196+ Private Villas and Holiday Rentals in Winthrop |
  1. USA
  2. Massachusetts
  3. Boston
  4. Winthrop

Winthrop Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Winthrop

Discover more than 196 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 710.88 ft², with nightly prices averaging ZA R4,523.

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.

Show more
Show less

Top Accommodation Types in Winthrop

Type Count
Holiday Apartments 123
Vacation Homes 26
Villas 2

Use these Quick Filters to Find a Holiday Rental in Winthrop

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winthrop.

Weather in Winthrop, MA

View the weather forecast for Winthrop before booking your Winthrop Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Winthrop, MA

Casai offers a large selection of top attractions around Winthrop . Research things to do on your vacation before you visit Winthrop.


Winthrop Beach
Donovan Beach
Point Shirley Beach
Fenway Park
Boston University
Harvard University
TD Garden
Boston Common
Faneuil Hall Marketplace
Boston Convention and Exhibition Center
New England Aquarium
Northeastern University
Boston Museum of Fine Arts
Copley Square
Harvard Square
Massachusetts General Hospital
Museum of Science
Hynes Convention Center
Massachusetts Institute of Technology

Other Places to Stay in Winthrop, MA


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

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 holiday rentals have private pools in Winthrop?

Discover a selection of holiday rentals with private pools near Winthrop with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Winthrop are best for families?

If you're searching for a family-friendly holiday home in Winthrop, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winthrop:

How many Casai.co.za holiday rentals are available in Winthrop?

As of 2026, Casai boasts over 196 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) 
Neighborhood Property Count
East Boston Vacation Rentals in Boston, Massachusetts 77
Harbor View - Orient Heights Vacation Rentals in Boston, Massachusetts 647

People Also Ask

There are 196 Winthrop, MA Holiday Rentals

Recently Booked Holiday Rentals in Winthrop