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.
Millennium Hotel Broadway Times Square
Manhattan
$1,127
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
Hotel St. James
Manhattan
$1,178
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
Ok
Reviewed on Sep 25, 2026
Ink 48 Hotel
Manhattan
$1,238
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Manhattan Cruise Terminal and Broadway are located nearby.
The room and property was very clean. All the staff were amazing. Would definitely recommend this hotel!
Reviewed on Sep 24, 2026
The William Hotel Midtown, New York
Manhattan
$1,725
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Bryant Park and Grand Central Terminal are located nearby.
The Lombardy Hotel
Manhattan
$1,356
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions 5th Avenue and Grand Central Terminal are located nearby.
The Ridge Hotel
Manhattan
$1,251
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a rooftop terrace, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
The pictures in expedia have nothing to do with the reality. There si no housekeeping. Is more a hostel than a hotel
Reviewed on Sep 24, 2026
Top Hotel Deals
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
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 ...
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
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 ...
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites Danbury-Bethel
80 Newtown Road Danbury CT
Book a stay at this business-friendly hotel in Danbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
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 ...
Ramada by Wyndham Newburgh/West Point
1289 Route 300 Newburgh NY
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a nightclub. Popular attractions Hamilton Fish Bridge and Resorts ...
Mirbeau Inn & Spa Beacon
11 Mirbeau Lane Beacon NY
Book a stay at this spa hotel in Beacon. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Madame Brett Park and Howland Cultural Center ...
Comfort Suites Fishkill near Interstate 84
835 Route 52 Fishkill NY
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 ...
DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz Poughkeepsie NY
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 ...
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
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 ...
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Stay at this hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Studio 6 Extended Stay Fishkill Westage Center NY
55 W Merritt Blvd Fishkill NY
Stay at this hotel in Fishkill. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Microtel Inn & Suites by Wyndham Bethel/Danbury
80 Benedict Rd Bethel CT
Book a stay at this business-friendly hotel in Bethel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
The Thayer Hotel at West Point
674 Thayer Road West Point NY
Book a stay at this business-friendly hotel in West Point. Enjoy free WiFi, room service, 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
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
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.
Thu, Dec 10 - Sun, Dec 13
MCO
Orlando Intl.
SWF
Stewart Intl.
$168
Roundtrip
found 1 day ago
Sat, Oct 31 - Sat, Nov 7
JAX
Jacksonville Intl.
HPN
Westchester County
$259
Roundtrip
found 17 hours ago
Tue, Oct 27 - Tue, Nov 3
MCO
Orlando Intl.
HPN
Westchester County
$297
Roundtrip
found 22 hours ago
Wed, Oct 28 - Wed, Nov 4
JAX
Jacksonville Intl.
HPN
Westchester County
$313
Roundtrip
found 17 hours ago
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