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, (52 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
$264 nightly
The price is $295
Feb 22 - Feb 23
Total with taxes and fees
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

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.
$212 nightly
The price is $236
Feb 17 - Feb 18
Total with taxes and fees
Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (618 reviews)
"I can’t recommend The Custom House enough, it is perfect! The staff are wonderful, it’s very clean and the perfect location to see Boston! "
United States
Melissa
$175 nightly
The price is $201
Feb 22 - Feb 23
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston

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)
"We had a great stay! We enjoyed the area and our house boat experience. Would definitely come back in the future and recommend to others "
United States
Winona S.
$398 nightly
The price is $457
Feb 17 - Feb 18
Total with taxes and fees
Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard

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
$321 nightly
The price is $369
Feb 17 - Feb 18
Total with taxes and fees
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.
$695 nightly
The price is $799
Feb 17 - Feb 18
Total with taxes and fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Ocean Dreams, Waves as far as the eyes can see...........

Ocean Dreams, Waves as far as the eyes can see...........
Scituate
9.8 out of 10, Exceptional, (158 reviews)
"Beautiful beach house with everything we needed and the location can’t be beat. Hope to stay again the next time I’m looking for ocean views and beach time!"
United States
Elise T.
$953 nightly
The price is $1,045
Feb 17 - Feb 18
Total with taxes and fees
Ocean Dreams, Waves as far as the eyes can see...........

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (658 reviews)
"Everything was great about this place! I will definitely be staying here again!"
United States
Amanda
$144 nightly
The price is $165
Mar 1 - Mar 2
Total with taxes and fees
Global Luxury Suites Downtown Boston

King Bed Loft in the Heart of Downtown Boston

King Bed Loft in the Heart of Downtown Boston
Downtown Boston
10.0 out of 10, Exceptional, (38 reviews)
"It was my first time staying here, and the room was very clean and fresh. The staff were extremely friendly and helpful, and the facilities were perfect. I will definitely stay here again, and I highly recommend it to anyone."
Japan
MINEKI
$603 nightly
The price is $693
Feb 17 - Feb 18
Total with taxes and fees
King Bed Loft in the Heart of Downtown Boston

Luxury 1 bedroom downtown appartment

Luxury 1 bedroom downtown appartment
Government Center
10.0 out of 10, Exceptional, (5 reviews)
"This was absolutely phenomenal!! The apartment is immaculate, and the common areas are fabulous!! We used the outdoor deck and billiards table (on the 32nd floor, same floor the apartment is on.) Also, the "walk to all" location is great.Best of all, the unobstructed view is jaw dropping. Dina, the host, is delightful. Highly recommend this!!!"
United States
Paul G.
$513 nightly
The price is $590
Mar 12 - Mar 13
Total with taxes and fees
Luxury 1 bedroom downtown appartment

Lake Access 4 Bed 3 Full Bath

Lake Access 4 Bed 3 Full Bath
Billerica
9.8 out of 10, Exceptional, (22 reviews)
"The house was perfect for us! Sparkling clean and comfortable. We really enjoyed staying here and would stay again for sure!"
United States
Diane B.
$656 nightly
The price is $705
Feb 17 - Feb 18
Total with taxes and fees
Lake Access 4 Bed 3 Full Bath

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

3BR pet-friendly Quincy house w/parking — near Adams Park
Quincy
9.6 out of 10, Exceptional, (44 reviews)
"very clean. comfortable beds. Very nice stay."
Germany
Stefanie K.
$294 nightly
The price is $329
Feb 17 - Feb 18
Total with taxes and fees
3BR pet-friendly Quincy house w/parking — near Adams Park

14a-Cozy and well decorated apartment in awesome Boston

14a-Cozy and well decorated apartment in awesome Boston
Dorchester
10.0 out of 10, Exceptional, (27 reviews)
"Very nice home and convenient to local restaurants and bakery. Also easy to get to downtown Boston. "
United States
Frank M.
$346 nightly
The price is $398
Feb 17 - Feb 18
Total with taxes and fees
14a-Cozy and well decorated apartment in awesome Boston

North End Entire House

North End Entire House
North End
10.0 out of 10, Exceptional, (16 reviews)
"Great location in the Northend!"
United States
Carol T.
$445 nightly
The price is $512
Feb 19 - Feb 20
Total with taxes and fees
North End Entire House

Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.8 out of 10, Exceptional, (18 reviews)
"Overall comfortable stay"
United States
Jolly J.
$182 nightly
The price is $203
Feb 17 - Feb 18
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in superb Canton

1880 updated Victorian 1st floor, water views

1880 updated Victorian 1st floor, water views
Salem
10.0 out of 10, Exceptional, (5 reviews)
"Constantly kept an open line of communication, very accommodating and kind. We were here for 4 days and couldn’t have found a better host or place to stay if we tried. Got so lucky with Carol we’ll be forever grateful "
United States
Brian G.
$206 nightly
The price is $230
Feb 17 - Feb 18
Total with taxes and fees
1880 updated Victorian 1st floor, water views

Relax with family or friends to this elegant apartment in the heart of Waltham

Relax with family or friends to this elegant apartment in the heart of Waltham
South Side
9.6 out of 10, Exceptional, (18 reviews)
"We had a wonderful time!"
United States
Paul H.
$474 nightly
The price is $529
Feb 17 - Feb 18
Total with taxes and fees
Relax with family or friends to this elegant apartment in the heart of Waltham

Entire Lower Level of the House, Across From The Beach

Entire Lower Level of the House, Across From The Beach
Swampscott
9.8 out of 10, Exceptional, (25 reviews)
"Wonderful place! Diana was a wonderful host and provided everything we needed for a cozy stay on our girls trip!"
United States
Dana F.
$318 nightly
The price is $355
Feb 24 - Feb 25
Total with taxes and fees
Entire Lower Level of the House, Across From The Beach

1 Mi to Downtown Salem: Studio w/ Fire Pit Access

1 Mi to Downtown Salem: Studio w/ Fire Pit Access
3.0 star property
Salem
9.6 out of 10, Exceptional, (5 reviews)
"Studio was very nicely laid out and the owner of the property was friendly! Area the house was in was quiet but yet still walkable to downtown Salem. Bagel place across the street was amazing as well"
United States
chris
$315 nightly
The price is $352
Feb 18 - Feb 19
Total with taxes and fees
1 Mi to Downtown Salem: Studio w/ Fire Pit Access

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Entire 4BR 2 Bath Home l Minutes to Downtown Salem
Salem
10.0 out of 10, Exceptional, (18 reviews)
"Our stay was fantastic. Great location, only an 8 minute walk to Essex st. Great host as well! "
United States
Adam R.
$347 nightly
The price is $388
Feb 17 - Feb 18
Total with taxes and fees
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
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 vacation rentals

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

Winthrop vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winthrop in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $162 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop vacation 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 vacation.

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 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?

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino: This vacation home rental near Winthrop is located on the waterfront and has a fireplace, a patio, and air-conditioning to put you at ease 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. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Winthrop?

With 4 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 Massachusetts Bay 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 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.