Smallwood Holiday Packages

Save when you book Smallwood package deals

Choose two or more items and save on your trip:

Top Smallwood holiday packages

Price found within the past 48 hours. Click for updated prices.
Grand Legacy At the Park
Tropicana Inn and Suites
Hotel Riu Plaza New York Times Square
Hard Rock Hotel New York
The Shelburne Sonesta New York

Book your Smallwood holiday

Wotif can help you save a little cash!

Our amazing package deals combine your hotels and flights to make life easier.

With the extra spending money you can see way more in Smallwood.

Act fast and save as much as $245. And keep in mind, we can connect you with more than 550 airlines and 665,000 worldwide properties — your ideal holiday is just a few clicks away.

Don't waste your precious time scanning the internet when you ought to be heading to the airport. We've got some of the leading prices anywhere online.

Car Hire in Smallwood

If you're hitting the tarmac at Sullivan County International Airport, you'll need to venture further out to hire some wheels. Your closest option is Enterprise (7 Forestburg Road (Rt. 42)), which is a short drive from the airport.

Holidays to Smallwood

Before you wave goodbye to the cat and jump in that taxi to the airport, it's not a bad idea to know a thing or two about where you're off to. Keep reading for some helpful deets about Smallwood.

So, how do you reach this unique neighbourhood from central Monticello? Easy. Journey west for 11 kilometres.

Around 7 000 people call Monticello home. Whether you're thinking of spending the whole time in Smallwood or you're wanting to venture further out, you'll most definitely rub shoulders with some interesting new people.

Top Smallwood hotels

Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

Monticello NY
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!: Pet-friendly cottage with free WiFi and 1 hot tub. Located near skiing.
We enjoyed our stay and the hot tub was great! The host was responsive and addressed issues quickly, but upon arrival the deck and the steps/pathway leading to the door were not shoveled and very icy which made going in and out bit difficult but overall a good stay. Would recommend!

Reviewed on 8 Mar 2026

Opens in a new windowCharming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
Cozy Bethel Cabin Retreat with Private Hot Tub

Cozy Bethel Cabin Retreat with Private Hot Tub

Smallwood NY
Cozy Bethel Cabin Retreat with Private Hot Tub : Pet-friendly cabin with 1 hot tub and WiFi.
It was great! Perfect size for a couple, super cozy, responsive host

Reviewed on 15 Feb 2026

Opens in a new windowCozy Bethel Cabin Retreat with Private Hot Tub
Chic Treehouse Cabin with Pedal Boat, Hot Tub, BBQ, Fire Pit, SUPs, & Lake Access

Chic Treehouse Cabin with Pedal Boat, Hot Tub, BBQ, Fire Pit, SUPs, & Lake Access

Smallwood NY
Chic Treehouse Cabin with Pedal Boat, Hot Tub, BBQ, Fire Pit, SUPs, & Lake Access: Pet-friendly cabin with free WiFi and 1 hot tub. Located on a lake.
Cute cabin

Reviewed on 30 Oct 2025

Opens in a new windowChic Treehouse Cabin with Pedal Boat, Hot Tub, BBQ, Fire Pit, SUPs, & Lake Access
Don't see what you're looking for?
See all available properties in Smallwood
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.