Windham Vacation Packages 2026 from $1,104

Windham flight + hotel vacation packages

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

Portland Harbor Hotel

Downtown Portland

$1,104

per person

Sep 17 - Sep 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

Ogunquit River Inn & Suites

Moody

Save 100% on your flight

$1,194

per person

Jul 29 - Aug 4

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a seasonal outdoor pool on site, and a terrace and a garden are also provided.

The Meadowmere Resort

Save 100% on your flight

$1,347

per person

Aug 2 - Aug 7

found 1 day ago

Roundtrip non-stop flight included

Raleigh (RDU) to Portland (PWM)

2 hot tubs, an indoor pool, and a gym are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. There's a restaurant and a bar/lounge for dining and drinks, and also a sauna on site.

Cliff House Maine

Bald Head

Save 100% on your flight

$2,100

per person

Aug 2 - Aug 7

found 1 day ago

Roundtrip non-stop flight included

Raleigh (RDU) to Portland (PWM)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.

Newagen Seaside Inn

Save 100% on your flight

$1,216

per person

Aug 2 - Aug 7

found 1 day ago

Roundtrip non-stop flight included

Raleigh (RDU) to Portland (PWM)

This hotel features 2 outdoor tennis courts, an outdoor pool, and a restaurant. There's fun for all ages with a bowling alley and a playground, and families will appreciate the picnic area. Enjoy the gym and perks like free self parking and free WiFi.

Top Windham hotels deals

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

340 Park Ave Portland ME

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$154 total

Jun 29 - Jun 30

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the free on-the-go breakfast each morning.

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$322 nightly

$356 total

Jun 28 - Jun 29

Total with taxes and fees

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Free Cancellation

Reserve now, pay when you stay

$286 nightly

$317 total

Jun 28 - Jun 29

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A safe deposit box is provided and the front desk is staffed around-the-clock.

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Free Cancellation

$99 nightly

$108 total

Jun 29 - Jun 30

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.

Ramada Plaza by Wyndham Portland

155 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$142 total

Jun 29 - Jun 30

Total with taxes and fees

This hotel features 2 restaurants, 2 hot tubs, and an indoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Portland Regency Hotel & Spa

20 Milk Street Portland ME

$229 nightly

$254 total

Jun 28 - Jun 29

Total with taxes and fees

A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Seacoast Adventure

Bring the family to Seacoast Adventure and enjoy some excitement at this amusement park in Windham. Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.

beach near Boathouse Beach Lane

Why not spend a lazy afternoon at beach near Boathouse Beach Lane during your trip to Windham? Stroll along this family-friendly area's lakeside, or simply enjoy its restaurants.

Frequently asked questions

How much are vacation packages to Windham?

You can score a fantastic flight and hotel bundle for as low as $1,104. With one of our Travelocity vacation packages, an escape to Windham has never looked more irresistible! Save some time and money and get an early start with packing your suitcases.

How long should my Windham vacation be?

Many travelers pack their suitcase and explore the sights of Windham for about 2 nights. That's a good starting point, but don't be restricted by it. Whether you only stay a couple of nights to see the big attractions or stick around to experience this place like a local, an unforgettable journey awaits.

Where can I get the best vacation package deals for Windham?

You'll find a fantastic range of Windham package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties worldwide, putting together your dream escape will be a breeze.

Why should I book my Windham vacation package with Travelocity?

From our 24/7 customer support to our range of terrific destinations, we are committed to giving you the most unforgettable vacation. All you have to do is click and book — our Price Match Guarantee will ensure you score the cheapest price.

Can I save money on my Windham car rental if I book it with hotels and flights?

Bundling your flight, hotel and car into a Windham vacation package is an excellent way to land the best prices. Plus, having your own wheels gives you freedom to get to all those big-name sights you want to explore. Sitting 100 mi away from Windham, Fenway Park is one place that should be on your itinerary. Load up the car and make a day trip of it.

Which airport is best for Windham?

Portland Intl. Jetport Airport (PWM), 9 mi southeast of the city center, is where many people begin their adventures in Windham. But Augusta State Airport (AUG) (50 mi away from central Windham) could be the more convenient option for you.

What is there to do in Windham?

You'll feel a particular magic in the air as you roam the streets of Windham. Maine Wildlife Park and Seacoast Adventure are just two attractions that make this city so popular, so put them at the top of your travel itinerary.

Where should I stay when visiting Windham?

Many visitors check in to the Microtel Inn & Suites By Wyndham Windham. It's the perfect base for your Windham escape.