Search Deals onOld Greenwich Vacation Packages
Old Greenwich Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Stamford Suites
Price was $525, price is now $455 per person
$455
per person
Sep 18 - Sep 20
found 22 hours ago
Roundtrip flight included
Charleston (CHS) 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 Greenwich Avenue and Pine Hill Aprtments Dog Park are located nearby.
Easy to reach from rt 95. Fee Parking, nice rm, friendly staff, free breakfast and coffee, excellent price.
Reviewed on Jul 23, 2026
Baymont by Wyndham White Plains - Elmsford
Price was $638, price is now $513 per person
$513
per person
Sep 3 - Sep 7
found 6 hours ago
Roundtrip flight included
San Juan (SJU) 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 Captain Lawrence Brewing Company are located nearby.
Good
Reviewed on Jul 24, 2026
Delamar Southport
Price was $657, price is now $549 per person
$549
per person
Sep 18 - Sep 20
found 22 hours ago
Roundtrip flight included
Charleston (CHS) to White Plains (HPN)
Book a stay at this spa hotel in Southport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Hartford HealthCare Amphitheater and Sasco Hill Beach are located nearby.
Breakfast in the morning was a terrific addition to an already pleasant stay.
Reviewed on Jul 20, 2026
La Quinta Inn & Suites by Wyndham Danbury
Price was $623, price is now $528 per person
$528
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to White Plains (HPN)
Book a stay at this business-friendly hotel in Danbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Candlewood Lake and The Cave are located nearby.
Bed was too low. Chair leg was broken. Musty smell. Noisy air conditioner.
Reviewed on Jul 23, 2026
Hyatus Luxury Residences Stamford
Save 100% on your flight
Price was $1,300, price is now $1,102 per person
$1,102
per person
Oct 8 - Oct 13
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
Book a stay at this luxury aparthotel in Stamford. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Greenwich Avenue and Stamford Town Center are located nearby.
great location, with garage spaced ( thought that is a bit confusing to figure out where the space was located); apartment was super comfy, nice size and layout, with living room/open kitchen concept (complete with all cooking and utensils ). Large bathroom w/a nice shower. Towels were wet but we worked that part out.
great gym facilities in building and a fun basement equipped with (adult) games! rooftop was not open, even to enjoy the sunny day.. which meant the pool too was not available. I will definitely stay here agin
Reviewed on May 3, 2026
Days Inn by Wyndham Elmsford / White Plains
Price was $599, price is now $513 per person
$513
per person
Sep 3 - Sep 7
found 6 hours ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
Book a stay at this business-friendly motel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westchester County Center and Westchester Skating Academy are located nearby.
Sleepy Hollow Hotel, a Dolce by Wyndham
Price was $906, price is now $778 per person
$778
per person
Oct 15 - Oct 19
found 15 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to White Plains (HPN)
Book a stay at this spa hotel in Tarrytown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westchester County Center and Lyndhurst Mansion are located nearby.
Very clean and quiet place. Breakfast wasn’t complimentary but the pool was a good size over all bed was very comfy room really clean
Reviewed on Jul 22, 2026
Best Western Danbury/Bethel
Price was $551, price is now $477 per person
$477
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to White Plains (HPN)
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 reviews. Popular attractions Candlewood Lake and The Cave are located nearby.
Old Greenwich Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Old Greenwich Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Sep 26 - Sat, Oct 10
MCO
Orlando Intl.
LGA
LaGuardia
$141 Roundtrip, found 2 days ago
$141
Roundtrip
found 2 days ago
Wed, Sep 2 - Wed, Sep 2
MCO
Orlando Intl.
ISP
MacArthur
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Tue, Oct 6 - Sat, Oct 10
MIA
Miami Intl.
LGA
LaGuardia
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Wed, Sep 23 - Tue, Oct 6
FLL
Fort Lauderdale - Hollywood Intl.
JFK
John F. Kennedy Intl.
$179 Roundtrip, found 4 hours ago
$179
Roundtrip
found 4 hours ago
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