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Woolwich Vacation Packages

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Woolwich 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
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)
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

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,517, price is now $913 per person
$913
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 Marginal Way are located nearby.
Room was very comfortable. A/C worked too well! Easy check in. Would stay here again definitely. Worth the extra cost for balcony room.

Reviewed on Jul 16, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,967, price is now $1,323 per person
$1,323
per person
Oct 9 - Oct 12
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) 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

Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
Save 100% on your flight
Price was $1,573, price is now $1,188 per person
$1,188
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Augusta (AUG)
Book a stay at this beach hotel in East Boothbay. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Coastal Maine Botanical Gardens and Grimes Cove Beach are located nearby.
Beautiful location. Quirky quaint property.

Reviewed on Jul 16, 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 9 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

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,532, price is now $1,172 per person
$1,172
per person
Oct 9 - Oct 12
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) 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.

Harborline Hotel

Harborline Hotel

3 out of 5
Save 100% on your flight
Price was $1,146, price is now $878 per person
$878
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Rockland (RKD)
Stay at this hotel in Rockland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Samoset Resort Golf Course and Maine Lighthouse Museum are located nearby.

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,348, price is now $1,046 per person
$1,046
per person
Oct 9 - Oct 12
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) 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

Woolwich 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 $1,967, price is now $1,323 per person
$1,323
per person
Oct 9 - Oct 12
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) 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 9 hours ago
Roundtrip flight included
Columbus (CMH) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,532, price is now $1,172 per person
$1,172
per person
Oct 9 - Oct 12
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)

Woolwich Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,517, price is now $913 per person
$913
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $3,530, price is now $2,143 per person
$2,143
per person
Sep 20 - Sep 27
found 7 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
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)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,540, price is now $1,822 per person
$1,822
per person
Sep 20 - Sep 27
found 7 hours ago
Roundtrip flight included
Baltimore (BWI) 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