20+ Bedroom Vacation Rentals Near New York City: Your Complete Guide

Finding a vacation rental that sleeps 20, 30, 40 or 50 people near New York City is harder than it sounds. Most rentals are built for a family, not a reunion of forty. And a listing that says it sleeps 20 can mean pull-out sofas making up the difference. This guide is about cutting through that.

What to ask before you book a large group rental

A rental for a big group is a different thing from a typical vacation home. Before you commit, get clear answers to these:

• How many real beds are there? Ask for a list by bedroom, and whether sofa beds or cots are being counted.
• How many bathrooms, and who shares which? For a big group this decides how the mornings go.
• What is yours alone, and what is shared? The building, the pool, the grounds: ask about each.
• What are the rules on noise and music? Find out before you plan the party, not after.
• Can you bring in a caterer or a bartender? Some places allow any vendor, some have a list, some allow none.
• Can everyone eat at once? A dining room that seats the whole group changes the weekend.

The challenge with most large group rentals

Rentals that sleep 30 to 50 people in real beds, in real bedrooms, are hard to find, especially within a couple of hours of New York City. The other challenge is everything beyond the beds. A building that sleeps 40 needs more than a kitchen and a living room: it needs somewhere for the group to be together, and enough to do on a rainy afternoon.

Hilltop Castle World: up to 39 bedrooms near NYC

Hilltop Castle World is four separate buildings on one private 130-acre hill in Beach Lake, Pennsylvania, in the Pocono Mountains, two hours from New York City and Philadelphia. The figures below count real beds only; optional cots are listed separately.

• The Lodge: 3 bedrooms, 3 beds, 3 bathrooms, sleeps 6, plus 2 optional cots. Ping pong and an arcade basketball hoop.
• The Farmhouse: 7 bedrooms, 9 beds, 4 bathrooms, sleeps 16. A heated indoor pool open all year, a sauna and a billiard table.
• The Mansion: 11 bedrooms, 15 beds, 8 bathrooms, sleeps 26, plus 10 optional cots. An outdoor pool, an indoor hot tub room, a sauna, a 38-seat theater and a 36-seat conference room.
• The Castle: 18 bedrooms, 26 beds, 26 bathrooms, sleeps 44, with a private bathroom in every bedroom. Three outdoor pools, two bowling alleys, a 72-seat theater, a full-size indoor basketball court, a 60-seat conference room and the Legend of the Lost Kingdom, a treasure hunt through twelve hidden rooms that comes with the stay.

The four can be rented in any combination:

• The Castle and the Farmhouse: 25 bedrooms, sleeps 60.
• The Castle and the Mansion: 29 bedrooms, sleeps 70.
• All four: 39 bedrooms, 53 beds and 41 bathrooms, sleeping 92.

Each building’s page has a planner: select more than one building and it shows what the combination sleeps and what comes with it.

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How to think about combining buildings

When your group is big enough to need more than one building, what you want is buildings close enough that the group still feels like one group. At Hilltop the walks are short: the Lodge to the Mansion is about 60 seconds, the Castle to the Lodge about 60 seconds, and the Farmhouse to the Castle or the Mansion about two minutes.

Each building is a separate rental. The one you book is yours alone, with its own pools, rooms and amenities, and the grounds around it. Other groups may be staying in the buildings you have not booked, and the rest of the hill and its trails are shared with them. Take all four, and the whole hill is yours.

A few combinations come up again and again:

• A company off-site often takes the Castle and adds the Mansion for its second conference room and theater, so two sessions can run side by side.
• A family reunion in winter might add the Farmhouse for the indoor pool.
• A group a few over its bedding takes the Lodge for the rest, and nobody sleeps on a sofa.

The answers at Hilltop

To the questions above:

• Beds: each building’s tour shows every bed, bedroom by bedroom, on the floor plan, and the plans print. The optional cots are counted separately.
• Bathrooms: at the Castle every bedroom has its own. At the Mansion and the Farmhouse some bedrooms share, and the Mansion tour and Farmhouse tour show which.
• Music: indoors at a reasonable volume, no outdoor music and no DJ equipment. The hill has neighbors.
• Vendors: the caterer, bartender, games host, magician and others on our services page come to whichever building you are in, and you book them directly.
• Dining: the Castle seats 48, the Mansion 32, the Farmhouse 16 and the Lodge 8.

When to book

Large group stays need more planning than most, so start with dates. The booking calendar shows what is open and what it costs for your dates. Minimum stays vary by building and season: at the Castle, for example, it is two nights at weekends outside summer, and from June to Labor Day four nights at weekends and three midweek.

Check your dates, or tell the team the size of your group on the contact page and they will suggest the building or buildings that fit. For more planning help, see how to plan a family reunion in the Poconos for 20 to 100 guests.