Waterside Vacations from $435

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The Latest Waterside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Stamford Hotel

The Stamford Hotel

3.5 out of 5
Downtown Stamford
Save 100% on your flight
Price was $591, price is now $435 per person
$435
per person
Oct 14 - Oct 18
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
7.8/10 Good! (1,106 reviews)
Nice staff. Comfortable room. Great location.

Reviewed on Aug 26, 2025

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $2,973, price is now $1,856 per person
$1,856
per person
Oct 22 - Oct 27
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
3/10 (4 reviews)
Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $3,457, price is now $2,196 per person
$2,196
per person
Oct 22 - Oct 27
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
2/10 (1 review)
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Save 100% on your flight
Price was $581, price is now $448 per person
$448
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to White Plains (HPN)
8/10 Very Good! (1,003 reviews)
Brianne at the front desk was incrediblely helpful.

Reviewed on Aug 27, 2025

Charcoal Chalet by Avantstay A+ Design w/ Firepit

Charcoal Chalet by Avantstay A+ Design w/ Firepit

3 out of 5
Save 100% on your flight
Price was $1,176, price is now $912 per person
$912
per person
Oct 10 - Oct 13
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
No reviews

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

2 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

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
$94 nightly
The price is $108 total per night from Sep 18 to Sep 19
$108 total
Sep 18 - Sep 19
Total with taxes and fees
6.4/10 (746 reviews)
"The staff were great people, efficient, helpfull and attentive. Great attitudes. The Hotel is sparkling and safe inside."

Reviewed on Aug 22, 2025

La Quinta Inn & Suites by Wyndham Stamford / New York City
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
$149 nightly
The price is $171 total per night from Sep 14 to Sep 15
$171 total
Sep 14 - Sep 15
Total with taxes and fees
7.4/10 Good! (1,003 reviews)
"Service was very professional. The accommodations were nice. The bed was very comfortable. Wish room had small Keurig machine. Overall what a beautiful hotel. Thank you."

Reviewed on Aug 24, 2025

DoubleTree by Hilton Stamford
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $126 total per night from Sep 7 to Sep 8
$126 total
Sep 7 - Sep 8
Total with taxes and fees
Royal Regency Hotel
See all 1,163 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
Beach Vacations
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 lively bars and top-notch restaurants 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 lively bars or top-notch restaurants 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.