighborhood that is walking distance to the commons."
United States
Grant T.
$234 nightly
The price is $269
Feb 2 - Feb 3
Total with taxes and fees
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Aparthotel in Bay Village

Premier Suites - Bay Village
2.0 star property
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
$133 nightly
The price is $153
Jan 27 - Jan 28
Total with taxes and fees
Premier Suites - Bay Village
Fridge, microwave, oven, stovetop

Vacation Home in North End

3BR3Bth Entire House/Steps to Downtown & TD Garden
10.0 out of 10, Exceptional, (5 reviews)
"Clean and bright throughout, host was great with timely responses to all inquiries. Maybe not the best for young children bc of the all the stairs (which are beautiful btw)."
United States
Margaret S.
$473 nightly
The price is $544
Jan 29 - Jan 30
Total with taxes and fees
3BR3Bth Entire House/Steps to Downtown & TD Garden
1 bedroom, desk, iron/ironing board, WiFi

Apartment in Bay Village

Studio Awaits Your Next Stay!
9.2 out of 10, Wonderful, (5 reviews)
"Would stay again"
United States
mark p.
$193 nightly
The price is $227
Jan 27 - Jan 28
Total with taxes and fees
Studio Awaits Your Next Stay!
1 bedroom, desk, iron/ironing board, WiFi

Apartment in Downtown Boston

Perfect One Bedroom Stay In Downtown Boston!
8.6 out of 10, Excellent, (18 reviews)
"Temple Place Suites was a great place to stay for our few days in Boston. We loved being across from Boston Commons, near great bakerys and cafes. It was a comfortable apartment with great space and plenty of amenities. Staff was great at communicating about check in, building codes and check out. Wished there were dish towels and wash cloths. Otherwise, it was great!!"
United States
Christine
$197 nightly
The price is $231
Jan 27 - Jan 28
Total with taxes and fees
Perfect One Bedroom Stay In Downtown Boston!
Marina

Condo in Marblehead

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
10.0 out of 10, Exceptional, (71 reviews)
"The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again."
United States
Pamela O.
$208 nightly
The price is $232
Jan 27 - Jan 28
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
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 Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Every single staff member I interacted with was very friendly and helpful. The entire hotel was lovely and clean, including my room. The on site restaurant, bar, and coffee spot were all great as well and overall contributed to an excellent experience. "
Hunter 2-night trip
Posted 12 hours ago
The Godfrey Hotel Boston

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.

Explore a world of travel with Expedia

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.