Search Deals onWindham Vacation Packages
Windham Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Price was $853, price is now $671 per person
$671
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Cliff House Maine
Save 100% on your flight
Price was $1,956, price is now $1,439 per person
$1,439
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The McKernan Inn
Price was $1,425, price is now $1,082 per person
$1,082
per person
Nov 15 - Nov 21
found 2 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
The Docent's Collection
Price was $974, price is now $749 per person
$749
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Inn By The Sea
Price was $1,049, price is now $815 per person
$815
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Canopy by Hilton Portland Waterfront
Price was $1,507, price is now $1,207 per person
$1,207
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this 4-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Kennebunkport Captains Collection
Price was $906, price is now $727 per person
$727
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 Wells Beach are located nearby.
Blind Tiger Portland - Danforth Street.
Price was $1,005, price is now $811 per person
$811
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. 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.
Fri, Oct 17 - Wed, Oct 22
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$107 Roundtrip, found 4 days ago
$107
Roundtrip
found 4 days ago
Tue, Sep 16 - Tue, Sep 30
LGA
LaGuardia
PWM
Portland Intl. Jetport
$109 Roundtrip, found 3 days ago
$109
Roundtrip
found 3 days ago
Mon, Sep 15 - Tue, Sep 23
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$161 Roundtrip, found 6 days ago
$161
Roundtrip
found 6 days ago
Wed, Sep 10 - Wed, Sep 17
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
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