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Old Greenwich Vacation Packages

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Old Greenwich Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Highland Ave

Highland Ave

2 out of 5
Price was $533, price is now $445 per person
$445
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Stay at this apartment in Norwalk. Enjoy free WiFi and free parking. Popular attractions SoNo Switch Tower Museum and Historic South Norwalk are located nearby.
Very convenient to where I needed to be. Once I was able to get on the internet everything was good

Reviewed on Jul 18, 2026

The Stamford Hotel

The Stamford Hotel

3.5 out of 5
Price was $699, price is now $534 per person
$534
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Book a stay at this business-friendly hotel in Stamford. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenwich Avenue and Stamford Town Center are located nearby.
Super clean and comfortable! Convenient location just outside of downtown.

Reviewed on Jul 22, 2026

Delamar Southport

Delamar Southport

4 out of 5
Save 100% on your flight
Price was $1,069, price is now $825 per person
$825
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) 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

Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa

3.5 out of 5
Price was $830, price is now $655 per person
$655
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) 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 Greenwich Avenue and Stamford Town Center are located nearby.

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

2 out of 5
Price was $823, price is now $669 per person
$669
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
Stay at this apartment in Yonkers. Enjoy free WiFi and free parking. Popular attractions Westchester's Ridge Hill and Legoland Discovery Center Westchester are located nearby.

Hampton Inn Danbury

Hampton Inn Danbury

2.5 out of 5
Price was $728, price is now $606 per person
$606
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) 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 helpful staff and the clean rooms in our reviews. Popular attractions Candlewood Lake and Still River Greenway are located nearby.
Staff was wonderful and room very comfortable and CLEAN.

Reviewed on Jul 22, 2026

Stamford Suites

Stamford Suites

4 out of 5
Price was $825, price is now $712 per person
$712
per person
Sep 4 - Sep 7
found 21 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Hotel is in very bad shape -Peeling paint everywhere - stained carpets - musty smells Stay Away

Reviewed on Jul 21, 2026

Stanton House Inn

Stanton House Inn

3.5 out of 5
Price was $1,068, price is now $923 per person
$923
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Stay at this B&B in Greenwich. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Greenwich Avenue and Rye Playland are located nearby.
A very pleasant stay with a wonderful pool in summer.

Reviewed on Jul 2, 2026

Old Greenwich Vacation Packages 3-4 Night Stays

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

The Stamford Hotel

3.5 out of 5
Downtown Stamford
Price was $699, price is now $534 per person
$534
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Delamar Southport

Delamar Southport

4 out of 5
Save 100% on your flight
Price was $1,069, price is now $825 per person
$825
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa

3.5 out of 5
Downtown Stamford
Price was $830, price is now $655 per person
$655
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

2 out of 5
Bryn Mawr
Price was $823, price is now $669 per person
$669
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)

Old Greenwich Vacation Packages 5-7 Night Stays

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

Amsterdam Hotel

2 out of 5
Downtown Stamford
Price was $636, price is now $542 per person
$542
per person
Oct 14 - Oct 19
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to White Plains (HPN)
Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
Save 100% on your flight
Price was $1,171, price is now $889 per person
$889
per person
Sep 5 - Sep 12
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
Save 100% on your flight
Price was $984, price is now $794 per person
$794
per person
Sep 5 - Sep 12
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
Price was $741, price is now $609 per person
$609
per person
Sep 6 - Sep 11
found 15 hours ago
Roundtrip flight included
Dallas (DAL) to White Plains (HPN)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Nov 3 - Mon, Nov 9
MCO
Orlando Intl.
LGA
LaGuardia
$98 Roundtrip, found 16 hours ago
$98
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, Nov 3 from Orlando Intl. to LaGuardia, returning Mon, Nov 9, priced at $98 found 16 hours ago
Frontier Airlines
Wed, Sep 2 - Wed, Sep 2
MCO
Orlando Intl.
ISP
MacArthur
$159 Roundtrip, just found
$159
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Sep 2 from Orlando Intl. to MacArthur, returning Wed, Sep 2, priced at $159 just found
JetBlue Airways
Tue, Aug 25 - Tue, Aug 25
FLL
Fort Lauderdale - Hollywood Intl.
LGA
LaGuardia
$176 Roundtrip, found 2 days ago
$176
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Fort Lauderdale - Hollywood Intl. to LaGuardia, returning Tue, Aug 25, priced at $176 found 2 days ago
Delta
Tue, Oct 6 - Sat, Oct 10
MIA
Miami Intl.
LGA
LaGuardia
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 6 from Miami Intl. to LaGuardia, returning Sat, Oct 10, priced at $179 found 2 days ago