Search Deals onWindham Vacation Packages
Windham Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Portland Regency Hotel & Spa
Price was $789, price is now $628 per person
$628
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip non-stop 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 Thompson's Point are located nearby.
Excellent location, great front of house staff. Historical building. Well designed rooms. Shuttle from airport.
Reviewed on Sep 15, 2026
The Docent's Collection at 121 Middle Street
Save 100% on your flight
Price was $1,227, price is now $895 per person
$895
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Hotel was great, big room with a full kitchen. Location is right where you want to be, super easy to walk anywhere in old port. The elevator made this cool little James Bond -beep- noise when I touched the hotel key to the reader.
Reviewed on Sep 17, 2026
Evalina Hotel
Price was $1,163, price is now $854 per person
$854
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Blind Tiger Portland – Carleton Street
Price was $1,311, price is now $978 per person
$978
per person
Dec 3 - Dec 8
found 16 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Blind Tiger Portland - Danforth Street.
Save 100% on your flight
Price was $1,350, price is now $1,018 per person
$1,018
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Thompson's Point and Portland Head Light are located nearby.
Enjoyable
Reviewed on Aug 28, 2026
The Meadowmere Resort
Price was $1,264, price is now $963 per person
$963
per person
Dec 10 - Dec 15
found 16 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
The Docent's Collection at 178 Middle Street
Price was $1,001, price is now $783 per person
$783
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip non-stop 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 Thompson's Point are located nearby.
Beautiful room and location. Didn't really use the amenities
Reviewed on Sep 14, 2026
Inn at St John Portland In-Town
Price was $991, price is now $814 per person
$814
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Cross Insurance Arena are located nearby.
The Inn was a charming place to stay with it's quirky room layouts and charming lobby. The staff was exceedingly helpful. It IS a hundred year old Inn so you need to expect the "charm" over modern upgrades. We found the breakfast to be convenient with a substantial selection. It was a little further from the Port area - just a warning if you plan on walking "into town" Lovely place and we thoroughly enjoyed our stay!!
Reviewed on Sep 17, 2026
Windham Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Windham 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.
Thu, Nov 26 - Wed, Dec 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 3 days ago
$185
Roundtrip
found 3 days ago
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Thu, Oct 8 - Fri, Oct 23
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 3 days ago
$277
Roundtrip
found 3 days ago
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