Winthrop-Boston

Winthrop Holiday Rentals

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Our top choices for Winthrop holiday 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, (55 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
The price is NZ$714
includes taxes & fees
28 June - 29 June
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (96 reviews)
"Great location, very clean, very safe, beautiful view of the city when walking. Definitely would recommend ~"
United States
Tracey
The price is NZ$941
includes taxes & fees
16 July - 17 July
Fun houseboat. Walk to Boston attractions WIFI

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
9.4 out of 10, Exceptional, (105 reviews)
"host was so welcoming and we enjoyed they stay"
United States
Roshawn D.
The price is NZ$1,168
includes taxes & fees
1 July - 2 July
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (392 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
The price is NZ$351
includes taxes & fees
21 June - 22 June
Temple Place Suites

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (3 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is NZ$560
includes taxes & fees
24 June - 25 June
Symple Live

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.4 out of 10, Very good, (6 reviews)
"Would stay again"
United States
mark p.
The price is NZ$482
includes taxes & fees
21 June - 22 June
Studio Awaits Your Next Stay!

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.6 out of 10, Exceptional, (10 reviews)
The price is NZ$461
includes taxes & fees
14 July - 15 July
Enjoyable 2-bedroom lower level apartment in charming Lynn

Bright 1 Bedroom | Downtown Boston

Bright 1 Bedroom | Downtown Boston
Bay Village
10.0 out of 10, Exceptional, (1 review)
"Great location to explore Boston with your dogs"
Canada
Thiery
The price is NZ$583
includes taxes & fees
6 July - 7 July
Bright 1 Bedroom | Downtown Boston

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (292 reviews)
"Great location and well maintained"
United States
EDDIE
The price is NZ$331
includes taxes & fees
24 June - 25 June
Premier Suites - Bay Village

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"It was a great stay!"
United States
Adina S.
The price is NZ$430
includes taxes & fees
6 July - 7 July
Light-filled Studio | Back Bay

Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport

Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport
Downtown Boston
9.4 out of 10, Exceptional, (3 reviews)
"Location was awesome and central to the attractions. "
United States
Shelly B.
The price is NZ$845
includes taxes & fees
2 July - 3 July
Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport

The Concord Hotel

The Concord Hotel
2.0 star property
South End
The price is NZ$547
includes taxes & fees
21 June - 22 June
The Concord Hotel

Primo North End Studio

Primo North End Studio
North End
9.2 out of 10, Wonderful, (15 reviews)
"Great place, amazing location!"
United States
Christopher W.
Primo North End Studio

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (82 reviews)
"Host was amazing and responded right away with any questions or concerns we had! Beautiful place to stay!"
United States
Amy I.
The price is NZ$643
includes taxes & fees
14 July - 15 July
🎖The Boiler Room - Close to Subway & Downtown🎖

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
The price is NZ$563
includes taxes & fees
24 June - 25 June
Beautiful 1BR near Fenway Park + Kenmore!

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.8 out of 10, Excellent, (11 reviews)
"Excellent location for restaurants, shops, sightseeing. Lovely buzz around the area, with park & river close by to escape if necessary. Large lounge area to put your feet up between trips, and adequate glasses etc for drinks and nibbles between the treats at the bakeries and restaurants nearby."
United Kingdom
Jude
The price is NZ$714
includes taxes & fees
1 July - 2 July
Stylish Back Bay Retreat, Steps from Prudential

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.4 out of 10, Very good, (23 reviews)
"Friendly hosts"
United States
Jan
The price is NZ$568
includes taxes & fees
30 June - 1 July
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly

Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly
Wilmington
The price is NZ$1,047
includes taxes & fees
30 June - 1 July
Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very good, (44 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
The price is NZ$537
includes taxes & fees
30 June - 1 July
On River/Harvard Sq. two blocks

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is NZ$539
includes taxes & fees
21 June - 22 June
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winthrop holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winthrop. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winthrop. Seeing all the best attractions is bound to make you fall in love with Winthrop. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winthrop short-term rentals, that won’t be hard to do.

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?

Boston's Best Vacation Home : This holiday home rental outside of Winthrop is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay.

How many holiday rentals are there in Winthrop?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

Point Shirley Beach 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 Boston Harbor 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.