Deals on vacations and trips to Windham

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Windham flight + hotel vacation packages

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

Chebeague Island Inn

4 out of 5
Price was $1,029, price is now $768 per person
$768
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate perks like free WiFi and a free ferry terminal shuttle. A garden, a lobby fireplace, and a picnic area are also on offer.
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,002, price is now $1,341 per person
$1,341
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
Free WiFi in public areas is available at this aparthotel. Take advantage of the self parking.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,628, price is now $1,171 per person
$1,171
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,153, price is now $830 per person
$830
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,511, price is now $1,168 per person
$1,168
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.

Top Windham hotels deals

Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Free Cancellation
$93 nightly
The price is $101 total per night
$101 total
Sep 6 - Sep 7
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.
Pool
Breakfast included
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
$131 nightly
The price is $145 total per night
$145 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.
Pool
Hot Tub
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Free Cancellation
$96 nightly
The price is $104 total per night
$104 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.
Breakfast included
Pet friendly
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$355 nightly
The price is $393 total per night
$393 total
Aug 30 - Aug 31
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.
Hot Tub
Spa
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $119 total per night
$119 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Pool
Hot Tub
Waves Oceanfront Resort

Waves Oceanfront Resort

3 out of 5
87 W Grand Ave Old Orchard Beach ME
$190 nightly
The price is $207 total per night
$207 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A coffee shop, a lobby fireplace, and a picnic area are also on offer.
Pool
Hot Tub
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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.

Stay near popular Windham attractions

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.
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Frequently asked questions

How much are vacation packages to Windham?
You can score a fantastic flight and hotel bundle for as low as $768. 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.

Photos of local treasures

Browse Windham vacation photos for more inspiration

A lake surrounded by houses and trees with autumn foliage.
A white church with a steeple and red accents, surrounded by autumn trees.
A residential street with houses, autumn foliage, and parked cars.
A welcome sign to Windham, founded 1737, with a logo for Windham Eagles.
A road with directional signs for Route 202 East and Route 4 North, surrounded by autumn foliage.

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