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Long Island Vacation Packages

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Long Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Casco Bay Inn

Casco Bay Inn

2 out of 5
Price was $321, price is now $291 per person
$291
per person
Dec 4 - Dec 7
found 6 hours ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LL Bean Flagship Store and Eartha are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,370, price is now $1,122 per person
$1,122
per person
Dec 25 - Dec 28
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this 4.5-star luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ogunquit Beach and Perkins Cove are located nearby.
Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was $954, price is now $813 per person
$813
per person
Dec 24 - Dec 28
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 3-star B&B in Fryeburg. Enjoy free WiFi, free parking, and a garden. Popular attractions Fryeburg Public Library and Bradley Memorial Park are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $709, price is now $606 per person
$606
per person
Jan 1 - Jan 4
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Snowvillage Inn

Snowvillage Inn

4 out of 5
Price was $1,247, price is now $1,067 per person
$1,067
per person
Dec 24 - Dec 28
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4-star beach B&B in Eaton Center. Enjoy free WiFi, free parking, and a garden. Popular attractions King Pine Ski Area and Conway Lake are located nearby.
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Price was $874, price is now $765 per person
$765
per person
Jan 1 - Jan 4
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Inn on Shore Road

Inn on Shore Road

2 out of 5
Price was $997, price is now $902 per person
$902
per person
Dec 25 - Dec 28
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this inn in Ogunquit. Enjoy free breakfast, free WiFi, and housekeeping. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $914, price is now $829 per person
$829
per person
Jan 1 - Jan 4
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4-star luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

Long Island Vacation Packages 3-4 Night Stays

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $709, price is now $606 per person
$606
per person
Jan 1 - Jan 4
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,370, price is now $1,122 per person
$1,122
per person
Dec 25 - Dec 28
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was $954, price is now $813 per person
$813
per person
Dec 24 - Dec 28
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Snowvillage Inn

Snowvillage Inn

4 out of 5
Price was $1,247, price is now $1,067 per person
$1,067
per person
Dec 24 - Dec 28
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)

Long Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
Price was $814, price is now $761 per person
$761
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The Docent's Collection - New Opening

The Docent's Collection - New Opening

2 out of 5
Downtown Portland
Price was $1,167, price is now $1,058 per person
$1,058
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,584, price is now $1,461 per person
$1,461
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Portland (PWM)
The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Price was $1,109, price is now $1,034 per person
$1,034
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Wed, Nov 19 - Wed, Dec 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$172 Roundtrip, found 17 hours ago
$172
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Wed, Nov 19 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 3, priced at $172 found 17 hours ago
Delta
Mon, Nov 10 - Sat, Nov 15
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$182 Roundtrip, found 4 days ago
$182
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Nov 10 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Nov 15, priced at $182 found 4 days ago
American Airlines
Thu, Jan 15 - Mon, Jan 19
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Jan 15 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Mon, Jan 19, priced at $189 found 3 days ago
United
Thu, Nov 27 - Wed, Dec 3
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
Select United flight, departing Thu, Nov 27 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Dec 3, priced at $212 found 2 days ago