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

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.
The price is CA $273
CA $523 total
includes taxes & fees
Sep 1 - Sep 2
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking

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.
The price is CA $174
CA $354 total
includes taxes & fees
Aug 19 - Aug 20
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

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

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
The price is CA $344
CA $508 total
includes taxes & fees
Aug 18 - Aug 19
Beautiful 3-bedroom apartment with AC in welcoming Winthrop

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.
The price is CA $221
CA $597 total
includes taxes & fees
Sep 1 - Sep 2
2BR Historic Marblehead Home+Minutes to Beach

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.
The price is CA $238
CA $443 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown

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
The price is CA $125
CA $346 total
includes taxes & fees
Aug 18 - Aug 19
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

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
The price is CA $258
CA $325 total
includes taxes & fees
Aug 31 - Sep 1
1880 updated Victorian 1st floor, water views

8. Lovely two bedrooms in the great historic town

Lovely two bedrooms in the great historic town
Salem
9.6 out of 10, Exceptional, (88 reviews)
"Great place to stay and ver clean!"
United States
Sharon A.
The price is CA $163
CA $347 total
includes taxes & fees
Aug 24 - Aug 25
Lovely two bedrooms in the great historic town

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.
The price is CA $205
CA $489 total
includes taxes & fees
Aug 24 - Aug 25
Hocus Pocus Season is here! Don’t miss it!

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.
The price is CA $395
CA $983 total
includes taxes & fees
Aug 20 - Aug 21
Coastal Charm: Lobster Châto

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)
"This was a lovely place in the perfect location to explore Salem on foot. Very clean and comfortable with a fun vibe. "
United States
Laura B.
The price is CA $237
CA $523 total
includes taxes & fees
Aug 23 - Aug 24
1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking

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.
The price is CA $225
CA $462 total
includes taxes & fees
Sep 8 - Sep 9
Re-listed: Adorable Condo Beverly - Salem - Halloween

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, (111 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
The price is CA $347
CA $654 total
includes taxes & fees
Aug 17 - Aug 18
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

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.
The price is CA $341
CA $841 total
includes taxes & fees
Aug 30 - Aug 31
Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284

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)
"The apartment is walkable to the major sites and good restaurants. The rooms and kitchen were clean. I enjoyed my stay."
United States
Jennifer G.
The price is CA $358
CA $717 total
includes taxes & fees
Aug 20 - Aug 21
Park & Play • Walk To Bars • Sleep in Luxury

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.
The price is CA $178
CA $363 total
includes taxes & fees
Aug 24 - Aug 25
Central Salem Retreat 2bd W/ parking

17. Salem Haunted Happenings Retreat

Salem Haunted Happenings Retreat
Salem
9.6 out of 10, Exceptional, (31 reviews)
"Great place!"
United States
Jeffrey
The price is CA $188
CA $374 total
includes taxes & fees
Aug 24 - Aug 25
Salem Haunted Happenings Retreat

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
The price is CA $433
CA $989 total
includes taxes & fees
Aug 24 - Aug 25
Family-Friendly Salem Apt: Near Dtwn Sites!

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
The price is CA $282
CA $580 total
includes taxes & fees
Aug 18 - Aug 19
Cozy Salem Getaway. Historic Home Near All the Sights

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.
The price is CA $339
CA $710 total
includes taxes & fees
Aug 20 - Aug 21
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

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?

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.