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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.
Ramada by Wyndham Saco/Old Orchard Beach Area

Ramada by Wyndham Saco/Old Orchard Beach Area

2.5 out of 5
Price was $886, price is now $678 per person
$678
per person
Jul 8 - Jul 11
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)
Book a stay at this business-friendly hotel in Saco. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Orchard Beach and Saco Museum are located nearby.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,249, price is now $883 per person
$883
per person
Jun 18 - Jun 21
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this 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 Kennebunkport Village Green are located nearby.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,365, price is now $966 per person
$966
per person
Jul 8 - Jul 11
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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 Victoria Mansion and Cross Insurance Arena are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $2,141, price is now $1,539 per person
$1,539
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $1,627, price is now $1,268 per person
$1,268
per person
Jun 11 - Jun 14
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Fire Museum 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 $1,712, price is now $1,335 per person
$1,335
per person
May 22 - May 26
found 19 hours 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 Thompson's Point and N.W. Barrett Gallery are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $1,452, price is now $1,151 per person
$1,151
per person
Jun 22 - 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 Thompson's Point and Cross Insurance Arena are located nearby.
Grasshopper Inn

Grasshopper Inn

4 out of 5
Save 100% on your flight
Price was $1,202, price is now $961 per person
$961
per person
Jun 18 - Jun 21
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Ramada by Wyndham Saco/Old Orchard Beach Area

Ramada by Wyndham Saco/Old Orchard Beach Area

2.5 out of 5
Price was $886, price is now $678 per person
$678
per person
Jul 8 - Jul 11
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
Price was $1,249, price is now $883 per person
$883
per person
Jun 18 - Jun 21
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,365, price is now $966 per person
$966
per person
Jul 8 - Jul 11
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $2,141, price is now $1,539 per person
$1,539
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)

Windham Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Freeport Hotel, an Ascend Collection Hotel

The Freeport Hotel, an Ascend Collection Hotel

2 out of 5
Price was $1,060, price is now $890 per person
$890
per person
May 30 - Jun 6
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Price was $1,743, price is now $1,419 per person
$1,419
per person
May 30 - Jun 6
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Nicholson Inn

The Nicholson Inn

3 out of 5
Price was $1,506, price is now $1,270 per person
$1,270
per person
May 30 - Jun 6
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Ocean Gate Inn

Ocean Gate Inn

3 out of 5
Price was $1,710, price is now $1,449 per person
$1,449
per person
May 30 - Jun 6
found 8 hours 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, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jun 16 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Jun 17, priced at $157 found 1 day ago
Breeze Airways
Fri, May 29 - Wed, Jun 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$177 Roundtrip, found 7 hours ago
$177
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Fri, May 29 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $177 found 7 hours ago
American Airlines
Tue, May 12 - Wed, May 13
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$202 Roundtrip, found 5 hours ago
$202
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Tue, May 12 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, May 13, priced at $202 found 5 hours ago
Delta
Sun, Apr 19 - Thu, Apr 30
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$262 Roundtrip, found 5 hours ago
$262
Roundtrip
found 5 hours ago
Select Delta flight, departing Sun, Apr 19 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Apr 30, priced at $262 found 5 hours ago