Maybrook Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Maybrook Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
PUBLIC, an Ian Schrager hotel
Manhattan
Save 100% on your flight
Price was $1,673, price is now $1,046 per person
$1,046
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New York (NYC)
Book a stay at this business-friendly hotel in New York. Enjoy 2 restaurants, 6 bars/lounges, and a nightclub. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Outsite Chelsea
Manhattan
Save 100% on your flight
Price was $2,040, price is now $1,225 per person
$1,225
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New York (NYC)
Stay at this guesthouse in New York. Enjoy free WiFi, a rooftop terrace, and laundry facilities. Popular attractions Madison Square Garden and Bryant Park are located nearby.
Eurostars Wall Street
Manhattan
Save 100% on your flight
Price was $2,145, price is now $1,323 per person
$1,323
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New York (NYC)
Book a stay at this boutique hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Wall Street and Brooklyn Bridge are located nearby.
The Iroquois New York
Manhattan
Save 100% on your flight
Price was $2,440, price is now $1,536 per person
$1,536
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New York (NYC)
Book a stay at this luxury hotel in New York. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bryant Park and Times Square are located nearby.
Hotel Edison Times Square
Manhattan
Save 100% on your flight
Price was $1,952, price is now $1,246 per person
$1,246
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New York (NYC)
Book a stay at this business-friendly hotel in New York. Enjoy 2 restaurants, room service, and a 24-hour fitness center. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Broadway and Times Square are located nearby.
Roxy Hotel New York
Manhattan
Save 100% on your flight
Price was $1,676, price is now $1,078 per person
$1,078
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Top Hotel Deals
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
35.47 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 ...
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
26.26 km from city center
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
30.31 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 ...
Hampton Inn Harriman Woodbury
60 Centre Dr Central Valley NY
20.16 km from city center
Book a stay at this business-friendly hotel in Woodbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
13.29 km from city center
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave New Windsor NY
11.98 km from city center
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
30.05 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 ...
Wildflower Farms, Auberge Collection
2702 Main St Gardiner NY
23.16 km from city center
Book a stay at this luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery ...
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
35.44 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 ...
Sleep Inn & Suites Monroe - Woodbury
1 Sleep Way Monroe NY
14.01 km from city center
Book a stay at this business-friendly hotel in Monroe. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Hampton Inn by Hilton New Paltz
4 South Putt Corners Road New Paltz NY
31.16 km from city center
Book a stay at this business-friendly hotel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
19.02 km from city center
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality Inn & Suites Fishkill South near I-84
849 Route 52 Fishkill NY
25.32 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 ...
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, Nov 27 - Mon, Dec 1
TPA
Tampa Intl.
SWF
Stewart Intl.
$696 Roundtrip, found 4 days ago
$696
Roundtrip
found 4 days ago
Thu, Nov 27 - Mon, Dec 1
TPA
Tampa Intl.
SWF
Stewart Intl.
$714 Roundtrip, found 3 days ago
$714
Roundtrip
found 3 days ago