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Westport Vacation Packages

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Westport Flight + Hotel Packages

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

Amsterdam Hotel

2 out of 5
Price was $481, price is now $423 per person
$423
per person
Jan 28 - Feb 1
found 18 hours ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stamford Town Center and Stamford Public Library - Ferguson Library are located nearby.
The hotel was a tremendous value. Immaculate. Big room with Microwave, mini-fridge, and chair with 2 tables. Lots of TV channels. Abundance of towels. Cleaned the room every day although many places no longer do. Although we did not use them, there was a gym and business center. Adjacent free parking in heart of Stamford. Elevator. The night we arrived, the man at the desk even came up to the room to help me understand the tv.

Reviewed on Nov 15, 2026

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was $738, price is now $599 per person
$599
per person
Jan 15 - Jan 18
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Westchester County Center and Lyndhurst Mansion are located nearby.

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was $2,012, price is now $1,667 per person
$1,667
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Book a stay at this beach hotel in Greenwich. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Capitol Theatre and Greenwich Ferry Dock are located nearby.

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
Price was $730, price is now $617 per person
$617
per person
Jan 15 - Jan 18
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Capitol Theatre and E. Gaynor Brennan Golf Course are located nearby.
This hotel transports you to a different space entirely - great indoor views and semi tropical vibes

Reviewed on Nov 14, 2026

Westchester Marriott

Westchester Marriott

4.5 out of 5
Price was $1,208, price is now $1,052 per person
$1,052
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Book a stay at this spa hotel in Tarrytown. Enjoy free parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westchester County Center and Orange Trailhead are located nearby.

Residence Inn Stamford Downtown

Residence Inn Stamford Downtown

3 out of 5
Price was $1,299, price is now $1,139 per person
$1,139
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to White Plains (HPN)
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and a free beach shuttle. Popular attractions Stamford Center for the Arts and Stamford Public Library - Ferguson Library are located nearby.
This was a very nice hotel and the staff were very friendly and helpful.

Reviewed on Nov 9, 2026

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
Price was $616, price is now $543 per person
$543
per person
Jan 15 - Jan 18
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Book a stay at this business-friendly hotel in New Rochelle. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New Roc City and Glen Island Park are located nearby.
Price was great since parking was included. Served our purpose for our short stay. Beds were comfortable, clean room. Carpets everywhere which I'm not used to, hope they clean them properly and on a regular basis. Staff were friendly and helpful. Short walk to LIRR trains to Grand Central. Short walk to restaurants. Would definitely stay here again.

Reviewed on Nov 11, 2026

Westport Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was $738, price is now $599 per person
$599
per person
Jan 15 - Jan 18
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was $1,554, price is now $1,302 per person
$1,302
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
Price was $730, price is now $617 per person
$617
per person
Jan 15 - Jan 18
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)

Westport Vacation Packages 5-7 Night Stays

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

Stamford Marriott

3.5 out of 5
Downtown Stamford
Price was $1,115, price is now $913 per person
$913
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to White Plains (HPN)
Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was $2,012, price is now $1,667 per person
$1,667
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Westchester Marriott

Westchester Marriott

4.5 out of 5
Price was $1,208, price is now $1,052 per person
$1,052
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Residence Inn Stamford Downtown

Residence Inn Stamford Downtown

3 out of 5
Downtown Stamford
Price was $1,299, price is now $1,139 per person
$1,139
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to White Plains (HPN)

Top Flight Deals

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

Avelo Airlines
Fri, Dec 11 - Sun, Dec 13
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$143 Roundtrip, just found
$143
Roundtrip
just found
Select Avelo Airlines flight, departing Fri, Dec 11 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Dec 13, priced at $143 just found
Avelo Airlines
Fri, Dec 11 - Sun, Dec 13
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$143 Roundtrip, found 4 days ago
$143
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Fri, Dec 11 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Dec 13, priced at $143 found 4 days ago
Avelo Airlines
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$143 Roundtrip, found 3 hours ago
$143
Roundtrip
found 3 hours ago
Select Avelo Airlines flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $143 found 3 hours ago
Breeze Airways
Sat, Dec 26 - Mon, Jan 11
DJT
President Donald J. Trump Intl. Airport
HVN
Tweed - New Haven Regional
$155 Roundtrip, found 4 days ago
$155
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Dec 26 from President Donald J. Trump Intl. Airport to Tweed - New Haven Regional, returning Mon, Jan 11, priced at $155 found 4 days ago