West Side Vacation Packages for 2026

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West Side Flight + Hotel packages

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

Amsterdam Hotel

2 out of 5
Downtown Stamford
Price was $475, price is now $396 per person
$396
per person
Sep 10 - Sep 14
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stamford Town Center and Stamford Public Library - Ferguson Library are located nearby.

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Save 100% on your flight
Price was $875, price is now $641 per person
$641
per person
Sep 10 - Sep 14
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Westchester County Center and Lyndhurst Mansion are located nearby.

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
Northwest Yonkers
Price was $628, price is now $475 per person
$475
per person
Sep 10 - Sep 14
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Untermyer Gardens Conservancy and Legoland Discovery Center Westchester are located nearby.

Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
Price was $746, price is now $577 per person
$577
per person
Sep 10 - Sep 14
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly aparthotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Stamford Public Library - Ferguson Library and Stamford Center for the Arts are located nearby.

Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa

3.5 out of 5
Downtown Stamford
Price was $873, price is now $688 per person
$688
per person
Sep 10 - Sep 14
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this spa hotel in Stamford. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Stamford Town Center and Stamford Center for the Arts are located nearby.

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Price was $622, price is now $510 per person
$510
per person
Sep 10 - Sep 14
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to White Plains (HPN)
Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westchester County Center and Westchester Skating Academy are located nearby.

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Top Hotel Deals

Hampton Inn & Suites Stamford

Hampton Inn & Suites Stamford

2.5 out of 5
26 Mill River Street Stamford CT
0.89 km from West Side
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Super 8 by Wyndham Stamford/New York City Area

Super 8 by Wyndham Stamford/New York City Area

2.5 out of 5
32 Grenhart Rd Stamford CT
0.72 km from West Side
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
21.85 km from West Side
Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
25.21 km from West Side
Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful ...
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
15.28 km from West Side
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Inn at Jericho

Inn at Jericho

2 out of 5
101 Jericho Turnpike Westbury NY
30.24 km from West Side
Stay at this motel in Westbury. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
1.02 km from West Side
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff ...
East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd. East Norwich NY
23.3 km from West Side
Book a stay at this business-friendly hotel in East Norwich. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
27.92 km from West Side
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street Elmsford NY
22.68 km from West Side
Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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
0.89 km from West Side
Stay at this hotel in Stamford. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Ramada by Wyndham Bronx

Ramada by Wyndham Bronx

3 out of 5
1000 Baychester Ave Bronx NY
29.91 km from West Side
Book a stay at this business-friendly hotel in Bronx. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester

2 out of 5
560 Saw Mill River Rd Ardsley NY
25.22 km from West Side
Book a stay at this business-friendly hotel in Ardsley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

2.5 out of 5
160 Corporate Blvd Yonkers NY
28.31 km from West Side
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
Viana Hotel and Spa, Trademark Collection by Wyndham

Viana Hotel and Spa, Trademark Collection by Wyndham

4 out of 5
3998 Brush Hollow Rd Westbury NY
30.58 km from West Side
Book a stay at this luxury hotel in Westbury. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Aug 13 - Wed, Sep 2
MCO
Orlando Intl.
LGA
LaGuardia
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Aug 13 from Orlando Intl. to LaGuardia, returning Wed, Sep 2, priced at $102 found 2 hours ago
Breeze Airways
Thu, Aug 13 - Tue, Aug 18
MCO
Orlando Intl.
HPN
Westchester County
$171 Roundtrip, found 4 days ago
$171
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Aug 13 from Orlando Intl. to Westchester County, returning Tue, Aug 18, priced at $171 found 4 days ago
American Airlines
Sat, Jan 30 - Wed, Feb 3
MCO
Orlando Intl.
LGA
LaGuardia
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Jan 30 from Orlando Intl. to LaGuardia, returning Wed, Feb 3, priced at $177 found 5 days ago
JetBlue Airways
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
LGA
LaGuardia
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Aug 12 from Orlando Intl. to LaGuardia, returning Wed, Sep 2, priced at $177 found 2 hours ago
Delta
Tue, Sep 1 - Sat, Sep 5
FLL
Fort Lauderdale - Hollywood Intl.
LGA
LaGuardia
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Sep 1 from Fort Lauderdale - Hollywood Intl. to LaGuardia, returning Sat, Sep 5, priced at $177 found 6 days ago