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 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Winthrop vacation rentals

Interior

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 ￥34,240
￥64,416 total
includes taxes & fees
Jul 29 - Jul 30
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
Smart TV, books, stereo

Village Colonial / Harbor Views.

Village Colonial / Harbor Views.
Cohasset
9.8 out of 10, Exceptional, (57 reviews)
"Second time staying at this beautiful Cohasset destination and home. Would love to come back again. Excellent location, harbor walks, downtown walks, comfortable beds, well appointed kitchen, everything you need!"
United States
Beth G.
The price is ￥69,628
￥137,668 total
includes taxes & fees
Aug 3 - Aug 4
Village Colonial / Harbor Views.
Marina

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, (31 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 ￥33,913
￥60,571 total
includes taxes & fees
Aug 2 - Aug 3
Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Marina

♥ 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, (77 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 ￥24,093
￥53,263 total
includes taxes & fees
Aug 17 - Aug 18
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marina

Sailors Aweigh: Marblehead 3BR Retreat with Outdoor Space Near Harbor & Beaches

Sailors Aweigh: Marblehead 3BR Retreat with Outdoor Space Near Harbor & Beaches
Marblehead
9.8 out of 10, Exceptional, (21 reviews)
"This property was a great stay, very comfortable for our stay. Great location,! was very happy with our choice."
United States
Nancy S.
The price is ￥56,358
￥124,074 total
includes taxes & fees
Aug 2 - Aug 3
Sailors Aweigh: Marblehead 3BR Retreat with Outdoor Space Near Harbor & Beaches
Interior

1880 updated Victorian 1st floor, water views

1880 updated Victorian 1st floor, water views
Salem
10.0 out of 10, Exceptional, (24 reviews)
"Great location, beautiful view of the water. Comfortable and beautifully decorated accommodations. "
United States
Jeff A.
The price is ￥30,227
￥38,705 total
includes taxes & fees
Aug 5 - Aug 6
1880 updated Victorian 1st floor, water views
Beach

Lovely 1.5 bedroom in the great historic town

Lovely 1.5 bedroom in the great historic town
Salem
9.6 out of 10, Exceptional, (86 reviews)
"This was such a great place for my husband & I. Located in a cute little neighborhood & walking distance to various locations in Salem. Tina was a great host, she made check-in easy & the neighbors were so nice! Thanks for a great stay for our first time in Salem!"
United States
Megan
The price is ￥16,219
￥37,514 total
includes taxes & fees
Jul 30 - Jul 31
Lovely 1.5 bedroom in the great historic town
Smart TV

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, (16 reviews)
"Great location and ver comfortable stay."
United States
Michael C.
The price is ￥20,761
￥53,750 total
includes taxes & fees
Jul 29 - Jul 30
Hocus Pocus Season is here! Don’t miss it!
Exterior

Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
Swampscott
8.4 out of 10, Very Good, (8 reviews)
"Beautiful house & views,"
United States
Suzanne P.
The price is ￥47,306
￥116,894 total
includes taxes & fees
Aug 2 - Aug 3
Coastal Charm: Lobster Châto
Smart TV

Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!

Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
Salem
9.6 out of 10, Exceptional, (167 reviews)
"The place was very nice and clean. Centrally located short walk to everything. We had a wonderful time"
United States
Belkis L.
The price is ￥58,831
￥105,242 total
includes taxes & fees
Jul 28 - Jul 29
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
Smart TV

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Salem
9.6 out of 10, Exceptional, (159 reviews)
"The location was fantastic -- we were able to easily walk everywhere. The townhome was lovely, spacious and well equipped. We didn't have a car but assigned parking was located right next to the home. The owner was a pleasure to work with and made our trip a wonderful experience."
United States
Annette D.
The price is ￥48,985
￥93,878 total
includes taxes & fees
Jul 29 - Jul 30
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
1 bedroom, desk, iron/ironing board, WiFi (free)

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, (38 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 ￥25,961
￥60,110 total
includes taxes & fees
Aug 19 - Aug 20
1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking
1 bedroom, travel crib, WiFi (free), bed sheets

Re-listed: Adorable Condo Beverly - Salem - Halloween

Re-listed: Adorable Condo Beverly - Salem - Halloween
Beverly
10.0 out of 10, Exceptional, (22 reviews)
"Great location Lots of walking to good food and a few great vintage and thrift stores"
United States
Christine L.
The price is ￥15,946
￥41,418 total
includes taxes & fees
Jul 28 - Jul 29
Re-listed: Adorable Condo Beverly - Salem - Halloween
TV

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, (109 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 ￥40,794
￥77,225 total
includes taxes & fees
Aug 16 - Aug 17
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Smart TV

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, (79 reviews)
"The house is very nice and the layout is great. The third floor is super cool and the house is honestly a great price for what you get. "
United States
Caroline C.
The price is ￥21,724
￥75,871 total
includes taxes & fees
Jul 29 - Jul 30
Large 5BR Peaceful House near Perry Beach • Pet-Friendly w/Parking 284
Interior

Modern Downtown Salem 3 Bedroom - Park & Play

Modern Downtown Salem 3 Bedroom - Park & Play
Salem
10.0 out of 10, Exceptional, (76 reviews)
"This was a great place to stay in Salem. The property was comfortable, the host was responsive and we will definitely stay here again the next time we are in Salem. "
United States
Sherri C.
The price is ￥40,794
￥83,082 total
includes taxes & fees
Aug 17 - Aug 18
Modern Downtown Salem 3 Bedroom - Park & Play
TV

Central Salem Retreat 2bd W/ parking

Central Salem Retreat 2bd W/ parking
Salem
8.4 out of 10, Very Good, (19 reviews)
"It was very clean, a great location, and the host was super responsive and helpful!"
United States
Kristen N.
The price is ￥17,694
￥39,403 total
includes taxes & fees
Jul 30 - Jul 31
Central Salem Retreat 2bd W/ parking
Interior

Salem Haunted Happenings Retreat

Salem Haunted Happenings Retreat
Salem
9.6 out of 10, Exceptional, (29 reviews)
"Great place!"
United States
Jeffrey
The price is ￥28,015
￥51,371 total
includes taxes & fees
Aug 2 - Aug 3
Salem Haunted Happenings Retreat
3 bedrooms, desk, iron/ironing board, WiFi (free)

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, (50 reviews)
"Great overall stay!"
United States
Chris R.
The price is ￥30,227
￥72,010 total
includes taxes & fees
Jul 28 - Jul 29
Cozy three-bedroom home close to Boston w/ plenty of parking
Interior

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (17 reviews)
"Easy, clean and a comfortable stay"
United States
Justin P.
The price is ￥19,168
￥37,381 total
includes taxes & fees
Aug 25 - Aug 26
Enjoyable 2-bedroom lower level apartment in charming Lynn
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

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

8/10 Good
"Hôtel très bien situé près du métro, Fenway Park et Boston Commun! Hotel est propre et les chambres assez grande"
Erika 2-night trip
Posted 6 hours ago
Copley Square Hotel, a FOUND Hotel

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop using one of the methods below:

  • View our selection of featured holiday rentals in Winthrop
  • Use the map to find apartments and other holiday homes in the Winthrop neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winthrop while they last

Look no further and take a look at our great range of rental properties in Winthrop!

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.