Bay View Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Bay View Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was $932, price is now $676 per person
$676
per person
Apr 18 - Apr 24
found 1 day ago
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.
The Docent's Collection at 121 Middle Street
Downtown Portland
Save 100% on your flight
Price was $1,059, price is now $735 per person
$735
per person
Apr 18 - Apr 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Mall and Cathedral of the Immaculate Conception are located nearby.
84 Main
Save 100% on your flight
Price was $1,007, price is now $710 per person
$710
per person
Apr 18 - Apr 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Kennebunk Free Library and Brick Store Museum are located nearby.
Inn By The Sea
Save 100% on your flight
Price was $1,336, price is now $1,048 per person
$1,048
per person
Apr 18 - Apr 24
found 1 day 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.
Portland Regency Hotel & Spa
Downtown Portland
Price was $929, price is now $742 per person
$742
per person
Apr 18 - Apr 24
found 1 day 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.
The Press Hotel, Marriott Autograph Collection
Downtown Portland
Price was $1,090, price is now $876 per person
$876
per person
Apr 18 - Apr 24
found 1 day ago
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
The Westin Portland Harborview
157 High St Portland ME
21.27 km from Bay View
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
20.52 km from Bay View
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 ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
21.3 km from Bay View
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 ...
Portland Harbor Hotel
468 Fore Street Portland ME
21.68 km from Bay View
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
21.97 km from Bay View
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 ...
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
22.52 km from Bay View
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 ...
Old Orchard Beach Inn
6 Portland Ave Old Orchard Beach ME
3.68 km from Bay View
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. ...
Hyatt Place Portland Downtown - Old Port Square
433 Fore St Portland ME
21.75 km from Bay View
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Hampton Inn Portland Downtown - Waterfront
209 Fore St Portland ME
22.22 km from Bay View
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
20.75 km from Bay View
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 ...
Aloft Portland Downtown Waterfront ME
379 Commercial Street Portland ME
21.22 km from Bay View
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 bar and ...
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St Portland ME
22.12 km from Bay View
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Embassy Suites by Hilton Portland Maine
1050 Westbrook Street Portland ME
19.4 km from Bay View
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
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.
Mon, May 25 - Mon, Jun 1
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$177 Roundtrip, found 13 hours ago
$177
Roundtrip
found 13 hours ago
Mon, May 25 - Fri, May 29
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$177 Roundtrip, found 23 hours ago
$177
Roundtrip
found 23 hours ago
Mon, May 4 - Wed, May 13
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$177 Roundtrip, found 5 hours ago
$177
Roundtrip
found 5 hours ago
Tue, Sep 8 - Fri, Sep 11
LGA
LaGuardia
PWM
Portland Intl. Jetport
$202 Roundtrip, just found
$202
Roundtrip
just found
Sat, Jun 6 - Sat, Jun 13
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$221 Roundtrip, found 2 hours ago
$221
Roundtrip
found 2 hours ago