Pound Ridge Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was CA $942, price is now CA $600 per person
CA $600
per person
Aug 2 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,828 reviews)
The bathtub was slippery and the tap was tight. I slipped and fell when trying to fix the tap and cracked a rib. The hotel just sent a bath tub mat but offered no compensation for the medical treatment i underwent in urgebnt care. They offered to fix the tap and probably fixed it.

Reviewed on Jul 2, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,109, price is now CA $3,795 per person
CA $3,795
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Atmosphere was amazing. Layout was incredibly unique. Will definitely be returning

Reviewed on Jul 2, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,994, price is now CA $1,277 per person
CA $1,277
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,632 reviews)
From check in to check out, was very efficient, breakfast was very good, large selection! Everyone was very helpful! Will stay here again!

Reviewed on Jul 3, 2026

The Prince Kitano New York

The Prince Kitano New York

4.5 out of 5
Manhattan
Price was CA $1,777, price is now CA $1,155 per person
CA $1,155
per person
Sep 4 - Sep 7
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (2,275 reviews)
Very clean friendly staff

Reviewed on Jul 3, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,511, price is now CA $984 per person
CA $984
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
All was good

Reviewed on Jul 3, 2026

Ready to book your vacation to Pound Ridge?

 

Choose your dates

Pound Ridge Hotel Deals

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jul 12 to Jul 13
CA $180
CA $206 total
Jul 12 - Jul 13
includes taxes & fees
8/10 Very good! (1,536 reviews)
"Out dated property with 70th feel with very limited breakfast choices. Needs room renovation."

Reviewed on Jun 30, 2026

Hampton Inn White Plains/Tarrytown
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
The price is CA $236 per night from Jul 26 to Jul 27
CA $236
CA $317 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (1,326 reviews)
"They had the coffee machine in the room and different options, they had the water (unlike the other hotels) and the location was perfect"

Reviewed on Jul 2, 2026

Sonesta White Plains Downtown
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Fully refundableReserve now, pay when you stay
The price is CA $304 per night from Jul 26 to Jul 27
CA $304
CA $349 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,046 reviews)
"Loved the beautiful botanical interior. The pool and hot tub were nice after a long day. Then the bar and food were good too. The gym was perfect for morning WO. Great day spent ."

Reviewed on Jul 2, 2026

Hyatt Regency Greenwich
See all 1,254 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

Frequently asked questions

How much does a Pound Ridge vacation package cost?
You'll find cheap prices from CA $600 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.