Holiday Rentals in Winthrop

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Our top choices for Winthrop holiday rentals

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 €210
includes taxes & fees
28 Jan - 29 Jan
Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

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)
"Owner was easy to communicate with. "
Canada
Ronald
The price is €359
includes taxes & fees
9 Feb - 10 Feb
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by

Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
Thompson Square - Bunker Hill
10.0 out of 10, Exceptional, (57 reviews)
"We loved the unique setting, kind and helpful hosts, and tasty breakfast. Made us feel like we were “wicked smaht” for booking!"
United States
Jayson M.
The price is €396
includes taxes & fees
18 Jan - 19 Jan
Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by

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)
"Great location, pet friendly, "
United States
Karen W.
The price is €376
includes taxes & fees
18 Jan - 19 Jan
Charlestown Houseboat Walk to attractions Be rocked to sleep

Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard

Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
Charlestown
10.0 out of 10, Exceptional, (241 reviews)
"Had a wonderful time and staying in the harbor was a great way to see Boston and surrounding area.Parking was easy, house boat was fabulous, owners were easy to deal with, and property manager gave us some great tips! Overall.... 10 out of 10!"
United States
bill w.
The price is €400
includes taxes & fees
25 Jan - 26 Jan
Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (643 reviews)
"Place was perfect and very convenient. Staff was nice and very helpful. Definitely booking again "
United States
Rudolfo
Global Luxury Suites Downtown Boston

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (335 reviews)
"Good place"
United States
Elijah
The price is €177
includes taxes & fees
18 Jan - 19 Jan
Maverick Suites at 28 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, (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

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 €298
includes taxes & fees
18 Jan - 19 Jan
Charlesgate Suites

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (68 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

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (329 reviews)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is €114
includes taxes & fees
17 Jan - 18 Jan
Temple Place Suites

Luxury 1 bedroom downtown appartment

Luxury 1 bedroom downtown appartment
2.0 star property
Government Center
10.0 out of 10, Exceptional, (4 reviews)
"Gorgeous apartment with unmatched views. Dina is such a welcoming and gracious host and we had everything we needed. "
United States
Sarah D.
The price is €458
includes taxes & fees
25 Jan - 26 Jan
Luxury 1 bedroom downtown appartment

North End Entire House

North End Entire House
North End
10.0 out of 10, Exceptional, (15 reviews)
"The house was very clean and in a great location. The host was very responsive throughout the booking and stay. "
United States
Jenn C.
The price is €478
includes taxes & fees
19 Jan - 20 Jan
North End Entire House

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 €169
includes taxes & fees
29 Jan - 30 Jan
Premier Suites - Bay Village

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 €269
includes taxes & fees
18 Jan - 19 Jan
The Chester Hotel

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Beacon Hill
10.0 out of 10, Exceptional, (21 reviews)
"Great location, highly recommend it!"
United States
Aimee S.
The price is €703
includes taxes & fees
19 Jan - 20 Jan
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

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, (156 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

Bay Village Suites

Bay Village Suites
2.0 star property
Bay Village
6.6 out of 10, (252 reviews)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites

The Chester: Penthouse One Bedroom

The Chester: Penthouse One Bedroom
2.0 star property
South End
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely loved my stay. Great location, beautiful place. Clean and bright. We will be back!"
United States
Linda C.
The price is €378
includes taxes & fees
19 Jan - 20 Jan
The Chester: Penthouse One Bedroom

3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (4 reviews)
"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "
United States
mary j.
The price is €518
includes taxes & fees
19 Jan - 20 Jan
3BR3Bth Entire House/Steps to Downtown & TD Garden
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, apart-hotels, 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 favorite 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 depends 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 €114 per night. Entering your travel dates in the search wizard you might find 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?

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi: This holiday home rental outside of Winthrop is located in the city centre, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 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 TD Garden and Fenway Park.

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.