Pound Ridge Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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Your Pound Ridge Vacation

From its highlights to its hidden gems, this city is best explored with a Pound Ridge vacation package. Look for places to stay in Downtown Stamford, which is good for history, bars and pubs and dining. Make your trip to Pound Ridge even more exciting by going sightseeing. Caramoor Center for Music and the Arts, Wolf Conservation Center and John Jay Homestead State Historic Site are among the leading attractions worth exploring. Stop daydreaming and start traveling. Explore the range of options on Expedia today and put your Pound Ridge vacation plans into gear!

Top Pound Ridge Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

Manhattan
CA $907
per person
Jan 11 - Jan 15
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
Perfect! Def recommend

Reviewed on Oct 25, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
CA $991
per person
Jan 11 - Jan 15
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The staff is incredible, and the hotel is very lovely and centrally located; everything was exactly as it appears in the photos.

Reviewed on Oct 25, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

Manhattan
Save 100% on your flight
CA $3,383
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Eurostars Wall Street

Eurostars Wall Street

Manhattan
CA $1,570
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,000 reviews)
It is definitely older, Only 1 elevator was working, The fan was not working in the bathroom. The floors in the rooms need replacing as the vinyl flooring was peeling up. The bedding and heating was fine. But definitely not worth the 732.00 per night I paid.

Reviewed on Oct 24, 2026

Nova Hotel JFK

Nova Hotel JFK

Queens
CA $1,729
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
6.8/10 (640 reviews)
Ensure they provide you with a WiFi code

Reviewed on Oct 26, 2026

Ready to book your vacation to Pound Ridge?

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Pound Ridge Hotel Deals

West Gate Inn Nyack

West Gate Inn Nyack

26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
CA $139
CA $159 total
Nov 9 - Nov 10
includes taxes & fees
7.4/10 Good! (1,497 reviews)
"Nothing. The room was dirty & the bed had bed bugs. I checked out after being there just over two hours. Management couldn’t give me a different room ( not that I would taken it given the condition of the first room) They wanted to charge me for the full 3 days. I got them to bring it down to one ..."

Reviewed on Oct 25, 2026

West Gate Inn Nyack
Tarrytown House Estate

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY
CA $222
CA $289 total
Nov 24 - Nov 25
includes taxes & fees
8.2/10 Very good! (1,388 reviews)
"Upon arrival the toilet was gross, not sure how housekeeping missed what we saw immediately. Also the shower/tub didn't drain normally. The fridge in the room was turned off when we arrived, when we turned it to medium cool it froze everything in it. Staff however was great and responsive to anything ..."

Reviewed on Oct 26, 2026

Tarrytown House Estate
J House Greenwich

J House Greenwich

1114 E. Putnam Ave Riverside CT
CA $367
CA $480 total
Nov 20 - Nov 21
includes taxes & fees
J House Greenwich
See all 1,264 properties in Pound Ridge
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.

Stay near popular Pound Ridge attractions

Pound Ridge Town Park

Pound Ridge Town Park is just one of the places to see in Pound Ridge, so why not enjoy the other things to explore during your travels? Take in the museums while you're in the area.
See properties

Pound Ridge Library

Enjoy an outing to Pound Ridge Library during your stay in Pound Ridge. Take in the museums while you're in the area.
See properties

Frequently asked questions

How much does a Pound Ridge vacation package cost?
You'll find cheap prices from CA $907 on Expedia for your Pound Ridge escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Pound Ridge costs.
What are the cheapest months to go to Pound Ridge?
To pick up cheap Pound Ridge vacation packages, plan your getaway outside of peak periods such as school holidays. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for Pound Ridge?
You can easily explore all the leading sights in Pound Ridge in a few days, including the must-see Stamford Historical Society Museum. If you want a longer Pound Ridge vacation, check out what kind of day trips and activities are available nearby.
How to find the best Pound Ridge package deals?
Begin your search for a Pound Ridge package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Pound Ridge package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pound Ridge escape underway.
Is it cheaper to book a Pound Ridge vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can personalize your Pound Ridge trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Pound Ridge?
If you're planning a spontaneous Pound Ridge vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Pound Ridge?
  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Pound Ridge.
  2. Plan your budget wisely: Besides the cost of your hotel, you should consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may arise during your trip to Pound Ridge.
  3. Decide how long to go for: Now that you know more about Pound Ridge, you can work out the right length of your break. Put together a rough plan and allocate enough time to cover everything you want to see.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Pound Ridge vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.