Winthrop Vacation Rentals

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Our top choices for Winthrop vacation 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, (53 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
The price is CA $239
CA $478 total
includes taxes & fees
May 27 - May 28
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, (94 reviews)
"Great location, very clean, very safe, beautiful view of the city when walking. Definitely would recommend ~"
United States
Tracey
The price is CA $182
CA $652 total
includes taxes & fees
May 10 - May 11
Fun houseboat. Walk to Boston attractions WIFI

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is CA $226
CA $433 total
includes taxes & fees
May 10 - May 11
The Chester Hotel

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very good, (41 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
The price is CA $233
CA $428 total
includes taxes & fees
May 10 - May 11
On River/Harvard Sq. two blocks

2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (20 reviews)
"Location and amenities were great! Close to everything , yet private. Comfortable and clean . Host was most helpful.Will definitely try to stay again when traveling to the area ."
United States
George G.
The price is CA $139
CA $487 total
includes taxes & fees
May 11 - May 12
2BR Historic Marblehead Home+Minutes to Beach

Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (25 reviews)
"Location was ideal and property was well-kept and organized. Definitely would recommend for future visits."
United States
Taye A.
The price is CA $226
CA $522 total
includes taxes & fees
May 25 - May 26
Prime Central 1brm in North End Boston

3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (10 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 CA $222
CA $645 total
includes taxes & fees
May 26 - May 27
3BR3Bth Entire House/Steps to Downtown & TD Garden

Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
10.0 out of 10, Exceptional, (26 reviews)
"Great property to stay with proximity to everything you need, and a safe neighborhood to walk all times of the day. The hosts were very communicative and quick to respond to any questions I had. The apartment itself was spacious and had a nice kitchen to prepare meals. I would recommend to all considering a stay in East Boston!"
United States
Jordan
The price is CA $135
CA $349 total
includes taxes & fees
May 11 - May 12
Bright 2BR by Boston Waterfront

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking
Beverly
9.2 out of 10, Wonderful, (24 reviews)
"Cheerful decor, well-equipped kitchen, and clean. Good location in walking distance to restaurants. However, there was a musty smell throughout the building and rooms. "
United States
Julia
The price is CA $154
CA $417 total
includes taxes & fees
May 11 - May 12
Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Blissful South End Studio

Blissful South End Studio
Back Bay
9.4 out of 10, Exceptional, (3 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is CA $145
CA $359 total
includes taxes & fees
May 18 - May 19
Blissful South End Studio

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (113 reviews)
"A phenomenal stay at maverick suites! The location was fantastic, the room was spotless and cozy, and the check-in/out process was a breeze. I’d happily stay here again and recommend to anyone taking a trip to Boston!"
United States
Kendra
The price is CA $172
CA $323 total
includes taxes & fees
May 10 - May 11
Maverick Suites at 40 Temple St

Hocus Pocus Season is here! Don’t miss it!

Hocus Pocus Season is here! Don’t miss it!
Salem
10.0 out of 10, Exceptional, (9 reviews)
"Great property!!!"
United States
Heather
The price is CA $155
CA $424 total
includes taxes & fees
May 11 - May 12
Hocus Pocus Season is here! Don’t miss it!

Primo North End Studio

Primo North End Studio
North End
9.2 out of 10, Wonderful, (14 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is CA $253
CA $533 total
includes taxes & fees
May 10 - May 11
Primo North End Studio

3BR pet-friendly Quincy house w/parking — near Adams Park

3BR pet-friendly Quincy house w/parking — near Adams Park
Quincy
9.8 out of 10, Exceptional, (49 reviews)
"very clean. comfortable beds. Very nice stay."
Germany
Stefanie K.
The price is CA $185
CA $493 total
includes taxes & fees
May 10 - May 11
3BR pet-friendly Quincy house w/parking — near Adams Park

Bee-Themed Stay Near Boston – A Sweet and Unique Getaway

Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Billerica
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful place that made our vacation even better. There were so many hidden gems and the amenities were abundant. "
United States
Elizabeth
The price is CA $148
CA $272 total
includes taxes & fees
May 21 - May 22
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway

Cozy three-bedroom home close to Boston w/ plenty of parking

Cozy three-bedroom home close to Boston w/ plenty of parking
North Braintree
10.0 out of 10, Exceptional, (47 reviews)
"The house was just what we needed and the stay was super simple. "
United States
Chris B.
The price is CA $259
CA $603 total
includes taxes & fees
May 10 - May 11
Cozy three-bedroom home close to Boston w/ plenty of parking

Exquisite North End 1brm

Exquisite North End 1brm
North End
9.6 out of 10, Exceptional, (34 reviews)
"Location was ideal "
Canada
Lindsay
The price is CA $239
CA $539 total
includes taxes & fees
May 25 - May 26
Exquisite North End 1brm

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.4 out of 10, Exceptional, (6 reviews)
The price is CA $177
CA $331 total
includes taxes & fees
May 12 - May 13
Enjoyable 2-bedroom lower level apartment in charming Lynn

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very good, (14 reviews)
"Great location, check in and check out was easy. Clean space. Great value "
United States
David
The price is CA $194
CA $383 total
includes taxes & fees
May 18 - May 19
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
Marblehead
10.0 out of 10, Exceptional, (27 reviews)
"great place and location"
United States
Kacey C.
The price is CA $339
CA $603 total
includes taxes & fees
Jun 8 - Jun 9
Bright & Stylish Coastal Retreat in Marblehead Historic Center w 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.
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Top Winthrop Hotel Reviews

Find out more about Winthrop

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

Centrally located in the heart of Boston near T: This vacation home near Winthrop has air-conditioning and laundry facilities to help you feel perfectly comfortable 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.

How many vacation rentals are there in Winthrop?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

Winthrop Beach and Point Shirley Beach 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 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.