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

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.
$405 nightly
The price is $452
Jul 13 - Jul 14
Total with taxes and fees
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Beautiful 3-bedroom apartment with AC in welcoming Winthrop

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
$340 nightly
The price is $380
Jul 13 - Jul 14
Total with taxes and fees
Beautiful 3-bedroom apartment with AC in welcoming Winthrop

"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail

"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
Boston
10.0 out of 10, Exceptional, (124 reviews)
"Overall our stay was good!"
United States
Yan B.
$629 nightly
The price is $723
Jul 23 - Jul 24
Total with taxes and fees
"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail

Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown

Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (80 reviews)
"Overall very goodexperience..great neighborhood,views,very responsive owner..overall very good stay"
United States
jeff s.
$471 nightly
The price is $541
Jul 5 - Jul 6
Total with taxes and fees
Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown

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, (247 reviews)
"Loved this experience!!! Would book this again! So convenient to see Boston! "
United States
Ellen Z.
$474 nightly
The price is $545
Jul 5 - Jul 6
Total with taxes and fees
Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard

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
$322 nightly
The price is $370
Jul 19 - Jul 20
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston

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
$270 nightly
The price is $310
Jul 3 - Jul 4
Total with taxes and fees
The Chester Hotel

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.
$208 nightly
The price is $228
Jul 6 - Jul 7
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn

Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
West Cambridge
8.4 out of 10, Very Good, (37 reviews)
"Clean apartment. Close to Harvard Square. Stairs not user-friendly."
United States
Jeffrey
$275 nightly
The price is $315
Jul 6 - Jul 7
Total with taxes and fees
Great Apartment on River/ Harvard Square two blocks

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,224 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
$170 nightly
The price is $190
Jul 5 - Jul 6
Total with taxes and fees
Crescent Suites 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.
$299 nightly
The price is $344
Jul 6 - Jul 7
Total with taxes and fees
Bright 2BR by Boston Waterfront

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very Good, (46 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
$271 nightly
The price is $310
Jul 5 - Jul 6
Total with taxes and fees
On River/Harvard Sq. two blocks

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.
$474 nightly
The price is $529
Jul 6 - Jul 7
Total with taxes and fees
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

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

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.4 out of 10, Exceptional, (23 reviews)
"Beds were comfortable, location was convenient for our needs, thankful for the shoveling and clearing of snow in the morning! "
United States
Stephanie G.
$181 nightly
The price is $202
Jul 5 - Jul 6
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in superb Canton

Dwtn Beverly! 5 Min to Salem!

Dwtn Beverly! 5 Min to Salem!
Beverly
9.0 out of 10, Wonderful, (18 reviews)
"Great location!!! Great rental, excellent host!!"
United States
Jennifer G.
$253 nightly
The price is $269
Jul 5 - Jul 6
Total with taxes and fees
Dwtn Beverly! 5 Min to Salem!

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (157 reviews)
"Great location!"
United States
Kevin
$113 nightly
The price is $130
Jul 5 - Jul 6
Total with taxes and fees
Maverick Suites at 400 Columbus Ave

Sunny Dog Friendly Union Sq 1brm

Sunny Dog Friendly Union Sq 1brm
Spring Hill
9.6 out of 10, Exceptional, (26 reviews)
"Welcoming and clean"
United States
Jacob W.
$333 nightly
The price is $372
Jul 3 - Jul 4
Total with taxes and fees
Sunny Dog Friendly Union Sq 1brm

Stunning South End/Back Bay Penthouse!

Stunning South End/Back Bay Penthouse!
South End
10.0 out of 10, Exceptional, (107 reviews)
"Great stay for several days of college touring!! Had everything we could possibly need. Hosts were very quick to respond to any questions or concerns! "
United States
Anonymous traveler
$1,868 nightly
The price is $2,147
Jul 4 - Jul 5
Total with taxes and fees
Stunning South End/Back Bay Penthouse!

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (6 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
$248 nightly
The price is $285
Jul 5 - Jul 6
Total with taxes and fees
Symple Live

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (715 reviews)
"Clean room, great staff and fantastic location for a reasonable price."
United States
April
$280 nightly
The price is $322
Jul 5 - Jul 6
Total with taxes and fees
Global Luxury Suites Downtown Boston
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 $105 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.

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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?

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 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.