Waterside Vacations from $296

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The Latest Waterside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
Price was $432, price is now $296 per person
$296
per person
Feb 26 - Mar 1
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
8.4/10 Very Good! (1,012 reviews)
Everything was good!!!

Reviewed on Dec 1, 2025

Ultra-Modern Luxe Sleek & Stunning Stay

Ultra-Modern Luxe Sleek & Stunning Stay

2 out of 5
Save 100% on your flight
Price was $1,889, price is now $1,209 per person
$1,209
per person
Jan 15 - Jan 20
found 2 days ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
2/10 (1 review)
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

2 out of 5
Southeast Yonkers
Price was $1,031, price is now $681 per person
$681
per person
Jan 1 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
No reviews
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
Ridgeway-Bullshead
Price was $790, price is now $527 per person
$527
per person
Jan 15 - Jan 20
found 2 days ago
Roundtrip non-stop flight included
Los Angeles (LAX) to White Plains (HPN)
7.8/10 Good! (674 reviews)
Stayed for 2 nights. Solid hotel. Beds were comfortable. Breakfast was standard and good. In and out self park for reasonable fee. Didn't get to use the pool or game room, so can't comment on those. Note that this hotel is a great for religious Jews - kosher restaurant, key locks on the room doors for Shabbat, Shabbat friendly lights in the room, a shul, a mikvah.

Reviewed on Nov 29, 2025

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Save 100% on your flight
Price was $527, price is now $364 per person
$364
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to White Plains (HPN)
8/10 Very Good! (1,001 reviews)
Beautiful property highly recommend if in the area goose feather is a great on site resteraunt as well

Reviewed on Dec 1, 2025

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Where to stay in Waterside

Find the best Waterside areas and neighborhoods for the activities you enjoy most. Learn more about Waterside
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Downtown Stamford

3 out of top 10 points of interest in this area
4/5(199 area reviews)

Central business district with major retail establishments, a shopping mall, and a university campus. Explore the historic district's architecture, enjoy bars and restaurants near Columbus Park, and easily access the Metro-North train station.

Find hotels in Downtown Stamford

Waterside Hotel Deals

DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

3.5 out of 5
1 First Stamford Pl Stamford CT
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $178 total per night from Dec 21 to Dec 22
$178 total
Dec 21 - Dec 22
Total with taxes and fees
7.4/10 Good! (1,024 reviews)
Very friendly staff, clean and comfortable room.

Reviewed on Nov 30, 2025

DoubleTree by Hilton Stamford
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue Stamford CT
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $95 total per night from Dec 7 to Dec 8
$95 total
Dec 7 - Dec 8
Total with taxes and fees
6.6/10 (989 reviews)
The location is great and convenient! The staff is very kind and attentive!

Reviewed on Nov 30, 2025

La Quinta Inn & Suites by Wyndham Stamford / New York City
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $148 total per night from Dec 9 to Dec 10
$148 total
Dec 9 - Dec 10
Total with taxes and fees
8.2/10 Very Good! (1,475 reviews)
Comfortable and clean. In a good location off the highway and near the bridge. Great price for location!

Reviewed on Dec 1, 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,231 properties in Waterside
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
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Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Waterside

Chelsea Piers

Take the family on an outing to Chelsea Piers during your trip to Stamford. Savor the top-notch restaurants and lively bars while in town.

Chelsea Piers

Stamford Town Center

You can find the perfect gifts to bring home at Stamford Town Center during your trip to Stamford. Check out the top-notch restaurants or lively bars in this family-friendly area.

Stamford Town Center

Stamford Center for the Arts

Enjoy a performance at Stamford Center for the Arts, a storied theater in Stamford. Check out the top-notch restaurants or lively bars in this family-friendly area.

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