Search Deals onWestbrook Vacation Packages
Westbrook Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
84 Main
Price was $1,200, price is now $940 per person
$940
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Wells Beach are located nearby.
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.
Reviewed on Jul 17, 2026
The Docent's Collection at 121 Middle Street
Price was $1,974, price is now $1,512 per person
$1,512
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Amazing location and lots of space in Portland Maine. We loved it!!
Reviewed on Oct 14, 2026
Inn By The Sea
Price was $1,691, price is now $1,329 per person
$1,329
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
We had a wonderful stay at Inn By the Sea.
Reviewed on Oct 15, 2026
Canopy by Hilton Portland Waterfront
Price was $1,537, price is now $1,259 per person
$1,259
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
This hotel is perfectly located to enjoy all the restaurants and shops along the waterfront and downtown.
The hotel practices environmentally friendly practices with refillable water carafes and provided toiletries.
The staff goes above and beyond, even after you've checked out.
10/10
Reviewed on Oct 15, 2026
Portland Regency Hotel & Spa
Price was $1,171, price is now $964 per person
$964
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Extremely well located in Portland, in the heart of the old town and central to everything. I'm glad we chose this hotel rather than others that were mostly newer. The breakfast and bar options were good.
Reviewed on Oct 15, 2026
Blind Tiger Portland - Danforth Street.
Price was $1,882, price is now $1,575 per person
$1,575
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
The Docent's Collection at 178 Middle Street
Price was $2,105, price is now $1,776 per person
$1,776
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Longfellow Hotel
Price was $1,455, price is now $1,246 per person
$1,246
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
Westbrook Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Westbrook 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, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$184 Roundtrip, found 16 hours ago
$184
Roundtrip
found 16 hours ago
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$194 Roundtrip, found 9 hours ago
$194
Roundtrip
found 9 hours ago
Tue, Nov 10 - Wed, Nov 18
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$206 Roundtrip, found 9 hours ago
$206
Roundtrip
found 9 hours ago
Thu, Dec 3 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 11 hours ago
$207
Roundtrip
found 11 hours ago
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