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Lakes and Mountains Vacation Packages

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Lakes and Mountains Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Price was $497, price is now $404 per person
$404
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Portland Stage are located nearby.
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $672, price is now $476 per person
$476
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fort Preble and Portland Harbor Museum are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $714, price is now $539 per person
$539
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,794, price is now $1,387 per person
$1,387
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Greensboro (GSO) to Portland (PWM)
Book a stay at this 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 Perkins Cove and Marginal Way are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $885, price is now $710 per person
$710
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $771, price is now $626 per person
$626
per person
Mar 12 - Mar 15
found 1 day 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 Cross Insurance Arena and Fore Street Gallery are located nearby.
84 Main

84 Main

4 out of 5
Price was $708, price is now $575 per person
$575
per person
Mar 12 - Mar 15
found 1 day 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.
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Price was $523, price is now $426 per person
$426
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Maine Jewish Museum and Maine Narrow Gauge Railroad Company and Museum are located nearby.

Lakes and Mountains Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $672, price is now $476 per person
$476
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $714, price is now $539 per person
$539
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was $1,794, price is now $1,387 per person
$1,387
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Greensboro (GSO) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $885, price is now $710 per person
$710
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)

Lakes and Mountains Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
84 Main

84 Main

4 out of 5
Save 100% on your flight
Price was $562, price is now $372 per person
$372
per person
Mar 13 - Mar 18
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $932, price is now $699 per person
$699
per person
Mar 13 - Mar 18
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $659, price is now $497 per person
$497
per person
Mar 13 - Mar 18
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
Price was $726, price is now $553 per person
$553
per person
Mar 13 - Mar 18
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)

Top Flight Deals

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

American Airlines
Wed, May 27 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Jun 5, priced at $173 found 1 day ago
Delta
Fri, Mar 6 - Wed, Mar 11
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Mar 6 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Mar 11, priced at $209 found 1 day ago
Breeze Airways
Mon, May 18 - Wed, May 27
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, May 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, May 27, priced at $217 found 1 day ago
United
Mon, Feb 9 - Thu, Feb 12
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select United flight, departing Mon, Feb 9 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Thu, Feb 12, priced at $217 found 1 day ago