Vacation rentals in Winthrop

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Winthrop vacation rentals

Stay near Winthrop's top sights

Harpoon114 locals recommend
Antique Table Restaurant43 locals recommend
Belle Isle Seafood27 locals recommend
Constitution Beach26 locals recommend
Deer Island22 locals recommend
Cafe Rossetti's20 locals recommend

Other great vacation rentals in Winthrop

Top guest favorite
A serene beach scene features soft, sandy shores framed by scattered patches of grass. Gentle waves can be seen lapping at the shoreline, under a sky adorned with fluffy clouds and scattered blue areas, creating a tranquil coastal atmosphere.
Home in Ipswich
5 out of 5 average rating, 22 reviews

Capeview Cottage

GillianRating, 5 stars5 months ago
This place had the most amazing view.
Superhost
The entrance to the bungalow features a welcoming wooden door with a decorative glass panel. Soft lighting illuminates the path and entryway, surrounded by well-maintained plants. Stone steps lead up to the door, creating a charming approach to the home.
Home in Beverly
4.86 out of 5 average rating, 178 reviews

Beverly Beach House- Upper Deck

RachelRating, 5 stars4 months ago
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!
Guest favorite
Home in Ipswich
4.89 out of 5 average rating, 100 reviews

Hillside Ocean View 2BR with Private Beach Access

TaniaRating, 5 stars2 weeks ago
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.
Top guest favorite
A fire pit is surrounded by colorful adirondack chairs in a grassy area, with bright yellow flowers adding a pop of color. The view in the background includes a landscape of greenery leading to the water, suggesting a peaceful outdoor space for gatherings.
Home in Ipswich
4.98 out of 5 average rating, 194 reviews

Stagehill Beach House

PaulaRating, 5 stars6 months ago
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!
Top guest favorite
The kitchen features modern white cabinetry and a marble countertop. A stainless steel gas range and exhaust hood are prominently displayed. Natural light from a window illuminates a nearby sink, which is accompanied by a potted orchid and overlooks a serene view of the meadow.
Apartment in Brighton
4.99 out of 5 average rating, 79 reviews

New 3 bedroom, 2 bath unit, meadow view!

FionaRating, 5 stars2 weeks ago
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.
Guest favorite
A serene park scene is shown, with a sandy area leading to a calm body of water. People can be seen enjoying various activities under a partly cloudy sky, framed by lush greenery and large trees. A sign for Arlington Recreation is prominently displayed.
Guest suite in Arlington
4.85 out of 5 average rating, 82 reviews

★Modern Studio-Private Entrance,Washer+Dryer★

BrianRating, 5 stars4 months ago
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!
Top guest favorite
A full moon casts a golden glow over the water, illuminating the surface with shimmering reflections. In the background, two large houses with red roofs are visible, set against a twilight sky.
Apartment in Swampscott
4.98 out of 5 average rating, 40 reviews

Ocean View Apartment 2nd Floor

SherylRating, 5 stars5 months ago
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.
Superhost
Apartment in Cambridge
4.83 out of 5 average rating, 18 reviews

Elegant 3-Bed Oasis in Cambridge Near Harvard/MIT

JesseRating, 5 stars4 months ago
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.

Destinations to explore

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