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Wolfeboro Vacation Packages

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Wolfeboro Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $676, price is now $548 per person
$548
per person
Jan 24 - Jan 27
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lebanon (LEB)
Stay at this resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,501, price is now $1,117 per person
$1,117
per person
Jan 29 - Feb 2
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
River View Resort

River View Resort

2.5 out of 5
Price was $870, price is now $678 per person
$678
per person
Mar 1 - Mar 5
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and 4 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $922, price is now $738 per person
$738
per person
Feb 12 - Feb 15
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 Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $820, price is now $671 per person
$671
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,043, price is now $864 per person
$864
per person
Feb 12 - Feb 15
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 concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Price was $959, price is now $837 per person
$837
per person
Jan 29 - Feb 2
found 12 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 Neal S. Dow House and Center for Cultural Exchange are located nearby.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $840, price is now $734 per person
$734
per person
Feb 12 - Feb 15
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 N.W. Barrett Gallery and Fore Street Gallery are located nearby.

Wolfeboro 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 $681, price is now $546 per person
$546
per person
Mar 1 - Mar 5
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,501, price is now $1,117 per person
$1,117
per person
Jan 29 - Feb 2
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $738, price is now $566 per person
$566
per person
Mar 1 - Mar 5
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
River View Resort

River View Resort

2.5 out of 5
Price was $870, price is now $678 per person
$678
per person
Mar 1 - Mar 5
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)

Wolfeboro 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 $538, price is now $469 per person
$469
per person
Feb 1 - Feb 6
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $673, price is now $532 per person
$532
per person
Feb 1 - Feb 6
found 22 hours ago
Roundtrip non-stop 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 $739, price is now $624 per person
$624
per person
Feb 1 - Feb 6
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $585, price is now $515 per person
$515
per person
Feb 1 - Feb 6
found 1 hour ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)

Top Flight Deals

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

Bargain Flight
Tue, Jan 13 - Sun, Jan 18
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$184 Roundtrip, found 19 hours ago
$184
Roundtrip
found 19 hours ago
Select Bargain Flight flight, departing Tue, Jan 13 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sun, Jan 18, priced at $184 found 19 hours ago
American Airlines
Wed, May 27 - Thu, May 28
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$187 Roundtrip, found 21 hours ago
$187
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Thu, May 28, priced at $187 found 21 hours ago
Bargain Flight
Wed, Feb 18 - Tue, Feb 24
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Feb 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Feb 24, priced at $199 found 1 day ago
Breeze Airways
Fri, Feb 6 - Sun, Feb 8
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Feb 6 from Tampa Intl. to Portland Intl. Jetport, returning Sun, Feb 8, priced at $257 found 2 days ago