Search Deals onPeaks Island Vacation Packages
Peaks Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Portland Harbor Hotel
Price was $1,252, price is now $1,042 per person
$1,042
per person
Dec 26 - Jan 1
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
The staff was very friendly and the hotel was very quaint. It was also in the perfect location.
Reviewed on Nov 15, 2026

Blind Tiger Portland - Danforth Street.
Price was $2,849, price is now $2,217 per person
$2,217
per person
Dec 26 - Jan 1
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Cross Insurance Arena are located nearby.

The Docent's Collection at 121 Middle Street
Price was $1,897, price is now $1,544 per person
$1,544
per person
Dec 26 - Jan 1
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.

Blind Tiger Portland – Carleton Street
Price was $1,568, price is now $1,288 per person
$1,288
per person
Dec 26 - Jan 1
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions State Theatre and Cross Insurance Arena are located nearby.

Inn By The Sea
Price was $1,964, price is now $1,613 per person
$1,613
per person
Dec 26 - Jan 1
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

84 Main
Price was $1,322, price is now $1,096 per person
$1,096
per person
Dec 20 - Dec 23
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Kennebunk Free Library 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

Evalina Hotel
Price was $2,116, price is now $1,842 per person
$1,842
per person
Dec 26 - Jan 1
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions State Theatre and Thompson's Point are located nearby.

Portland Regency Hotel & Spa
Price was $1,260, price is now $1,115 per person
$1,115
per person
Dec 26 - Jan 1
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 State Theatre and Thompson's Point are located nearby.
Can’t beat the location! If you’re planning to spend the day wandering shops, restaurants, bakeries, and bars in Portland, it’s a short walk to/from everything. Made it easy to quickly drop things in the room. Room itself was big and the bed was comfortable. Bathroom was a little on the small side, but the shower was really nice. There’s a little whiskey bar with a fireplace that they open in the evening which was a great place to grab a quick drink before dinner.
Reviewed on Nov 15, 2026
Peaks Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Peaks Island 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.

Mon, Feb 15 - Sat, Feb 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$224 Roundtrip, just found
$224
Roundtrip
just found

Sun, Feb 28 - Wed, Mar 10
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$247 Roundtrip, found 1 hour ago
$247
Roundtrip
found 1 hour ago

Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$275 Roundtrip, found 1 hour ago
$275
Roundtrip
found 1 hour ago

Wed, Dec 2 - Sat, Dec 5
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$363 Roundtrip, found 5 days ago
$363
Roundtrip
found 5 days ago
Discover Other Travel Deals
- Maine Mall Vacations
- LL Bean Flagship Store Vacations
- State Theatre Vacations
- Old Orchard Beach Pier Vacations
- Thompson's Point Vacations
- Portland Head Light Vacations
- Cross Insurance Arena Vacations
- Maine Medical Center Vacations
- Higgins Beach Vacations
- Portland Museum of Art Vacations
- University of New England Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations


