Search Deals onWindham Vacation Packages
Windham Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove
Price was $953, price is now $688 per person
$688
per person
Sep 24 - Sep 27
found 24 hours ago
Roundtrip non-stop flight included
Columbus (CMH) 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
Save 100% on your flight
Price was $1,919, price is now $1,229 per person
$1,229
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Casco Bay Lines Ferry Terminal 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 Docent's Collection at 121 Middle Street
Save 100% on your flight
Price was $1,366, price is now $987 per person
$987
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Beautiful place to stay
Reviewed on Jul 15, 2026
The Meadowmere Resort
Price was $1,274, price is now $953 per person
$953
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Marginal Way and Ogunquit Beach are located nearby.
Staff was very helpful, room was clean, and great location! Would definitely stay there again
Reviewed on Jul 14, 2026
Blind Tiger Portland - Danforth Street.
Price was $1,982, price is now $1,499 per person
$1,499
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Cross Insurance Arena are located nearby.
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.
Reviewed on Jun 26, 2026
The Weldon Hotel
Save 100% on your flight
Price was $1,657, price is now $1,259 per person
$1,259
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
Ogunquit River Inn & Suites
Price was $1,058, price is now $807 per person
$807
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Portland (PWM)
Book a stay at this business-friendly hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
Room was very comfortable. A/C worked too well! Easy check in. Would stay here again definitely. Worth the extra cost for balcony room.
Reviewed on Jul 16, 2026
The Docent's Collection at 178 Middle Street
Price was $1,464, price is now $1,138 per person
$1,138
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
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.
Wed, Sep 16 - Wed, Sep 23
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 6 days ago
$189
Roundtrip
found 6 days ago
Tue, Sep 8 - Sat, Sep 12
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$196 Roundtrip, found 12 hours ago
$196
Roundtrip
found 12 hours ago
Wed, Aug 5 - Sat, Aug 22
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$208 Roundtrip, found 22 hours ago
$208
Roundtrip
found 22 hours ago
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