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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.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,060, price is now $765 per person
$765
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Our room

Reviewed on Sep 12, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Save 100% on your flight
Price was $3,608, price is now $2,683 per person
$2,683
per person
Oct 17 - Oct 24
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 Thompson's Point are located nearby.
Room was beautiful, new, and clean. Staff upon check in was extremely helpful and courteous, Excellent accommodations. Close to many sights, bars, and restaurants. Would stay again in a heartbeat.

Reviewed on Sep 12, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Price was $1,391, price is now $1,050 per person
$1,050
per person
Dec 3 - Dec 8
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 Thompson's Point are located nearby.

Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was $1,037, price is now $805 per person
$805
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Fryeburg. Enjoy free WiFi, free parking, and a garden. Popular attractions Fryeburg Public Library and Bradley Memorial Park are located nearby.

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $2,318, price is now $1,802 per person
$1,802
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Portland Head Light and Crescent Beach State Park are located nearby.
Beautiful location, quiet, but close to beach and shorelines. Lots of thoughtful luxuries provided like beach chairs, buckets, snacks, fruit and a nightly fire with smores.

Reviewed on Sep 11, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,650, price is now $1,285 per person
$1,285
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip 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 Ogunquit Beach and Perkins Cove are located nearby.

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,001, price is now $783 per person
$783
per person
Dec 3 - Dec 8
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 Thompson's Point are located nearby.

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $1,205, price is now $949 per person
$949
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
Negatives - Water mark and black mold on ceiling Loose toilet Dirty carpet Positive Great staff Great breakfast

Reviewed on Sep 13, 2026

Wolfeboro Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,060, price is now $765 per person
$765
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,161, price is now $898 per person
$898
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was $1,650, price is now $1,285 per person
$1,285
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,292, price is now $1,034 per person
$1,034
per person
Oct 27 - Oct 30
just found
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Wolfeboro Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was $1,037, price is now $805 per person
$805
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $3,608, price is now $2,683 per person
$2,683
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,178, price is now $877 per person
$877
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was $1,391, price is now $1,050 per person
$1,050
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$180 Roundtrip, found 1 hour ago
$180
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $180 found 1 hour ago
Breeze Airways
Fri, Nov 13 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$197 Roundtrip, found 21 hours ago
$197
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Fri, Nov 13 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at $197 found 21 hours ago
Breeze Airways
Sat, Nov 14 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$225 Roundtrip, found 10 hours ago
$225
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Sat, Nov 14 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $225 found 10 hours ago
Bargain Flight
Mon, Sep 28 - Sat, Oct 10
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Mon, Sep 28 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Oct 10, priced at $277 found 4 days ago