Standish Vacations
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Standish Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove
Save 100% on your flight
Price was $1,039, price is now $712 per person
$712
per person
Sep 14 - Sep 18
found 17 hours ago
Roundtrip flight included
Chicago (CHI) 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
Downtown Portland
Save 100% on your flight
Price was $1,989, price is now $1,242 per person
$1,242
per person
Sep 14 - Sep 18
found 17 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Casco Bay Lines Ferry Terminal and State Theatre 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 Weldon Hotel
Downtown Portland
Save 100% on your flight
Price was $1,663, price is now $1,092 per person
$1,092
per person
Sep 14 - Sep 18
found 17 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions State Theatre and Casco Bay Lines Ferry Terminal are located nearby.
Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.
Reviewed on Jul 5, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
Save 100% on your flight
Price was $1,492, price is now $1,102 per person
$1,102
per person
Sep 14 - Sep 18
found 17 hours ago
Roundtrip flight included
Chicago (CHI) 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.
Great location. Clean great room. Recommend highly
Reviewed on Jul 6, 2026
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $1,482, price is now $1,102 per person
$1,102
per person
Aug 24 - Aug 29
found 19 hours ago
Roundtrip flight included
Columbus (CMH) 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.
Our stay was great - the location of this hotel is perfect, the staff was friendly and our room was really nice. Every morning, there was a fully stocked pantry with snacks and drinks for guests on each floor. We had a great stay and would recommend this place highly!
Reviewed on Jul 12, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Save 100% on your flight
Price was $1,393, price is now $1,073 per person
$1,073
per person
Sep 14 - Sep 18
found 17 hours ago
Roundtrip flight included
Chicago (CHI) 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.
The unit was clean and convenient. Very central, short walks to restaurants, harbor, etc. Only a thing to be aware of is need for parking. Not cheap, but several good options close by.
Highly recommended!
Reviewed on Jul 11, 2026
Top Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
22.75 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
25.65 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
Portland Harbor Hotel
468 Fore Street Portland ME
25.39 km from city center
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 ...
Portland Regency Hotel & Spa
20 Milk Street Portland ME
25.47 km from city center
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 ...
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
23.49 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
Comfort Inn South Portland Airport
90 Maine Mall Rd South Portland ME
20.43 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Fireside Inn & Suites Portland
81 Riverside St Portland ME
19 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
23.37 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Old Orchard Beach Inn
6 Portland Ave Old Orchard Beach ME
27.9 km from city center
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
25.07 km from city center
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Waves Oceanfront Resort
87 W Grand Ave Old Orchard Beach ME
28.66 km from city center
Book a stay at this beach hotel in Old Orchard Beach. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean ...
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
21.25 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality Inn & Suites South Portland
738 Main Street South Portland ME
23.55 km from city center
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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.
Wed, Aug 26 - Sat, Aug 29
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$149 Roundtrip, found 4 days ago
$149
Roundtrip
found 4 days ago
Sun, Aug 23 - Sat, Aug 29
LGA
LaGuardia
PWM
Portland Intl. Jetport
$157 Roundtrip, found 4 days ago
$157
Roundtrip
found 4 days ago
Sun, Aug 23 - Sat, Aug 29
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$157 Roundtrip, found 4 days ago
$157
Roundtrip
found 4 days ago
Tue, Aug 4 - Thu, Aug 13
LGA
LaGuardia
PWM
Portland Intl. Jetport
$181 Roundtrip, found 4 days ago
$181
Roundtrip
found 4 days ago
Wed, Oct 7 - Wed, Oct 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$194 Roundtrip, found 5 days ago
$194
Roundtrip
found 5 days ago