
Vacation rentals in Winthrop
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Top-rated vacation rentals in Winthrop
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Popular amenities for Winthrop vacation rentals
Other great vacation rentals in Winthrop

Capeview Cottage
This place had the most amazing view.

Beverly Beach House- Upper Deck
We stayed here for a week, and fell in love with it! The house has so much charm and character. We thoroughly enjoyed our stay, and want to stay there again. It was within walking distance to many places, including a beach. A definite charm in Beverly! The host was amazing! She was very responsive to our questions, and checked in a few times to see if we needed anything, which I appreciated. You are missing out if you don’t stay here!

Hillside Ocean View 2BR with Private Beach Access
We love Ipswich and are so glad to find this gem of Airbnb. Mark's communications are topnotched and he proactively checked in with us to ensure that everything is alright. The house has everything we needed and more....not just for short stays but equally suitable for longer stays too. The bed and pillows were very comfortable. The house heating system is very efficient and heats up the whole house quickly and comfortably for the few cold days we were staying there. My husband loved having a dedicated work space which had a beautiful water view. There were plenty of supplies in the kitchen, bathroom and laundry. Everything is very well thought out. It might be an older house but it's very quaint, cosy and quintessentially New England. Although we had several days of lousy weather.... we still managed to do plenty out of the few half days when the skies cleared out. Oh and thank you for the very lovely cranberry banana bread... its one of the best that we've ever eaten.

Stagehill Beach House
Loved this rental! Katie was so nice and very accommodating! This house was great! Pictures didn’t do it justice! Plenty of room and amazing views. My favorite room was the sitting room upstairs with views from every window! Lots of clean linens and super comfy beds! Check in and check out were a breeze. Easy to follow instructions on how to close up. Only complaint was on me! Wish we booked “in season” to take advantage of the beach! We will definitely be back! Thank you again, Katie! Your place and you, were top notch!

New 3 bedroom, 2 bath unit, meadow view!
Simon’s place has everything you need and more. Fridge stocked with bottled water and sodas. Chocolates, oranges and bars for snacking. Bouquet of fresh flowers in the master bedroom. We felt very welcomed into this wonderful space. It is on the second floor of a 3 level house. Three apartments total in the building. Great to have off street parking. I highly recommend.

★Modern Studio-Private Entrance,Washer+Dryer★
Had a great stay at this place (this was our second time there). Our plane to the area was much delayed but our hosts were understanding and very helpful. Everything was as advertised and the place was convenient to our activities visiting family. Will definitely stay there again!

Ocean View Apartment 2nd Floor
We have had a lot of luck with AirBnB, but Valeri's place was the best so far. Literally across the street from beach access. A great restaurant next door with several others in easy walking distance. Minutes from Salem and Marblehead. The rental was fantastic. You could and picture it as being what you would want in a seaside vacation getaway or second home. Everything was clean, stocked, and organized. Beds were comfortable, and it was just a really all around relaxing environment. Loved the decor! Valeri was very nice and gave great local recommendations. I don't check to see if she's a "super" host, but she's number one for me. Loved our weekend getaway and would absolutely book again.

Elegant 3-Bed Oasis in Cambridge Near Harvard/MIT
Beautiful property and excellent location. Extremely convenient for our family to enjoy thanksgiving with family. Excellent communicators and very flexible with our travel schedule.
Quick stats about vacation rentals in Winthrop
Total rentals
190 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
16K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
10 properties have a pool
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 2,560 vacation rentals in Orient Heights, over 190 vacation rentals in Beachmont, and over 190 vacation rentals in Cottage Park.
Are there vacation rentals with a dedicated workspace in Winthrop?
Yes! Work meets play with ease at over 80 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 $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Winthrop?
Four-legged friends are welcome in Winthrop. Choose from more than 50 vacation rentals for guests traveling with pets.
Do apartment rentals in Winthrop have air conditioning?
Absolutely! We offer over 80 apartment rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winthrop have a gym?
Absolutely! We offer over 10 apartment rentals with a gym in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winthrop have wireless internet?
Absolutely! We offer over 90 apartment rentals with wireless internet in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Are there Winthrop apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 apartment rentals with pools in Winthrop, available on Airbnb. Make a splash and soak up the sun in style!
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 air conditioning, over 10 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly house rentals in Winthrop?
Winthrop has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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- Hampton Beach
- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- North Hampton Beach
- Brown University
- New England Aquarium
- Sandwich Glass Museum
- Sagamore Beach
- Faneuil Hall Marketplace
- Freedom Trail
- Onset Beach
- Prudential Center
- Symphony Hall
- Roger Williams Park Zoo
- Boston Public Library
- Crane Beach
- Rye North Beach
- Scusset Beach
- Pinehills Golf Club
- Aaronap Cellars
- John Hancock Tower
- Boston Children's Museum
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