99+ Private Villas and Holiday Rentals in Simsbury |
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Simsbury Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Simsbury

Discover more than 99 vacation rentals available in Simsbury. 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 Simsbury.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Simsbury, 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 Simsbury. On average, places to stay near Simsbury offer 1194.88 ft², with nightly prices averaging ZA R6,839.

With Casai, finding and comparing holiday rentals in Simsbury 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 Simsbury

Type Count
Vacation Homes 57
Holiday Apartments 27
Cottages 1
Villas 1

Use these Quick Filters to Find a Holiday Rental in Simsbury

★ 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 Simsbury.

Weather in Simsbury, CT

View the weather forecast for Simsbury before booking your Simsbury 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 Simsbury, CT

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


Rosedale Farms & Vineyards
Performing Arts Center at Simsbury Meadows
Phelps Tavern Museum
Talcott Mountain State Park
XL Center
Six Flags New England
Xfinity Theatre
University of Hartford
Naismith Memorial Basketball Hall of Fame
Connecticut Convention Center
MassMutual Center
Trinity College
Eastern States Exposition
MGM Springfield
Lake Compounce
Big E
Springfield Armory
Holyoke Mall
Connecticut Science Center

Other Places to Stay in Simsbury, CT


Simsbury Center 93 Properties
Phelps Tavern Museum 91 Properties
Performing Arts Center at Simsbury Meadows 90 Properties
Talcott Mountain State Park 47 Properties
Rosedale Farms & Vineyards 28 Properties

Frequently Asked Questions About Simsbury?

What are the top holiday rentals in Simsbury?

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

How many holiday rentals have private pools in Simsbury?

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

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

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

As of 2026, Casai boasts over 99 properties listed in the Simsbury area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Simsbury.

Nearby Neighborhood (1) 
Neighborhood Property Count
Simsbury Center Vacation Rentals in Hartford, Connecticut 93

People Also Ask

There are 99 Simsbury, CT Holiday Rentals

Recently Booked Holiday Rentals in Simsbury