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
Apartment in Woburn
5.0 out of 5 average rating, 103 reviewsCharming 1 BR private entrance apt commuters dream
Guest suite in Marblehead
4.97 out of 5 average rating, 267 reviewsPrivate Loft Right on Atlantic Avenue
Apartment in Revere
4.86 out of 5 average rating, 159 reviewsStunning Oceanview-4 Train Stop Logan Airport
Guest suite in Medford
4.91 out of 5 average rating, 136 reviewsBeautiful 1 Bedroom, 1 Bathroom in Medford
Apartment in Salem
4.97 out of 5 average rating, 307 reviewsThe Salem House Too
Guest suite in Norwell
4.95 out of 5 average rating, 264 reviewsPrivate suite South Shore
Home in Quincy
4.96 out of 5 average rating, 130 reviewsArtist's Haven (2)
Guest suite in Peabody
4.78 out of 5 average rating, 120 reviewsCozy place to relax after a great day!
Other great vacation rentals in Winthrop
Apartment in Revere
4.96 out of 5 average rating, 164 reviewsIkram's Place Close to Boston,Subway,Airport,Beach
Barn in Nahant
5.0 out of 5 average rating, 114 reviewsEntire Beach-Town Cottage, Barn Charm, near Boston
Apartment in Revere
4.96 out of 5 average rating, 161 reviewsQuiet Neighborhood Luxury Stay
Apartment in Everett
4.92 out of 5 average rating, 206 reviewsHuge 1BR w/King Bed near BOS, Salem, Water &Nature
Guest suite in Newton
4.98 out of 5 average rating, 570 reviewsSpacious suite with private entrance, parking spot
Guest suite in Peabody
4.95 out of 5 average rating, 562 reviewsPRIVATE, LARGE COUNTRY STYLE SUITE
Apartment in Stoneham
4.87 out of 5 average rating, 163 reviewsEntire guest suite in Stoneham
Home in Everett
4.9 out of 5 average rating, 271 reviews#7 Comfortable Spacious Home Near Boston + Parking
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 Beachmont, over 2,290 vacation rentals in Orient Heights, and over 150 vacation rentals in Cottage Park.
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 condo rentals in Winthrop have air conditioning?
Absolutely! We offer over 10 condo 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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