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Wiscasset Vacation Packages

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Wiscasset Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
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

Evalina Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,862, price is now $1,317 per person
$1,317
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Save 100% on your flight
Price was $1,847, price is now $1,405 per person
$1,405
per person
Sep 21 - Sep 24
found 6 hours ago
Roundtrip flight included
Columbus (CMH) 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

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,952, price is now $1,495 per person
$1,495
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Save 100% on your flight
Price was $1,309, price is now $1,032 per person
$1,032
per person
Sep 21 - Sep 24
found 6 hours ago
Roundtrip flight included
Columbus (CMH) 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

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,346, price is now $1,086 per person
$1,086
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,324, price is now $1,069 per person
$1,069
per person
Sep 21 - Sep 24
found 6 hours ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Higgins Beach and Portland Head Light are located nearby.

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,219, price is now $1,013 per person
$1,013
per person
Sep 21 - Sep 24
found 6 hours ago
Roundtrip flight included
Columbus (CMH) 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 Wells Beach are located nearby.
Everything about this property was perfect

Reviewed on Jul 17, 2026

Wiscasset Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was $953, price is now $688 per person
$688
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,862, price is now $1,317 per person
$1,317
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $1,847, price is now $1,405 per person
$1,405
per person
Sep 21 - Sep 24
found 6 hours ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,952, price is now $1,495 per person
$1,495
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)

Wiscasset Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
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)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,980, price is now $1,577 per person
$1,577
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
Valley Street
Price was $1,632, price is now $1,348 per person
$1,348
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $3,405, price is now $2,093 per person
$2,093
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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, 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
Select Breeze Airways flight, departing Wed, Sep 16 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, Sep 23, priced at $152 found 4 days ago
United
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
Select United flight, departing Tue, Sep 8 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, Sep 12, priced at $196 found 1 day ago
JetBlue Airways
Wed, Aug 5 - Sat, Aug 22
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$208 Roundtrip, found 1 day ago
$208
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Aug 5 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $208 found 1 day ago
Breeze Airways
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$213 Roundtrip, found 6 days ago
$213
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $213 found 6 days ago