Search Deals onWindham Vacation Packages
Windham Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Grand Beach Inn
per person
May 24 - May 26
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
Stay at this 3-star hotel in Old Orchard Beach. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Old Orchard Beach Pier and Old Orchard Beach are located nearby.
River View Resort
Save 100% on your flight
per person
Jun 28 - Jul 4
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
Waldo Emerson Inn
Save 100% on your flight
per person
Jun 28 - Jul 4
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this 3-star B&B in Kennebunk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. Popular attractions Wedding Cake House and Kennebunk Dog Park are located nearby.
Portland Harbor Hotel
Save 100% on your flight
per person
Jun 28 - Jul 4
found 3 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Casco Bay Inn
per person
May 24 - May 26
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Eartha and Clay Play are located nearby.
The Freeport Hotel, Ascend Hotel Collection
per person
May 24 - May 26
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
Book a stay at this business-friendly motel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bradbury Mountain State Park and Wilbur's of Maine Chocolate Confections are located nearby.
Fairfield by Marriott Inn & Suites Portland Maine Airport
per person
May 24 - May 26
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
Book a stay at this business-friendly hotel in Scarborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
Fireside Inn & Suites Portland
per person
May 24 - May 26
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Portland (PWM)
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 rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Windham Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Windham 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.
Thu, May 1 - Mon, May 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$101 Roundtrip, found 3 days ago
$101
Roundtrip
found 3 days ago
Wed, Aug 20 - Wed, Aug 27
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
Sat, Jul 5 - Tue, Jul 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Wed, May 14 - Mon, May 19
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
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