A coastal town with a lighthouse, sandy beach, and residential buildings.

Winthrop Vacation Rentals

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Our top choices for Winthrop vacation rentals

Beautiful 3-bedroom apartment with AC in welcoming Winthrop

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
The price is CA $406
CA $592 total
includes taxes & fees
Jul 13 - Jul 14
Beautiful 3-bedroom apartment with AC in welcoming Winthrop

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 CA $287
CA $545 total
includes taxes & fees
Jun 28 - Jun 29
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

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, (637 reviews)
"Excellent location and clean room with beautiful views. Very comfortable and convenient."
United States
Noelle
The price is CA $445
CA $512 total
includes taxes & fees
Jun 30 - Jul 1
Marriott Vacation Club® at Custom House, Boston

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (378 reviews)
"Great stay. "
United States
Anna
The price is CA $129
CA $287 total
includes taxes & fees
Jul 1 - Jul 2
Maverick Suites at 28 Fenway

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (295 reviews)
"Great location and well maintained"
United States
EDDIE
The price is CA $139
CA $234 total
includes taxes & fees
Jul 5 - Jul 6
Premier Suites - Bay Village

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (176 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is CA $183
CA $210 total
includes taxes & fees
Jun 30 - Jul 1
Maverick Suites at 245 Newbury St

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (396 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 CA $139
CA $250 total
includes taxes & fees
Jun 28 - Jun 29
Temple Place Suites

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (3 reviews)
"It was a great stay!"
United States
Adina S.
The price is CA $122
CA $366 total
includes taxes & fees
Jul 5 - Jul 6
Light-filled Studio | Back Bay

5 Mi to Salem: Furnished Patio at Danvers Studio!

5 Mi to Salem: Furnished Patio at Danvers Studio!
Danvers
9.8 out of 10, Exceptional, (26 reviews)
"Perfect stay!"
Canada
Billee
The price is CA $146
CA $322 total
includes taxes & fees
Jul 24 - Jul 25
5 Mi to Salem: Furnished Patio at Danvers Studio!

Dwtn Beverly! 5 Min to Salem!

Dwtn Beverly! 5 Min to Salem!
Beverly
9.0 out of 10, Wonderful, (17 reviews)
"Great location!!! Great rental, excellent host!!"
United States
Jennifer G.
The price is CA $131
CA $325 total
includes taxes & fees
Jun 28 - Jun 29
Dwtn Beverly! 5 Min to Salem!

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.8 out of 10, Exceptional, (11 reviews)
"Great place to stay close to Boston. Lots of food choices in the immediate area. The space was clean, spacious and had a great old school charm. "
United States
Ashleigh K.
The price is CA $192
CA $355 total
includes taxes & fees
Jul 14 - Jul 15
Enjoyable 2-bedroom lower level apartment in charming Lynn

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (121 reviews)
"This was. A very nice, clean room. Plenty big enough for one or two people and great location, lots of dining and by the park"
United States
Rachel
The price is CA $206
CA $236 total
includes taxes & fees
Jun 28 - Jun 29
Maverick Suites at 40 Temple St

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead Historic District
9.8 out of 10, Exceptional, (74 reviews)
"Great location, clean and comfortable, responsive host. Overall, a terrific stay. "
United States
Tiffany F.
The price is CA $160
CA $399 total
includes taxes & fees
Jun 30 - Jul 1
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
The price is CA $202
CA $518 total
includes taxes & fees
Jun 29 - Jun 30
Beautiful 1BR near Fenway Park + Kenmore!

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 CA $135
CA $309 total
includes taxes & fees
Jun 30 - Jul 1
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (289 reviews)
"Amazing location we loved it"
United States
MARLYN
The price is CA $197
CA $373 total
includes taxes & fees
Jun 29 - Jun 30
Kasa Boston at Fenway

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
10.0 out of 10, Exceptional, (1 review)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
The price is CA $156
CA $451 total
includes taxes & fees
Jun 30 - Jul 1
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (712 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
The price is CA $217
CA $413 total
includes taxes & fees
Jul 1 - Jul 2
Global Luxury Suites Downtown Boston

The Concord Hotel

The Concord Hotel
2.0 star property
South End
10.0 out of 10, Exceptional, (1 review)
"Overall had a great experience here. Took just a couple minutes texting the host to get the check in information that was to be emailed- but they sent it pretty quickly when I said it wasn't sent yet. I didn't need anything else from the host. It was clean and overall pretty nice! The stairs you take to get up to the room are pretty loud, so I woke up one time when other people got home to other rooms during my stay, but that was it! Overall good. I was there for a holiday weekend so the price...
United States
Jessica
The price is CA $235
CA $450 total
includes taxes & fees
Jun 28 - Jun 29
The Concord Hotel

Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (33 reviews)
"Good location for our trip. Quaint and safe neighborhood. Host very responsive. "
United States
Michelle S.
The price is CA $178
CA $485 total
includes taxes & fees
Jun 29 - Jun 30
Bright 2BR by Boston Waterfront
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?

Steps from the ocean minutes from Boston Beach house for rent 10% off first week: Visitors like this Winthrop vacation home rental. It is located near the beach and offers a selection of books, 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 fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winthrop?

With 6 Expedia vacation rentals, you're sure 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 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.