Windham Vacation Packages 2025 from $640

Windham flight + hotel vacation packages

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

Best Western Freeport Inn

per person

Aug 31 - Sep 7

found 12 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. There's a seasonal outdoor pool on site, and a 24-hour front desk and express check-out are also provided.

Admiral Peary Inn

Save 100% on your flight

per person

Jul 12 - Jul 19

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A coffee shop, a garden, and a snack bar/deli are also on offer.

The Docent's Collection

Downtown Portland

Save 100% on your flight

per person

Aug 31 - Sep 7

found 12 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to Portland (PWM)

This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out and dry cleaning are also provided.

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

per person

Aug 31 - Sep 7

found 12 hours ago

Roundtrip non-stop flight included

Columbus (CMH) 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.

Nautical Mile

Save 100% on your flight

per person

Sep 4 - Sep 8

found 1 day ago

Roundtrip flight included

Columbus (CMH) to Portland (PWM)

A seasonal outdoor pool is featured at this aparthotel, along with free self parking. A picnic area and a computer station are also provided.

Top Windham hotels deals

La Quinta Inn & Suites by Wyndham Portland

340 Park Ave, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and a free airport shuttle. Business travelers can take advantage of the business center. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

The Westin Portland Harborview

157 High St, Portland, ME

Free Cancellation

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A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Spa

Pet friendly

Inn at St John Portland In-Town

939 Congress St, Portland, ME

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This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A lobby fireplace, a computer station, and luggage storage are also on offer.

Breakfast included

Pet friendly

Canopy by Hilton Portland Waterfront

9 Center Street, Portland, ME

Free Cancellation

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This hotel features 2 restaurants and a 24-hour gym. WiFi in public areas is free. Valet parking, a lobby fireplace, and a communal living room are also offered.

Pet friendly

Free WiFi

Portland Harbor Hotel

468 Fore Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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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.

Pet friendly

Free WiFi

Portland Regency Hotel & Spa

20 Milk Street, Portland, ME

Free Cancellation

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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.

Hot Tub

Spa

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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

Maine Wildlife Park

4.5/5(6 reviews)

Meet the animals who live at Maine Wildlife Park during your trip to Windham. While in this family-friendly area, you can savor the top-notch restaurants.

Seacoast Adventure

5/5(4 reviews)

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.

Mercy Primary Care

Though Mercy Primary Care might be what brings you to town, perhaps you'll have a chance to explore more of Windham while you are here.

Frequently asked questions

How much are vacation packages to Windham?

You can score a fantastic flight and hotel bundle for as low as $640. 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.