Winthrop Holiday Rentals

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Holiday Rentals in Winthrop

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches
9.8 out of 10, Exceptional, (6)
"Very good for the price, ideal location. Parking situation wasn't great, but otherwise was excellent."
United States
Ainsley S.
The price is AU$290
includes taxes & fees
13 Nov - 14 Nov
Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
10.0 out of 10, Exceptional, (52)
"Enjoyed my stay here. Good location. Clean place. Would stay here again."
United States
Charles V.
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
Fun houseboat. Walk to Boston attractions WIFI
9.8 out of 10, Exceptional, (88)
"This was such a lovely stay! The boat was very clean. Sherry, the property manager, made us feel welcome and had so much helpful information to offer. This location is very close to the ending of the freedom trail and walkable to so many famous sights. We were very comfortable and would definitely stay again! "
United States
Kevin S.
The price is AU$762
includes taxes & fees
3 Dec - 4 Dec
Fun houseboat. Walk to Boston attractions WIFI
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
9.8 out of 10, Exceptional, (199)
"What a great experience. We loved our stay. "
United States
Matt U.
The price is AU$803
includes taxes & fees
19 Nov - 20 Nov
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Spacious & Comfy 2BR/2Bath Yacht - Heat & AC - On Freedom Trail-Walk to Downtown
9.8 out of 10, Exceptional, (70)
"We all had a great time! Our two boys thought it was fun to sleep on a yacht! Chad was an excellent communicator! "
United States
Laura L.
The price is AU$825
includes taxes & fees
13 Nov - 14 Nov
Spacious & Comfy 2BR/2Bath Yacht - Heat & AC - On Freedom Trail-Walk to Downtown
Bay Village Suites
2.0 star property
6.4 out of 10, (241)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Maverick Suites at 400 Columbus Ave
2.0 star property
7.2 out of 10, Good, (129)
"Good location -comfortable "
United Kingdom
David
Maverick Suites at 400 Columbus Ave
Temple Place Suites
2.5 star property
7.0 out of 10, Good, (311)
"Very convenient place to stay, near transportation and waking distance to historic points and shopping. "
United States
Carolina
The price is AU$255
includes taxes & fees
1 Dec - 2 Dec
Temple Place Suites
Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (151)
"Good location, clean and quiet. Only thing that could be improved on would be luggage storage before check in "
United States
Kristee
Maverick Suites at 245 Newbury St
Maverick Suites at 40 Temple St
2.0 star property
7.6 out of 10, Good, (102)
"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
Premier Suites - Bay Village
2.0 star property
6.4 out of 10, (243)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is AU$269
includes taxes & fees
20 Nov - 21 Nov
Premier Suites - Bay Village
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very good, (618)
"The property looks much better inside than out Was just a couple of blocks to get to boston commons and T transportation. Staff was really nice "
United States
Teresa
Global Luxury Suites Downtown Boston
Maverick Suites at 89 Marion
2.0 star property
8.4 out of 10, Very good, (265)
"The kitchen isn't fully equipped for cooking. I found some culinary utensils incl. a pan and a pot. But there wasn't any stove to cook. The shops nearby are great incl. Trader Joe's and Maruichi. "
United States
Clare
Maverick Suites at 89 Marion
Best Location Studio In Downtown Boston
10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
The price is AU$392
includes taxes & fees
1 Dec - 2 Dec
Best Location Studio In Downtown Boston
The Chester Hotel
4.0 star property
8.6 out of 10, Excellent, (26)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is AU$589
includes taxes & fees
10 Nov - 11 Nov
The Chester Hotel
Maverick Suites at 28 Fenway
3.0 star property
8.8 out of 10, Excellent, (307)
"Spotless room, spotless building, great staff, comfortable bed. "
United States
Patricia
The price is AU$331
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 28 Fenway
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
4.0 star property
8.8 out of 10, Excellent, (276)
"Easy check in and clean property with in unit laundry"
United States
Sarah
The price is AU$285
includes taxes & fees
3 Dec - 4 Dec
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Amazing price & location w parking -North End -Boston
9.6 out of 10, Exceptional, (57)
"Can't beat location and price, walkable to everything. Would stay again. Small place, but all we needed and was as advertised. "
United States
Micki F.
The price is AU$591
includes taxes & fees
29 Nov - 30 Nov
Amazing price & location w parking -North End -Boston
The Chester: Penthouse One Bedroom
2.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely loved my stay. Great location, beautiful place. Clean and bright. We will be back!"
United States
Linda C.
The price is AU$669
includes taxes & fees
16 Nov - 17 Nov
The Chester: Penthouse One Bedroom
Modern North End Studio
9.0 out of 10, Wonderful, (10)
"Really cute, clean, and awesome location!"
United States
Carrie T.
The price is AU$543
includes taxes & fees
11 Nov - 12 Nov
Modern North End Studio
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winthrop holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winthrop holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winthrop holiday rentals we have selected for you start as low as AU$237 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop holiday 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 holiday.

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 holiday rental in Winthrop?

Yes, we give you a choice of holiday rentals where you'll be only 3.7 mi (6 km) from New England Aquarium, providing 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 cafés and waterfront during your trip.

What are some of the best holiday rentals that Winthrop has to offer?

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston: This holiday home rental outside of Winthrop is located in the city centre, and has a patio, a selection of games and air conditioning to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Winthrop?

With 4 Expedia holiday rentals, you're guaranteed 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 New England Aquarium and TD Garden.

What are holiday rentals like in Winthrop?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winthrop. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip.