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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.
The Stamford Hotel

The Stamford Hotel

3.5 out of 5
Price was $429, price is now $334 per person
$334
per person
Oct 20 - Oct 22
found 1 day 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.

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Save 100% on your flight
Price was $3,112, price is now $2,179 per person
$2,179
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Book a stay at this business-friendly vacation home in Yonkers. Enjoy free WiFi, free parking, and dry cleaning or laundry services. Popular attractions Bronx Zoo and Empire City Casino are located nearby.

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.5 out of 5
Save 100% on your flight
Price was $2,693, price is now $2,073 per person
$2,073
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Stay at this vacation home in Yonkers. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Yankee Stadium and Bronx Zoo are located nearby.
Publicación totalmente falsa, fotos falsas. El lugar no es como lo muestran, no te dan TODO el apartamento como mencionan, te lo dan dividido, nunca más rentaría de nuevo este lugar!

Reviewed on Jul 22, 2026

Spacious Retreat with Game Room

Spacious Retreat with Game Room

2.5 out of 5
Save 100% on your flight
Price was $713, price is now $557 per person
$557
per person
Oct 20 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Book a stay at this golf lodge in Norwalk. Enjoy free WiFi, free parking, and a garden. Popular attractions Waveny Park and Woodway Park are located nearby.
This was one of the best locations I’ve stayed at in the last year or so, 5 stars across the board in every category. Communications with the host was outstanding as well. I highly recommend staying here. I wish I could’ve stayed more than one night.

Reviewed on Mar 30, 2026

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Save 100% on your flight
Price was $987, price is now $772 per person
$772
per person
Oct 20 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 Greenwich Avenue and Rye Playland are located nearby.
The hotel was wonderful and I would recommend it to anyone. We took an uber into NYC. The area is beautiful with many things to.

Reviewed on Jul 26, 2026

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

2 out of 5
Price was $528, price is now $415 per person
$415
per person
Oct 20 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.

Family Cottage with 4 King Beds

Family Cottage with 4 King Beds

2.5 out of 5
Price was $583, price is now $462 per person
$462
per person
Oct 20 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
Book a stay at this golf lodge in Norwalk. Enjoy free WiFi, free parking, and a garden. Popular attractions Norwalk Islands and East Norwalk Historical Cemetery are located nearby.

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was $722, price is now $576 per person
$576
per person
Sep 17 - Sep 20
found 23 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.
Great stay, beautiful property. Look forward to coming again!

Reviewed on Jul 28, 2026

Westport Vacation Packages 3-4 Night Stays

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

Stamford Suites

4 out of 5
Downtown Stamford
Price was $650, price is now $531 per person
$531
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $3,112, price is now $2,179 per person
$2,179
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.5 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $2,693, price is now $2,073 per person
$2,073
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was $722, price is now $576 per person
$576
per person
Sep 17 - Sep 20
found 23 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.
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
Downtown Stamford
Price was $684, price is now $554 per person
$554
per person
Oct 10 - Oct 17
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking

2 out of 5
Save 100% on your flight
Price was $3,131, price is now $2,425 per person
$2,425
per person
Sep 3 - Sep 8
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,333, price is now $1,103 per person
$1,103
per person
Sep 3 - Sep 8
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Price was $953, price is now $793 per person
$793
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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
Wed, Sep 2 - Wed, Sep 2
MCO
Orlando Intl.
ISP
MacArthur
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Orlando Intl. to MacArthur, returning Wed, Sep 2, priced at $128 found 2 days ago
Breeze Airways
Tue, Aug 4 - Tue, Aug 25
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$153 Roundtrip, found 3 days ago
$153
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Aug 4 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Aug 25, priced at $153 found 3 days ago
Avelo Airlines
Fri, Aug 14 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$154 Roundtrip, just found
$154
Roundtrip
just found
Select Avelo Airlines flight, departing Fri, Aug 14 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Aug 23, priced at $154 just found
Breeze Airways
Thu, Sep 10 - Thu, Sep 10
TPA
Tampa Intl.
ISP
MacArthur
$213 Roundtrip, found 12 hours ago
$213
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Tampa Intl. to MacArthur, returning Thu, Sep 10, priced at $213 found 12 hours ago