Winthrop Vacation Rentals

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Our top choices for Winthrop vacation 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.
$235 nightly
The price is $263
Mar 18 - Mar 19
Total with taxes and fees
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, (53 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
$297 nightly
The price is $331
Mar 18 - Mar 19
Total with taxes and fees
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (201 reviews)
"Perfect host, perfect spot, WORTH EVERY PENNY "
Canada
Jennifer E.
$448 nightly
The price is $515
Mar 24 - Mar 25
Total with taxes and fees
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (89 reviews)
"Our girls group enjoyed staying on this house boat. The marina is well situated to visit nearby attractions. Also, we had no trouble scheduling an Uber to pick us up from this location. The marina was safe as entry and exit was accomplished with a key fob. Also, we found the setting to be very peaceful and serene after a busy day in the city. "
United States
Wendy M.
$381 nightly
The price is $403
Mar 18 - Mar 19
Total with taxes and fees
Fun houseboat. Walk to Boston attractions WIFI

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, (101 reviews)
"Responsive host, amazing location, and refreshing change from a brick and mortar. "
United States
Larry N.
$343 nightly
The price is $395
Mar 18 - Mar 19
Total with taxes and fees
Charlestown Houseboat Walk to attractions Be rocked to sleep

Furnished Apartment near BMC

Furnished Apartment near BMC
3.0 star property
South End
$274 nightly
The price is $315
Mar 18 - Mar 19
Total with taxes and fees
Furnished Apartment near BMC

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
$317 nightly
The price is $365
Mar 23 - Mar 24
Total with taxes and fees
The Chester Hotel

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (334 reviews)
"Very spacious"
United States
Melany
$158 nightly
The price is $182
Mar 18 - Mar 19
Total with taxes and fees
Temple Place Suites

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
$109 nightly
The price is $120
Mar 18 - Mar 19
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn

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, (12 reviews)
"Beautiful place that made our vacation even better. There were so many hidden gems and the amenities were abundant. "
United States
Elizabeth
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway

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, (9 reviews)
"This location is so convenient to BU! Loved how easy check-in was!"
United States
Laura B.
$235 nightly
The price is $258
Mar 30 - Mar 31
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT

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.
$304 nightly
The price is $349
Mar 22 - Mar 23
Total with taxes and fees
Prime Central 1brm in North End Boston

Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (14 reviews)
"Great location- excellent place!"
United States
Deborah S.
$297 nightly
The price is $341
Mar 23 - Mar 24
Total with taxes and fees
Perfetto North End 1brm

*2BR Downtown Witch House|Salem+Beverly|Hospitals

*2BR Downtown Witch House|Salem+Beverly|Hospitals
Beverly
10.0 out of 10, Exceptional, (33 reviews)
"The home was nicely renovated and comfortable and our hosts were quick to respond to questions. Check in and out was easy and we had a nice stay and will return. "
United States
Lawrence D.
$301 nightly
The price is $336
Mar 18 - Mar 19
Total with taxes and fees
*2BR Downtown Witch House|Salem+Beverly|Hospitals

Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
Swampscott
8.4 out of 10, Very Good, (6 reviews)
"The view is amazing! Great communication with the host!"
United States
Bonnie V.
$521 nightly
The price is $556
Mar 18 - Mar 19
Total with taxes and fees
Coastal Charm: Lobster Châto

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, (47 reviews)
"very clean. comfortable beds. Very nice stay."
Germany
Stefanie K.
$300 nightly
The price is $335
Mar 22 - Mar 23
Total with taxes and fees
3BR pet-friendly Quincy house w/parking — near Adams Park

Re-listed: Adorable Condo Beverly - Salem - Halloween

Re-listed: Adorable Condo Beverly - Salem - Halloween
Beverly
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.
$222 nightly
The price is $247
Mar 22 - Mar 23
Total with taxes and fees
Re-listed: Adorable Condo Beverly - Salem - Halloween

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.4 out of 10, Very Good, (8 reviews)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
$291 nightly
The price is $313
Mar 25 - Mar 26
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential

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, (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
$279 nightly
The price is $321
Mar 22 - Mar 23
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston

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, (7 reviews)
"Great property!!!"
United States
Heather
$248 nightly
The price is $277
Mar 23 - Mar 24
Total with taxes and fees
Hocus Pocus Season is here! Don’t miss it!
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 $160 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?

Spacious, New Renovation | Near T: This vacation home rental near Winthrop is equipped with a barbecue grill, 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 you can cook with friends or family.

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 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.