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
Rental unit in Woburn
Charming 1 BR private entrance apt commuters dream
Guest suite in Medford
Beautiful 1 Bedroom, 1 Bathroom in Medford
Rental unit in Beachmont
Stunning Oceanview-4 Train Stop Logan Airport
Guest suite in Norwell
Private suite South Shore
Rental unit in Waltham
Cozy Private Studio Unit w/ Laundry and Parking!
Home in Quincy
Artist's Haven (2)
Guest suite in Peabody
Cozy NorthShore Suite Close to SALEM, MA
Barn in Nahant
Entire Beach-Town Cottage, Barn Charm, near Boston
Other great vacation rentals in Winthrop
Loft in Swampscott
Gorgeous Oceanfront Penthouse
Rental unit in Everett
Huge 1BR w/King Bed near BOS, Salem, Water &Nature
Guest suite in Watertown
Private 1BR Pied-a-terre
Place to stay in East Boston
Lovely Private Studio near Logan Airport
Rental unit in Revere
Beachside Cozy Space-Near Boston/Airport/Train
Rental unit in Beachmont
Ikram's Place Close to Boston,Subway,Airport,Beach
Guest suite in Abington
South Shore Luxury Apartment
Rental unit in Stoneham
Entire guest suite in Stoneham
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 condo rentals in Winthrop?
Experience the best of Winthrop with our condo 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 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 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 Condo Rentals in Winthrop?
Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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