Frequently Asked Questions

What is Holiday Hill? 

Holiday Hill is a 156-acre, private resort located on the Cheshire/Prospect town line in central Connecticut. We are a family owned business since 1954!

Is Holiday Hill open to the public?

No, each day is reserved well in advance by either one very large group for exclusive-use, or by several smaller groups for shared-use.

What types of events do you host at Holiday Hill?

We host company picnics, union outings, school trips, family reunions, church picnics and any other group event with at least 50 adult guests

How many people can Holiday Hill accommodate? 

Holiday Hill can accommodate up to 5,000 guests per day.

What are your days and hours of operation?

Holiday Hill hosts groups daily from May 1st until October 1st. Hours of operation are usually any 4 to 8 hours between 8:00 am and 11:00 pm depending on the client's needs. Saturday and Sunday events are typically from 10 am to 6 pm.

What does the price include?

Your price will include all food, entertainment and facilities that are part of your particular outing package

What is NOT included in the price?Sometimes there are optional features available that are not part of the package price, for instance, horseback riding and alcohol service.

Does Holiday Hill provide transportation for groups?

No, each group must arrange for their own form of transportation.

Can I visit Holiday Hill to see if it will serve the needs of my group?

Yes, of course. Contact our manager, Jerry Grella and he will be happy connect with you and set up a tour of our facility. Jerry can be reached at (203)272-5358 or

How do I make a reservation for my group?

Please fill out the "contact us form" on the website or by phone/email to make your reservation. An outing contract will be emailed to you along with next steps to making your event memorable.

What forms of payment are accepted?

From private groups such as family reunions and churches, we accept payment by bank check, money order, MasterCard or VISA. From companies we accept company checks, bank checks, MasterCard or VISA. From schools we accept school checks, bank checks, money orders, MasterCard or VISA.

Are pets allowed at Holiday Hill?

Pets are not allowed on the premises due to food safety regulations - with the exception of service dogs for the disabled.

What if it rains the day of the event?We host events in all kinds of weather. If rain is forecast on the day of your event,  do not worry, our staff is experienced in "switching gears" for those inevitable days and will work even harder than usual to provide your group with a great day of fun.

What do guests need to bring with them?

Guests should bring bathing suits, towels and a smile. Holiday Hill provides all sporting equipment. Guests should also dress appropriately for the weather and bring sunscreen if desired. And of course, a fun attitude will ensure a terrific experience.

Are guests allowed to bring alcohol into the resort?

No. Under the terms of our Connecticut State liquor license, the customer may not bring their own alcohol.

My group is tax exempt. Do we have to pay the Connecticut Sales Tax?

The CT Dept. of Revenue Services has established special rules with regard to purchases of "meals". We are happy to supply your group with the specific information needed to complete the exemption process. If your organization is based in Connecticut, you must provide proof of either CT sales tax exemption status (with an "E" permit), or Federal tax exemption status with a US Treasury Letter showing 501c3 exemption. If your organization is based outside of Connecticut, then you must provide proof of Federal exemption status with a US Treasury Letter showing 501c3 exemption. Connecticut will not recognize any New York, Massachussets or other out-of-state exemption permits, but will honor Federal tax exempt status. Once exemption status has been proven, there is a particular CT exemption form that must be completed. We can assist you with the proper form.

Do not hesitate to call the office with any questions, (203)272-5358