109+ Private Villas and Holiday Rentals in Surprise |
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Surprise Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Surprise

Discover more than 109 vacation rentals available in Surprise. 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 Surprise.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Surprise, 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 Surprise. On average, places to stay near Surprise offer 1082.05 ft², with nightly prices averaging US $451.

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

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Top Accommodation Types in Surprise

Type Count
Vacation Homes 77
Holiday Apartments 7
Cottages 3
Villas 1

Use these Quick Filters to Find a Holiday Rental in Surprise

★ 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 Surprise.

Weather in Surprise, NY

View the weather forecast for Surprise before booking your Surprise 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 Surprise, NY

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


Hunter Mountain
Windham Mountain Resort
Kaaterskill Falls
Olana State Historic Site
Windham Vineyards and Winery
Windham Country Club
Zoom Flume
Hudson Opera House
Van Alen House
HITS-on-the-Hudson
Thacher State Park
Bailiwick Ranch and Discovery Zoo
Hudson Area Library
Dutchman’s Landing
Max and Lillian Katzman Theater
Art Omi International Arts Center - Fields Sculpture Park
North-South Lake Campground & Day Use Area
Indian Head Mountain
Kinderhook Cemetery
Martin Van Buren National Historic Site

Frequently Asked Questions About Surprise?

What are the top holiday rentals in Surprise?

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

How many holiday rentals have private pools in Surprise?

Discover a selection of holiday rentals with private pools near Surprise 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 Surprise are best for families?

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

How many Casai.com holiday rentals are available in Surprise?

As of 2025, Casai boasts over 109 properties listed in the Surprise area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Surprise.


People Also Ask

There are 109 Surprise, NY Holiday Rentals

Recently Booked Holiday Rentals in Surprise