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

Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winthrop vacation rentals

Interior

1. Casa de Los Clarey • Boston • Logan • Beaches • Free Parking

Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
Winthrop
10.0 out of 10, Exceptional, (57 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
$337 nightly
The price is $376
Sep 1 - Sep 2
Total with taxes and fees
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
Interior

2. Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Winthrop
9.8 out of 10, Exceptional, (12 reviews)
"Great location and wonderful hosts! Would definitely recommend to anyone staying in the Boston area. "
United States
Kristie P.
$240 nightly
The price is $268
Aug 18 - Aug 19
Total with taxes and fees
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Interior

3. Beautiful 3-bedroom apartment with AC in welcoming Winthrop

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
$328 nightly
The price is $366
Aug 18 - Aug 19
Total with taxes and fees
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Coffee/tea maker, fridge, microwave, oven

4. 2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (25 reviews)
"Enjoyed our stay. "
United States
Mary D.
$370 nightly
The price is $413
Sep 1 - Sep 2
Total with taxes and fees
2BR Historic Marblehead Home+Minutes to Beach
Marina

5. Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown

Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Marblehead
10.0 out of 10, Exceptional, (35 reviews)
"Adorable studio, has everything you could need! The host was super responsive and welcoming. Would absolutely stay there again. "
United States
Alisha J.
$289 nightly
The price is $323
Aug 25 - Aug 26
Total with taxes and fees
Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Marina

6. ♥ 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, (78 reviews)
"We had a wonderful stay! The studio was clean, cozy, and located in a beautiful historic house. It was also conveniently close to downtown, which made it easy to explore the area. The check-in instructions were clear and easy to follow. Communication with the host was excellent—they responded quickly and were very helpful whenever we had a question. Overall, we really enjoyed our stay and would definitely recommend this place!"
Canada
Camille
$217 nightly
The price is $242
Aug 18 - Aug 19
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Interior

7. 1880 updated Victorian 1st floor, water views

1880 updated Victorian 1st floor, water views
Salem
10.0 out of 10, Exceptional, (29 reviews)
"We had a great stay! Place was beautiful and nearby to main attractions of Salem."
United States
Gregory
$206 nightly
The price is $230
Aug 31 - Sep 1
Total with taxes and fees
1880 updated Victorian 1st floor, water views
Beach

8. Lovely two bedrooms in the great historic town

Lovely two bedrooms in the great historic town
Salem
9.6 out of 10, Exceptional, (89 reviews)
"Great place to stay and ver clean!"
United States
Sharon A.
$215 nightly
The price is $240
Aug 24 - Aug 25
Total with taxes and fees
Lovely two bedrooms in the great historic town
Smart TV

9. 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, (17 reviews)
"Great location and ver comfortable stay."
United States
Michael C.
$301 nightly
The price is $336
Aug 19 - Aug 20
Total with taxes and fees
Hocus Pocus Season is here! Don’t miss it!
Exterior

10. Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
Swampscott
8.6 out of 10, Excellent, (9 reviews)
"Beautiful house & views,"
United States
Suzanne P.
$552 nightly
The price is $590
Aug 20 - Aug 21
Total with taxes and fees
Coastal Charm: Lobster Châto
1 bedroom, desk, iron/ironing board, WiFi (free)

11. 1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking

1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking
Salem
10.0 out of 10, Exceptional, (39 reviews)
"Very clean and the location was super convenient to walking around Salem. Host was highly responsive and we enjoyed our trip!"
United States
Charity C.
$289 nightly
The price is $323
Aug 19 - Aug 20
Total with taxes and fees
1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking
1 bedroom, travel crib, WiFi (free), bed sheets

12. Re-listed: Adorable Condo Beverly - Salem - Halloween

Re-listed: Adorable Condo Beverly - Salem - Halloween
Beverly
10.0 out of 10, Exceptional, (23 reviews)
"Great location Lots of walking to good food and a few great vintage and thrift stores"
United States
Christine L.
$276 nightly
The price is $308
Aug 24 - Aug 25
Total with taxes and fees
Re-listed: Adorable Condo Beverly - Salem - Halloween
TV

13. Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Downtown Salem
9.6 out of 10, Exceptional, (112 reviews)
"This place was perfect. Clean, a saved parking spot, within walking distance of everything you could want in Salem as well as the train station. Will definitely be looking into this if we decide to come back"
United States
Jacob
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Smart TV

14. Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284

Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284
Quincy
9.8 out of 10, Exceptional, (80 reviews)
"Nice quiet street perfect for families and close to Boston."
United States
Alisa O.
$532 nightly
The price is $595
Aug 30 - Aug 31
Total with taxes and fees
Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284
Interior

15. Park & Play • Walk To Bars • Sleep in Luxury

Park & Play • Walk To Bars • Sleep in Luxury
Salem
10.0 out of 10, Exceptional, (81 reviews)
"Tristan was great to work with and very responsive to any questions I had before and during my stay. Highly recommend this location and host!"
United States
Amanda C.
$433 nightly
The price is $484
Aug 20 - Aug 21
Total with taxes and fees
Park & Play • Walk To Bars • Sleep in Luxury
TV

16. Central Salem Retreat 2bd W/ parking

Central Salem Retreat 2bd W/ parking
Salem
8.4 out of 10, Very Good, (21 reviews)
"It was very clean, a great location, and the host was super responsive and helpful!"
United States
Kristen N.
$245 nightly
The price is $249
Aug 24 - Aug 25
Total with taxes and fees
Central Salem Retreat 2bd W/ parking
Interior

17. Salem Haunted Happenings Retreat

Salem Haunted Happenings Retreat
Salem
9.6 out of 10, Exceptional, (31 reviews)
"Great place!"
United States
Jeffrey
$262 nightly
The price is $266
Aug 23 - Aug 24
Total with taxes and fees
Salem Haunted Happenings Retreat
TV, offices

18. Family-Friendly Salem Apt: Near Dtwn Sites!

Family-Friendly Salem Apt: Near Dtwn Sites!
Salem
10.0 out of 10, Exceptional, (40 reviews)
"House was impeccably clean and designed so beautifully. The location was a quiet little street full of lovely historic homes. The beds were so comfortable! Joe was a super nice and responsive host and helped us out when our flight got changed and our arrival time was several hours earlier than expected. We truly enjoyed our stay here."
United States
Sarah
$568 nightly
The price is $649
Aug 24 - Aug 25
Total with taxes and fees
Family-Friendly Salem Apt: Near Dtwn Sites!
Exterior

19. Cozy Salem Getaway. Historic Home Near All the Sights

Cozy Salem Getaway. Historic Home Near All the Sights
Salem
9.6 out of 10, Exceptional, (59 reviews)
"Beautiful 2 bedroom, close to everything , host was wonderful, we will be back. "
United States
Charlene
$350 nightly
The price is $391
Aug 18 - Aug 19
Total with taxes and fees
Cozy Salem Getaway. Historic Home Near All the Sights
3 bedrooms, desk, iron/ironing board, WiFi (free)

20. 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, (52 reviews)
"Great overall stay!"
United States
Chris R.
$461 nightly
The price is $515
Aug 18 - Aug 19
Total with taxes and fees
Cozy three-bedroom home close to Boston w/ plenty of 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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Great property in a fab location - loved the free daily bottled water too"
Karen 5-night trip
Posted less than an hour ago
Harborside Inn Of Boston

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 $200 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.

Explore a world of travel with Expedia

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 Donovan 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.