Winthrop vacation rentals
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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 Medford
4.92 out of 5 average rating, 127 reviewsBeautiful 1 Bedroom, 1 Bathroom in Medford
Nov 8 – 15
Apartment in Revere
4.87 out of 5 average rating, 263 reviewsBeachside Cozy Space-Near Boston/Airport/Train
Mar 7 – 14
Guest suite in Everett
4.91 out of 5 average rating, 221 reviewsBasement Apartment in prime location near Boston
Dec 18 – 25
Apartment in Salem
4.97 out of 5 average rating, 302 reviewsThe Salem House Too
Feb 9 – 16
Guest suite in Melrose
4.84 out of 5 average rating, 244 reviewsGuest Suite with separate entrance
Mar 30 – Apr 6
Guest suite in Norwell
4.95 out of 5 average rating, 261 reviewsPrivate suite South Shore
Oct 6 – 13
Guest suite in Marblehead
4.97 out of 5 average rating, 263 reviewsPrivate Loft Right on Atlantic Avenue
Jul 10 – 17
Loft in Swampscott
4.99 out of 5 average rating, 256 reviewsGorgeous Oceanfront Penthouse
Jun 26 – Jul 3
Other great vacation rentals in Winthrop
Guest suite in Dover
4.98 out of 5 average rating, 184 reviewsPeaceful Country Home, Dover, Ma: Private Entrance
Oct 29 – Nov 5
Guest suite in Marblehead
4.92 out of 5 average rating, 246 reviewsOcean Park Retreat
Apr 4 – 11
Apartment in Stoneham
4.88 out of 5 average rating, 146 reviewsEntire guest suite in Stoneham
Dec 3 – 10
Apartment in Waltham
4.98 out of 5 average rating, 210 reviewsCozy Private Studio Unit w/ Laundry and Parking!
Mar 21 – 28
Apartment in Somerville
4.91 out of 5 average rating, 170 reviewsSpacious, private apartment in perfect location
Sep 3 – 10
Place to stay in Boston
4.78 out of 5 average rating, 192 reviewsLovely Private Studio near Logan Airport
Oct 16 – 23
Apartment in Revere
4.95 out of 5 average rating, 154 reviewsQuiet Neighborhood Luxury Stay
Oct 1 – 8
Apartment in Winthrop
4.95 out of 5 average rating, 19 reviewsVibrant Winthrop Apartment - Close to Ocean!
Apr 12 – 19
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 150 vacation rentals in Cottage Park, over 150 vacation rentals in Beachmont, and over 2,290 vacation rentals in Orient Heights.
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 apartment rentals in Winthrop?
Experience the best of Winthrop with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Winthrop have air conditioning?
Absolutely! We offer over 60 apartment rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winthrop have wireless internet?
Absolutely! We offer over 40 house rentals with wireless internet in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winthrop?
Winthrop has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Winthrop?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 40 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
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