Winthrop Holiday Rentals

We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.

Destination
Dates
Guests
Search
  • Up-front pricing
  • No markup
  • Trusted partners

Compare Holiday Rentals, Villas & Resorts in Winthrop

261 villas and rentals
Sort by
See More Properties

Luxury Holiday Rentals in Winthrop

Over 252+ Luxury Holiday Rentals in or Near Winthrop
See More Properties

Top-Rated Holiday Rentals with a Pool in Winthrop

Over 39+ The Best Private Villas and Holiday Rentals in Winthrop with a Pool
See More Properties

Pet-Friendly Holiday Rentals in Winthrop

Over 84+ Pet-Friendly Holiday Rentals in or Near Winthrop
See More Properties

Large Holiday Rentals and Private Villas in Winthrop

Over 9+ Large Holiday Rentals and Private Villas in or Near Winthrop
See More Properties

Wheelchair Accessible Holiday Homes in Winthrop

Over 50+ Wheelchair Accessible Holiday Homes in or Near Winthrop
See More Properties

Winthrop Private Villas and Holiday Homes Under $200

Over 75+ Winthrop Private Villas and Holiday Homes Under $200
See More Properties

Instantly Bookable Holiday Homes in Winthrop

Over 125+ Instantly Bookable Holiday Homes in or Near Winthrop
See More Properties

Book a Last Minute Place to Stay in Winthrop

About Casai's Private Villas and Holiday Rentals in Winthrop

Discover more than 261 vacation rentals available in Winthrop. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winthrop.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winthrop, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winthrop. On average, places to stay near Winthrop offer 564.83 ft², with nightly prices averaging £222.

With Casai, finding and comparing holiday rentals in Winthrop is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Other Places to Stay in Winthrop, MA


Donovan Beach 367 Properties
Winthrop Beach 131 Properties
Point Shirley Beach 92 Properties

There are 261 Winthrop, MA Holiday Rentals

Recently Booked Holiday Rentals in Winthrop

Frequently Asked Questions About Winthrop?

What are the top holiday rentals in Winthrop?

With numerous options available in Winthrop, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winthrop:

How many Casai.uk holiday rentals are available in Winthrop?

As of 2026, Casai boasts over 261 properties listed in the Winthrop area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winthrop.

Nearby Neighborhood (2)

NeighborhoodProperty Count
East Boston Vacation Rentals in Boston, Massachusetts 74
Harbor View - Orient Heights Vacation Rentals in Boston, Massachusetts 774