Lake Peekskill Vacations from $321

Book a Hotel + Flight or Car together to unlock savings

Your Lake Peekskill Vacation

Planning your next exciting escape is a walk in the park with a Lake Peekskill vacation package. The neighborhood of Montrose, which is good for walking, makes a superb base to uncover the treasures of this vibrant city. Want to venture out and explore? Oscawana Lake, Boscobel House and Gardens and Graymoor - The Holy Mountain are three of the most popular places to visit during a trip to Lake Peekskill. Expedia will help you escape the everyday. Tailor your vacation to Lake Peekskill to suit your travel style, whatever that may be!

The Latest Lake Peekskill vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was $527, price is now $321 per person
$321
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (8,157 reviews)
Location location location! No-frills hotel right off of Times Square with large rooms (for Manhattan). Building is showing its age but doesn't feel dirty or run down. I'd call it "charming". Heating/AC unit is very noisy. Elevators can get crowded at checkout time.

Reviewed on Nov 12, 2026

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $807, price is now $422 per person
$422
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,359 reviews)
Fantastic place to stay! Room was very comfortable and a normal, large size. The complimentary espresso machine, water and mini bar items made the stay extremely welcoming! I will definitely be staying there again. Highly recommended.

Reviewed on Nov 12, 2026

The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Price was $906, price is now $539 per person
$539
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.4/10 Exceptional! (275 reviews)

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was $1,548, price is now $938 per person
$938
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was $2,876, price is now $1,771 per person
$1,771
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on Nov 6, 2026

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Lake Peekskill Hotel Deals

West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $124 total per night from Nov 15 to Nov 16
$124 total
Nov 15 - Nov 16
Total with taxes and fees
West Gate Inn Nyack
Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

3.5 out of 5
455 S Broadway Tarrytown NY
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $152 total per night from Dec 8 to Dec 9
$152 total
Dec 8 - Dec 9
Total with taxes and fees
7/10 Good! (1,003 reviews)
"The rooms and hotel were very clean and comfortable. The staff very nice and helpful. Good location. Would definitely stay here again."

Reviewed on Nov 12, 2026

Sleepy Hollow Hotel, a Dolce by Wyndham
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $125 total per night from Nov 22 to Nov 23
$125 total
Nov 22 - Nov 23
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
"We had to wait two hours and a half for our dinner in the large hall. Not even tells us why it took so long."

Reviewed on Nov 12, 2026

Overlook Lodge at Bear Mountain
See all 661 properties in Lake Peekskill
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.

Find the Best Lake Peekskill Vacation Packages

Lake Peekskill Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Top Sights
Clarence Fahnestock State Park, Manitoga The Russel Wright Design Center and Putnam History Museum

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Frequently asked questions

How much does a Lake Peekskill vacation package cost?
Offering excellent value package deals from $321 on Expedia, you'll be surprised at how little a vacation to Lake Peekskill costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Lake Peekskill?
July, November and December are the best times to look for cheap Lake Peekskill vacation packages. Traveling in less busy months means you'll typically find reduced prices on flights and accommodations.
How many days is enough for Lake Peekskill?
The ideal duration for your Lake Peekskill vacation depends on what you'd like to see. Typically, a few days to a week will give you enough time to go to all the main sights and explore some hidden gems along the way.
How to find the best Lake Peekskill package deals?
Start your search for a Lake Peekskill package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Lake Peekskill package deal straight away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Lake Peekskill escape off to a flying start.
Is it cheaper to book a Lake Peekskill vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still get the freedom to create a tailored Lake Peekskill vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Lake Peekskill?
If you're considering a spontaneous Lake Peekskill getaway, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Lake Peekskill vacation packages?
Your Lake Peekskill getaway should be an escape from your busy life, not a source of money worries. So to give you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.