Winthrop Holiday Rentals

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Our top choices for Winthrop holiday rentals

10.0 out of 10, Exceptional, (53 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
The price is NZ$607
includes taxes & fees
22 Mar - 23 Mar
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Houseboat in Thompson Square - Bunker Hill

Charlestown Houseboat Walk to attractions Be rocked to sleep
9.6 out of 10, Exceptional, (101 reviews)
"Responsive host, amazing location, and refreshing change from a brick and mortar. "
United States
Larry N.
The price is NZ$683
includes taxes & fees
23 Mar - 24 Mar
Charlestown Houseboat Walk to attractions Be rocked to sleep
10.0 out of 10, Exceptional, (120 reviews)
"Overall our stay was good!"
United States
Yan B.
"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
3.5 star property
9.4 out of 10, Exceptional, (623 reviews)
"Hotel is in the perfect area to go to Faneuil hall as well as to the north end everything’s in walking distance multiple restaurants you can eat high-end or very inexpensive fun time for all"
United States
Cathy
The price is NZ$546
includes taxes & fees
22 Mar - 23 Mar
Marriott Vacation Club® at Custom House, Boston

Aparthotel in Bay Village

Bay Village Suites
2.0 star property
6.6 out of 10, (257 reviews)
"This is a convenient property, close to the T and the Common. You will need to be able to walk up some narrow stairs, and adjust to sharing a common bathroom. I met the owner while he was shoveling snow after the nor'easter, and he could not have been nicer! Great value for the money, fairly quiet and I would stay again."
United States
Louise
Bay Village Suites

Apartment in Downtown Boston

Temple Place Suites
2.5 star property
7.2 out of 10, Good, (338 reviews)
"Very spacious"
United States
Melany
The price is NZ$289
includes taxes & fees
22 Mar - 23 Mar
Temple Place Suites
The price is NZ$344
includes taxes & fees
26 Mar - 27 Mar
Enjoyable 2-bedroom lower level apartment in charming Lynn

Apartment in East Boston

Bright 2BR by Boston Waterfront
9.8 out of 10, Exceptional, (18 reviews)
"Perfect place for a Boston get away. Hosts are extremely polite, very transparent about parking. Very conveniently located to be anywhere in the city quickly. Will be staying here again in the future"
United States
Blāk R.
The price is NZ$408
includes taxes & fees
22 Mar - 23 Mar
Bright 2BR by Boston Waterfront
4.0 star property
8.0 out of 10, Very good, (670 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
Global Luxury Suites Downtown Boston
10.0 out of 10, Exceptional, (7 reviews)
"Great property!!!"
United States
Heather
The price is NZ$464
includes taxes & fees
24 Mar - 25 Mar
Hocus Pocus Season is here! Don’t miss it!

Aparthotel in Bay Village

Premier Suites - Bay Village
2.0 star property
6.2 out of 10, (260 reviews)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is NZ$401
includes taxes & fees
28 Mar - 29 Mar
Premier Suites - Bay Village

Apartment in Fenway–Kenmore

Maverick Suites at 28 Fenway
3.0 star property
8.6 out of 10, Excellent, (339 reviews)
"Good place"
United States
Elijah
The price is NZ$362
includes taxes & fees
22 Mar - 23 Mar
Maverick Suites at 28 Fenway
2.0 star property
7.4 out of 10, Good, (136 reviews)
"I couldn’t quite get the plug in stove to work. But overall it was an alright stay!!"
United States
Myah
Maverick Suites at 400 Columbus Ave

Aparthotel in South Side

Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (1,159 reviews)
"Dana’s customer service was excellent and my stay was as well. I will definitely stay again in the future."
United States
Sean
Crescent Suites Hotel
9.8 out of 10, Exceptional, (19 reviews)
"Space was clean with a personal touch for our stay. Matty made some great suggestions in and around Beverly/ Salem/ Boston. We loved the effort to make the stay feel welcoming."
United States
Miles G.
The price is NZ$414
includes taxes & fees
22 Mar - 23 Mar
Re-listed: Adorable Condo Beverly - Salem - Halloween

Aparthotel in Back Bay

Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very good, (160 reviews)
"Great location, clean and great 😌 "
United States
Catherine
Maverick Suites at 245 Newbury St
9.2 out of 10, Wonderful, (15 reviews)
"It was very clean, a great location, and the host was super responsive and helpful!"
United States
Kristen N.
The price is NZ$385
includes taxes & fees
22 Mar - 23 Mar
Central Salem Retreat 2bd W/ parking
9.8 out of 10, Exceptional, (24 reviews)
"Great place!"
United States
Jeffrey
The price is NZ$385
includes taxes & fees
22 Mar - 23 Mar
Salem Haunted Happenings Retreat
7.4 out of 10, Good, (10 reviews)
"Was clean and the location was perfect for my stay. "
United States
Laurie F.
The price is NZ$453
includes taxes & fees
23 Mar - 24 Mar
Cozy Studio Steps from Boston Common and Theaters
9.6 out of 10, Exceptional, (148 reviews)
"It was nice to rent a place for just one night. Great place. Spacious and clean. "
United States
Sue J.
The price is NZ$533
includes taxes & fees
13 Apr - 14 Apr
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
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 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 NZ$289 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?

Spacious, New Renovation | Near T: This holiday home rental outside of Winthrop is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 6 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?

Winthrop Beach and Massachusetts Bay are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include Fenway Park and Boston Harbor.

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.