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Windham Vacation Packages

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Windham Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $707, price is now $502 per person
$502
per person
May 28 - May 31
found 17 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,649, price is now $1,119 per person
$1,119
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Fort Preble are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,951, price is now $1,351 per person
$1,351
per person
May 28 - May 31
found 17 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Book a stay at this 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 Perkins Cove and Marginal Way are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,779, price is now $1,295 per person
$1,295
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $1,912, price is now $1,419 per person
$1,419
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip 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 Maine Mall and Cathedral of the Immaculate Conception are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $3,152, price is now $2,348 per person
$2,348
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,932, price is now $1,499 per person
$1,499
per person
Jun 21 - Jun 26
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 concierge services. Popular attractions Maine Mall and Victoria Mansion are located nearby.
Grasshopper Inn

Grasshopper Inn

4 out of 5
Price was $1,230, price is now $956 per person
$956
per person
Jun 5 - Jun 8
found 7 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Stay at this inn in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ogunquit Beach and Marginal Way are located nearby.

Windham Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $707, price is now $502 per person
$502
per person
May 28 - May 31
found 17 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,951, price is now $1,351 per person
$1,351
per person
May 28 - May 31
found 17 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,908, price is now $1,404 per person
$1,404
per person
Jun 26 - Jun 29
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,665, price is now $1,252 per person
$1,252
per person
Jun 26 - Jun 29
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)

Windham Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was $1,456, price is now $1,036 per person
$1,036
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,649, price is now $1,119 per person
$1,119
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,779, price is now $1,295 per person
$1,295
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,912, price is now $1,419 per person
$1,419
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

United
Tue, Jun 16 - Wed, Jun 17
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$157 Roundtrip, just found
$157
Roundtrip
just found
Select United flight, departing Tue, Jun 16 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Jun 17, priced at $157 just found
Breeze Airways
Fri, May 29 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 1 hour ago
$185
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, May 29 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $185 found 1 hour ago
American Airlines
Mon, May 18 - Wed, May 27
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$223 Roundtrip, found 1 day ago
$223
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, May 18 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, May 27, priced at $223 found 1 day ago
American Airlines
Wed, May 27 - Tue, Jun 9
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$264 Roundtrip, found 2 hours ago
$264
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, May 27 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Tue, Jun 9, priced at $264 found 2 hours ago