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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.
The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
Price was $487, price is now $405 per person
$405
per person
Apr 10 - Apr 12
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this beach hotel in Wolfeboro. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Lake Winnipesaukee and Hampshire Pewter Co. are located nearby.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Price was $915, price is now $726 per person
$726
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Price was $765, price is now $626 per person
$626
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Cross Insurance Arena and Fore Street Gallery are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $901, price is now $746 per person
$746
per person
Apr 10 - Apr 12
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Price was $780, price is now $647 per person
$647
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Charles Q. Clapp House are located nearby.
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $767, price is now $641 per person
$641
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fort Preble and Portland Harbor Museum are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $846, price is now $712 per person
$712
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $707, price is now $615 per person
$615
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.

Windham Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $765, price is now $626 per person
$626
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $915, price is now $726 per person
$726
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,083, price is now $864 per person
$864
per person
May 16 - May 19
found 21 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,013, price is now $811 per person
$811
per person
May 16 - May 19
found 21 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)

Windham Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $939, price is now $700 per person
$700
per person
Apr 16 - Apr 21
just found
Roundtrip non-stop flight included
Louisville (SDF) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $991, price is now $704 per person
$704
per person
Apr 16 - Apr 21
just found
Roundtrip non-stop flight included
Louisville (SDF) to Portland (PWM)
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $989, price is now $716 per person
$716
per person
Apr 16 - Apr 21
just found
Roundtrip non-stop flight included
Louisville (SDF) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,230, price is now $923 per person
$923
per person
Apr 16 - Apr 21
just found
Roundtrip non-stop flight included
Louisville (SDF) to Portland (PWM)

Top Flight Deals

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

American Airlines
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, just found
$183
Roundtrip
just found
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $183 just found
JetBlue Airways
Wed, Apr 15 - Mon, Apr 27
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 23 hours ago
$189
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Wed, Apr 15 from Tampa Intl. to Portland Intl. Jetport, returning Mon, Apr 27, priced at $189 found 23 hours ago
Delta
Mon, Mar 9 - Sat, Mar 14
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$213 Roundtrip, found 5 days ago
$213
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Mar 9 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Mar 14, priced at $213 found 5 days ago
JetBlue Airways
Tue, Jun 2 - Wed, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Jun 2 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $227 found 1 day ago