Search Deals onWolfeboro Vacation Packages
Wolfeboro Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland
Price was $486, price is now $381 per person
$381
per person
Sep 6 - Sep 9
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, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Easy place to find, quick check-in, clean room, lots of places to eat, interstate 95 close by. Very happy with my choice!
Reviewed on Jul 16, 2026
Blind Tiger Portland – Carleton Street
Save 100% on your flight
Price was $1,601, price is now $1,024 per person
$1,024
per person
Sep 6 - Sep 9
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 daily housekeeping. Popular attractions State Theatre and Thompson's Point are located nearby.
Excellent private boutique home, converted to hotel. No person greets you and there is no welcome desk. You put in a code on the door to enter and instructions are given via text. No elevator and 3 stories, so keep that in mind. Would HIGHLY recommend.
Reviewed on Jul 16, 2026
Blind Tiger Portland - Danforth Street.
Save 100% on your flight
Price was $1,306, price is now $837 per person
$837
per person
Sep 6 - Sep 9
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 parking (surcharge). Popular attractions State Theatre and Cross Insurance Arena are located nearby.
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.
Reviewed on Jun 26, 2026
Inn at Diamond Cove
Save 100% on your flight
Price was $1,463, price is now $974 per person
$974
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Casco Bay Lines Ferry Terminal and State Theatre are located nearby.
Unusual place to stay; in a renovated former army base. Huge rooms, gorgeous recent renovation/reconstruction.Expensive!
Reviewed on Jul 12, 2026
Evalina Hotel
Save 100% on your flight
Price was $1,630, price is now $1,123 per person
$1,123
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop 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 Casco Bay Lines Ferry Terminal are located nearby.
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.
Reviewed on Jun 28, 2026
The Docent's Collection at 121 Middle Street
Save 100% on your flight
Price was $1,009, price is now $735 per person
$735
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Cross Insurance Arena and State Theatre are located nearby.
Beautiful place to stay
Reviewed on Jul 15, 2026
Portland Harbor Hotel
Save 100% on your flight
Price was $889, price is now $652 per person
$652
per person
Sep 6 - Sep 9
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 Casco Bay Lines Ferry Terminal and State Theatre are located nearby.
The hotel was centrally located in the vibrant Portland downtown harbor district. It was an easy walk to the water, shops and countless restaurants. The rooms were spacious and comfortable and the staff was very helpful
Reviewed on Jul 18, 2026
The Docent's Collection at 178 Middle Street
Save 100% on your flight
Price was $1,090, price is now $856 per person
$856
per person
Sep 6 - Sep 9
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 Cross Insurance Arena and State Theatre are located nearby.
room was beautiful!! staff was very helpful & friendly, comfy beds, great location!! walk to waterfront, shopping & dining. if you are in Ole Port , this is the best!!
Reviewed on Jul 17, 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.
Wed, Sep 16 - Wed, Sep 23
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Tue, Sep 8 - Sat, Sep 12
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$200 Roundtrip, found 5 hours ago
$200
Roundtrip
found 5 hours ago
Wed, Aug 5 - Sat, Aug 22
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
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