Winthrop vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Winthrop
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winthrop vacation rentals
Other great vacation rentals in Winthrop
Guest suite in Everett
4.91 out of 5 average rating, 218 reviewsBasement Apartment in prime location near Boston
Nov 3 – 10
Apartment in Marblehead
4.95 out of 5 average rating, 238 reviewsMid Town Marblehead 1 B/R Pvt. Wing w/Own Entrance
Mar 2 – 9
Guest suite in Medford
4.92 out of 5 average rating, 123 reviewsBeautiful 1 Bedroom, 1 Bathroom in Medford
Aug 24 – 31
Apartment in Salem
4.97 out of 5 average rating, 300 reviewsThe Salem House Too
Feb 9 – 16
Guest suite in Arlington
4.92 out of 5 average rating, 195 reviewsModern and comfortable studio apartment
Mar 29 – Apr 5
Apartment in Revere
4.96 out of 5 average rating, 159 reviewsIkram's Place Close to Boston,Subway,Airport,Beach
Jan 19 – 26
Guest suite in Norwell
4.95 out of 5 average rating, 260 reviewsPrivate suite South Shore
Sep 27 – Oct 4
Loft in Swampscott
4.99 out of 5 average rating, 252 reviewsGorgeous Oceanfront Penthouse
Mar 5 – 12
Other great vacation rentals in Winthrop
Guest suite in Melrose
4.84 out of 5 average rating, 240 reviewsGuest Suite with separate entrance
Aug 26 – Sep 2
Apartment in Revere
4.96 out of 5 average rating, 148 reviewsQuiet Neighborhood Luxury Stay
Feb 20 – 27
Apartment in Winthrop
4.93 out of 5 average rating, 15 reviewsVibrant Winthrop Apartment - Close to Ocean!
Feb 7 – 14
Home in Winthrop
4.84 out of 5 average rating, 44 reviewsCozy & Modern Entire Residential Home ❤️
Aug 9 – 16
Home in Winthrop
5.0 out of 5 average rating, 24 reviewsThe Day-Burrill-Wadsworth-La Voix House
Dec 13 – 20
Apartment in Winthrop
5.0 out of 5 average rating, 24 reviewsSea la Vie Oceanfront, private and public beach
May 21 – 28
Apartment in Winthrop
4.91 out of 5 average rating, 89 reviewsNewly Renovated Ocean View 2 Bdrm Apt
Dec 23 – 30
Apartment in Winthrop
4.86 out of 5 average rating, 64 reviewsOceanfront apartment, 15min from Boston!
Apr 26 – May 3
Quick stats about vacation rentals in Winthrop
Total rentals
150 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
12K reviews
Nightly prices starting at
$40 before taxes and fees
Frequently Asked Questions
Where should I stay in Winthrop?
Make yourself at home in Winthrop by choosing from our most frequently booked neighborhoods. We have over 2,290 vacation rentals in Orient Heights, over 150 vacation rentals in Cottage Park, and over 150 vacation rentals in Beachmont.
Are there pet-friendly vacation rentals in Winthrop?
Four-legged friends are welcome in Winthrop. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Winthrop?
Yes! Work meets play with ease at over 70 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Winthrop?
Experience the best of Winthrop with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Winthrop have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winthrop have wireless internet?
Absolutely! We offer over 70 apartment rentals with wireless internet in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Winthrop?
Winthrop has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Winthrop?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 60 homes with air conditioning, over 70 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
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