Holmes Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Holmes Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York
Manhattan
Save 100% on your flight
Price was $701, price is now $371 per person
$371
per person
Feb 15 - Feb 20
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
Book a stay at this business-friendly hotel in New York. Enjoy breakfast (surcharge), a health club, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Central Terminal and Bryant Park are located nearby.
INNSiDE by Meliá New York Nomad
Manhattan
Price was $1,025, price is now $445 per person
$445
per person
Feb 15 - Feb 20
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Madison Square Garden and Bryant Park are located nearby.
Margaritaville Resort Times Square
Manhattan
Save 100% on your flight
Price was $868, price is now $455 per person
$455
per person
Feb 15 - Feb 20
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
Stay at this hotel in New York. Enjoy breakfast (surcharge), a fitness center, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Times Square and Bryant Park are located nearby.
Courtyard New York Manhattan/Upper East Side
Manhattan
Price was $971, price is now $520 per person
$520
per person
Feb 15 - Feb 20
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
Book a stay at this business-friendly hotel in New York. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Central Park and 5th Avenue are located nearby.
YOTEL New York Times Square
Manhattan
Save 100% on your flight
Price was $701, price is now $377 per person
$377
per person
Feb 15 - Feb 20
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to New York (NYC)
Book a stay at this boutique hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
Millennium Hilton New York One UN Plaza
Manhattan
Save 100% on your flight
Price was $995, price is now $535 per person
$535
per person
Feb 15 - Feb 20
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Central Terminal and Bryant Park are located nearby.
Top Hotel Deals
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
27.34 km from city center
Book a stay at this golf hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
28.21 km from city center
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hotel Zero Degrees Danbury
15 Milestone Road Danbury CT
18.57 km from city center
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff ...
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
20.72 km from city center
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
35.63 km from city center
Book a stay at this business-friendly hotel in Highland. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
25.97 km from city center
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Hotel MTK Mount Kisco
1 Pat Reilly Way Mount Kisco NY
34.32 km from city center
Book a stay at this business-friendly hotel in Mount Kisco. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz Poughkeepsie NY
30.96 km from city center
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Quality Inn & Suites Fishkill South near I-84
849 Route 52 Fishkill NY
22.69 km from city center
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Danbury/Bethel
11 Stony Hill Road Bethel CT
23.68 km from city center
Book a stay at this business-friendly hotel in Bethel. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our ...
Courtyard by Marriott Poughkeepsie
2641 South Road/Route 9 Poughkeepsie NY
28.67 km from city center
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
25 OLD VINEYARD PLACE Hyde Park NY
34.06 km from city center
Book a stay at this business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Home2 Suites By Hilton Poughkeepsie
2619 South Road Poughkeepsie NY
28.64 km from city center
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Locust Grove and McCann Golf ...
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.
Mon, Feb 2 - Sat, Feb 7
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Thu, Feb 5 - Sun, Feb 8
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Thu, Feb 5 - Sun, Feb 8
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$182 Roundtrip, found 1 day ago
$182
Roundtrip
found 1 day ago
Thu, Nov 27 - Mon, Dec 1
MCO
Orlando Intl.
SWF
Stewart Intl.
$379 Roundtrip, found 3 days ago
$379
Roundtrip
found 3 days ago