Town of Italy Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Town of Italy

Hotel Canandaigua, Tapestry Collection by Hilton

Hotel Canandaigua, Tapestry Collection by Hilton

3.5 out of 5
205 Lakeshore Drive, Canandaigua, NY
Fully refundableReserve now, pay when you stay
The price is S$249 per night from 3 Nov to 4 Nov
S$249
3 Nov - 4 Nov
includes taxes & fees
8.8/10 Excellent! (257 reviews)
"This property was gorgeous, overlooking the lake. Loved waking up to that view! Great walking trail along water and park next to property."

Reviewed on 24 Sept, 2025

Hotel Canandaigua, Tapestry Collection by Hilton
The Lake House on Canandaigua

The Lake House on Canandaigua

4.5 out of 5
770 South Main Street, Canandaigua, NY
Fully refundableReserve now, pay when you stay
The price is S$404 per night from 4 Nov to 5 Nov
S$404
4 Nov - 5 Nov
includes taxes & fees
9.2/10 Wonderful! (397 reviews)
"The Lake House has left nothing to chance! The rooms are so well appointed and the lake view balconies complete with Adirondack chairs invite you to relax. Love the open lobby, versatile library for coffee or cocktails. The restaurants are delicious and the service is impeccable. Don’t miss the charm ..."

Reviewed on 2 Oct, 2025

The Lake House on Canandaigua
Hampton Inn Penn Yan

Hampton Inn Penn Yan

2.5 out of 5
110 Mace Street, Penn Yan, NY
Fully refundableReserve now, pay when you stay
The price is S$119 per night from 2 Nov to 3 Nov
S$119
2 Nov - 3 Nov
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Lake view and fireplace was beautiful. Pools were perfect."

Reviewed on 29 Sept, 2025

Hampton Inn Penn Yan
See all 1,349 properties in Town of Italy
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.

Frequently asked questions

How much does a Town of Italy holiday package cost?
Get ready to book, because a getaway to Town of Italy starts from a tempting . When you combine your flights, hotels and more into a travel package, you'll enjoy great deals.
How do I get a cheap travel package to Town of Italy?
Crafting your own Town of Italy holiday package with Expedia is such a simple way to save. We offer access to over 550 air carriers and 1,000,000 hotels around the globe. With such a broad range to pick from, you'll have no issues creating your next dream trip.
Where should I stay in Town of Italy?
With so much to discover in Town of Italy, it'd be convenient for you to book a room in a hotel near its attractions. Conklin Gully, Clarks Gully and West River Marsh are some fascinating ones to add to your to-do list.
What are the top hotels in Town of Italy?
Book a stay at Adirondack Style Lodge - Minutes From Keuka Lake. It's one of the area's most popular hotels. Another well-known option in Town of Italy is Newly Renovated Rustic Cabin W.
How far in advance should I book my Town of Italy holiday?
Reward yourself with the biggest variety and the lowest prices by booking your adventure to Town of Italy nice and early. Air carriers typically sell tickets around 12 months prior to departure, so reserve your spot as soon as you can. That being said, Expedia is dedicated to giving you the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Town of Italy travel package include?
Select from a combination of rental cars, flights and hotels. Once you've made your booking, you can add activities and tours. Want to pick your airfare class? That's also possible. The choice is all yours when it comes to creating your ideal Town of Italy getaway.
What should I know before booking a Town of Italy travel package?
When you book your flights, hotels and car rentals together, you'll be rewarded with incredible discounts. Whether you're organising an island getaway in a villa or want to stay in a convenient hotel in the city, Expedia will make it happen for less.
Can I choose my airline with a Town of Italy Expedia holiday package?
The choice is all yours! We have access to over 550 airlines around the world, so you can design your Town of Italy escape according to your needs and budget.
If I'm not able to travel, can I cancel my Town of Italy holiday package?
If your holiday plans in Town of Italy have been upended, it's a relief to know that it is possible to amend or cancel your booking. If you made your booking less than 24 hours ago, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge fees. To learn more, check our Customer Service Portal.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.