Woolwich Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Woolwich Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $912, price is now $656 per person
$656
per person
Apr 18 - Apr 24
just found
Roundtrip flight included
Chicago (ORD) 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 Maine Mall and Cross Insurance Arena are located nearby.
Ogunquit River Inn & Suites
Price was $1,202, price is now $846 per person
$846
per person
May 21 - May 25
found 4 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
Cliff House Maine
Bald Head
Save 100% on your flight
Price was $2,484, price is now $1,881 per person
$1,881
per person
May 21 - May 25
found 4 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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 Perkins Cove and Marginal Way are located nearby.
Portland Regency Hotel & Spa
Downtown Portland
Price was $887, price is now $673 per person
$673
per person
Apr 18 - Apr 24
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Fore Street Gallery are located nearby.
Inn By The Sea
Save 100% on your flight
Price was $1,307, price is now $1,021 per person
$1,021
per person
Apr 18 - Apr 24
found 1 hour ago
Roundtrip flight included
Chicago (ORD) 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 Crescent Beach State Park and Crescent Beach are located nearby.
The Press Hotel, Marriott Autograph Collection
Downtown Portland
Price was $1,070, price is now $838 per person
$838
per person
Apr 18 - Apr 24
just found
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Maine Mall and Merrill Auditorium are located nearby.
Top Hotel Deals
SpringHill Suites by Marriott Freeport Brunswick
500 US-1 Freeport ME
27.37 km from city center
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Holiday Inn Express Hotel & Suites Freeport by IHG
450 U.S. Route 1 Freeport ME
27.65 km from city center
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Residence Inn Bath Brunswick Area
139 Richardson St. Bath ME
2.41 km from city center
Book a stay at this business-friendly hotel in Bath. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the property ...
Flagship Inn and Suites
200 Townsend Avenue Boothbay Harbor ME
15.33 km from city center
Stay at this hotel in Boothbay Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. Popular ...
The Federal
10 Water St Brunswick ME
12.98 km from city center
Stay at this hotel in Brunswick. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. ...
The Brunswick Hotel
4 Noble St Brunswick ME
12.97 km from city center
Book a stay at this business-friendly hotel in Brunswick. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
Fairfield Inn & Suites by Marriott Brunswick Freeport
36 Old Portland Rd Brunswick ME
16.18 km from city center
Book a stay at this business-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Best Western Plus Brunswick Bath
71 Gurnet Road Brunswick ME
8.98 km from city center
Book a stay at this family-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hilton Garden Inn Freeport Downtown
5 Park St Freeport ME
24.85 km from city center
Book a stay at this business-friendly hotel in Freeport. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
The Harraseeket Inn & Event House Freeport Downtown
162 Main St Freeport ME
24.82 km from city center
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Travelers Inn
130 Pleasant St Brunswick ME
14.56 km from city center
Book a stay at this business-friendly motel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hampton Inn Freeport/Brunswick
194 Lower Main St Freeport ME
26.56 km from city center
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
SureStay by Best Western Lewiston Auburn Area
516 Pleasant St Lewiston ME
34.92 km from city center
Stay at this hotel in Lewiston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Mon, May 25 - Fri, May 29
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Mon, May 4 - Wed, May 13
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Sun, May 24 - Sat, May 30
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Sat, Jun 6 - Sat, Jun 13
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$193 Roundtrip, found 3 days ago
$193
Roundtrip
found 3 days ago