Chester Holiday Rentals
![Stunning Artisan Waterfall Escape [Walk to Downtown]](https://imgservice.casai.com/640x417/stunning-artisan-waterf-us-chester-ha-3211062918-0.jpg)
About Casai's Private Villas and Holiday Rentals in Chester
Discover more than 59 vacation rentals available in Chester. 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 Chester.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chester, 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 Chester. On average, places to stay near Chester offer 1114.5 ft², with nightly prices averaging US $468.
With Casai, finding and comparing holiday rentals in Chester is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Chester
| Type | Count |
|---|---|
| Vacation Homes | 27 |
| Holiday Apartments | 14 |
| Cottages | 10 |
Use these Quick Filters to Find a Holiday Rental in Chester
★ 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 Chester.
Weather in Chester, CT
View the weather forecast for Chester before booking your Chester Vacation Rentals to confirm your best time to go.
Top Attractions Around Chester, CT
Casai offers a large selection of top attractions around Chester . Research things to do on your vacation before you visit Chester.
Other Places to Stay in Chester, CT
Frequently Asked Questions About Chester?
What are the top holiday rentals in Chester?
With numerous options available in Chester, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chester:
- Autumn and Winter at the Haddam House
- COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
- Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino
- Stunning Artisan Waterfall Escape [Walk to Downtown]
- Charming Chester Retreat- Near Village Center
- Daniel Boone meets Mid Century Modern Retreatn
- Updated cottage "Beriozka" on Cedar Lake
- Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.
- Quiet Killingworth Rental w/Deck & Grill!
- Life on the Farm
Which holiday homes in Chester are best for families?
If you're searching for a family-friendly holiday home in Chester, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chester:
- Equestrian Living: It's a lifestyle "Living on the Farm" Not your ordinary Stay!
- Walk To Goodspeed Opera House from this quaint 2 BDRM APT
- Carriage House Studio Apartment
How many Casai.com holiday rentals are available in Chester?
As of 2026, Casai boasts over 59 properties listed in the Chester area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chester.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Deep River Center Vacation Rentals in Old Saybrook, Connecticut | 63 |
| Chester Center Vacation Rentals in Old Saybrook, Connecticut | 59 |
