Search Deals onChebeague Island Vacation Packages
Chebeague Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Weldon Hotel
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 4.5-star luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point and Maine Mall are located nearby.
Cliff House Maine
Save 100% on your flight
per person
Oct 9 - Oct 12
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 4.5-star 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 Ogunquit Beach and Perkins Cove are located nearby.
Portland Harbor Hotel
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
The Docent's Collection
Save 100% on your flight
per person
Sep 29 - Oct 2
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 3.5-star hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Thompson's Point and Maine Mall are located nearby.
The McKernan Inn
Save 100% on your flight
per person
Sep 29 - Oct 2
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 3-star beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Maine Mall are located nearby.
Kennebunkport Captains Collection
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 4.5-star 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 Goose Rocks Beach are located nearby.
Inn By The Sea
Save 100% on your flight
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PWM)
Stay at this 4-star 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.
Chebeague Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chebeague Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$100 Roundtrip, found 4 days ago
$100
Roundtrip
found 4 days ago
Sun, Oct 12 - Thu, Oct 16
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Tue, Sep 16 - Tue, Sep 30
LGA
LaGuardia
PWM
Portland Intl. Jetport
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Tue, Sep 2 - Tue, Sep 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$119 Roundtrip, found 4 days ago
$119
Roundtrip
found 4 days ago
Discover Other Travel Deals
- Old Orchard Beach Pier Vacations
- Thompson's Point Vacations
- Maine Mall Vacations
- LL Bean Flagship Store Vacations
- State Theatre Vacations
- Bowdoin College Vacations
- Portland Head Light Vacations
- Higgins Beach Vacations
- Maine Medical Center Vacations
- Casco Bay Lines Ferry Terminal Vacations
- Cross Insurance Arena Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in Chebeague Island
- Car rentals in Portland
- Car rentals in Old Orchard Beach
- Car rentals in South Portland
- Car rentals in Scarborough
- Car rentals in Freeport
- Car rentals in Saco
- Car rentals in Brunswick
- Car rentals in Cape Elizabeth
- Car rentals in Standish
- Car rentals in Raymond
- Car rentals in Bath
- Car rentals in Phippsburg