Search Deals onWolfeboro Vacation Packages
Wolfeboro Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Kennebunk Inn
Price was $878, price is now $831 per person
$831
per person
Dec 31 - Jan 5
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Kennebunk. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
Kennebunkport Captains Collection
Price was $1,485, price is now $1,201 per person
$1,201
per person
Dec 31 - Jan 5
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Kennebunkport Village Green are located nearby.
Amazing place for our Mini Moon! Would definitely recommend
Reviewed on Nov 13, 2026
Inn By The Sea
Price was $1,401, price is now $1,194 per person
$1,194
per person
Dec 31 - Jan 5
found 20 hours ago
Roundtrip 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.
Canopy by Hilton Portland Waterfront
Price was $1,336, price is now $1,168 per person
$1,168
per person
Dec 31 - Jan 5
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, 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.
We highly enjoyed our stay here! Great restaurant downstairs, very clean, and helpful kind staff! Wish we could stay longer!
Reviewed on Nov 12, 2026
InnSeason Resorts The Falls at Ogunquit
Price was $974, price is now $865 per person
$865
per person
Dec 28 - Jan 3
found 9 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Footbridge Beach and Ogunquit Beach are located nearby.
The Kendall Inn
Price was $965, price is now $860 per person
$860
per person
Dec 31 - Jan 5
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.
Follansbee Inn
Price was $1,396, price is now $1,316 per person
$1,316
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Lebanon (LEB)
Book a stay at this beach B&B in Sutton. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Country Club Of New Hampshire and Wadleigh State Park are located nearby.
If you are looking for a quiet stay in the middle of the NH Lake Sunapee region, this is your place. From the moment we stepped into the Inn to the time we left, it was a great experience. The game closet was full with fun games and the other guests we met were great to hang out with. No TV made everyone actually talk to each other and learn about each other. The chairs by the lake are great for that afternoon nap or just watch nature and read a book. The room was comfortable and the bed was amazing. As someone with a bad back, this was huge! This is on our "we will return" list for places to stay!
Reviewed on Oct 20, 2026
Dowds Country Inn
Price was $1,241, price is now $1,184 per person
$1,184
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Lebanon (LEB)
Stay at this B&B in Lyme. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lyme Common and Matt Brown Fine Art are located nearby.
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.
Mon, Feb 15 - Sat, Feb 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$224 Roundtrip, found 1 hour ago
$224
Roundtrip
found 1 hour ago
Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$256 Roundtrip, just found
$256
Roundtrip
just found
Sun, Feb 28 - Wed, Mar 10
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$267 Roundtrip, found 16 hours ago
$267
Roundtrip
found 16 hours ago
Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
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