Search Deals onWolfeboro Vacation Packages
Wolfeboro Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street
Price was $864, price is now $685 per person
$685
per person
Dec 3 - Dec 5
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.
Great place and location to everything. Very cool building and modern. Staff was great.
Reviewed on Sep 25, 2026
Green Trails Inn
Price was $1,009, price is now $729 per person
$729
per person
Dec 2 - Dec 10
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Lebanon (LEB)
Stay at this inn in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Brookfield Free Public Library and Allis State Park are located nearby.
Everything
Reviewed on Sep 15, 2026
Portland Harbor Hotel
Price was $1,381, price is now $1,003 per person
$1,003
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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 Thompson's Point are located nearby.
Blind Tiger Portland - Danforth Street.
Price was $1,738, price is now $1,405 per person
$1,405
per person
Nov 4 - Nov 8
found 9 hours ago
Roundtrip 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.
Place was charming and quirky. Very comfortable and well located.
Reviewed on Sep 18, 2026
Evalina Hotel
Price was $1,250, price is now $1,013 per person
$1,013
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip 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 Maine Mall are located nearby.
This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class.
Reviewed on Sep 24, 2026
Blind Tiger Portland – Carleton Street
Price was $1,601, price is now $1,321 per person
$1,321
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Beautiful place
Reviewed on Sep 20, 2026
Hanover Inn Dartmouth
Save 100% on your flight
Price was $2,255, price is now $1,884 per person
$1,884
per person
Dec 2 - Dec 10
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Lebanon (LEB)
Book a stay at this luxury hotel in Hanover. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Hopkins Center for the Arts and Left Bank Books are located nearby.
Six South St Hotel
Price was $1,302, price is now $1,091 per person
$1,091
per person
Dec 2 - Dec 10
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Lebanon (LEB)
Stay at this hotel in Hanover. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Black Family Visual Arts Center and Left Bank Books are located nearby.
There is no real breakfast to speak of other than ready made muffins and bagels with a toaster. Plenty of places to eat outside of hotel and a coffee machine in room makes better coffee. Rooms are always clean. Bar and coffee bar not open. Restaurant only Tuesday to Saturday
Reviewed on Sep 20, 2026
Wolfeboro Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Wolfeboro 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.
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 7 hours ago
$144
Roundtrip
found 7 hours ago
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 6 hours ago
$185
Roundtrip
found 6 hours ago
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$213 Roundtrip, found 4 hours ago
$213
Roundtrip
found 4 hours ago
Tue, Oct 20 - Sat, Oct 31
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$301 Roundtrip, found 2 days ago
$301
Roundtrip
found 2 days ago
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