Windham Vacation Packages 2026 from $844

Windham flight + hotel vacation packages

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

Ogunquit River Inn & Suites

$844

per person

Jul 15 - Jul 18

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

Meadowmere Resort

Save 100% on your flight

$981

per person

Jul 15 - Jul 18

found 1 day ago

Roundtrip flight included

Denver (DEN) to Portland (PWM)

This smoke-free hotel features 2 hot tubs, an indoor pool, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.

The Weldon Hotel

Downtown Portland

Save 100% on your flight

$1,929

per person

Jul 29 - Aug 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

A 24-hour gym, self parking, and a virtual front desk are featured at this aparthotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Free WiFi in public areas is also provided.

Cliff House Maine

Bald Head

Save 100% on your flight

$1,593

per person

Jul 15 - Jul 18

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

Portland Harbor Hotel

Downtown Portland

$1,573

per person

Jul 29 - Aug 2

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.

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

$98 nightly

$109 total

May 10 - May 11

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

$228 nightly

$253 total

May 10 - May 11

Total with taxes and fees

Portland Regency Hotel & Spa

20 Milk Street Portland ME

$154 nightly

$170 total

May 10 - May 11

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.

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Free Cancellation

$177 nightly

$196 total

May 25 - May 26

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 and free WiFi in public areas. Self parking and a safe deposit box are also offered on site.

HomeAwhile

205 Southborough Drive Scarborough ME

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$136 total

May 31 - Jun 1

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME

Free Cancellation

$134 nightly

$148 total

May 10 - May 11

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.

Pool

Free airport shuttle

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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 $844. 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.