---
title: "Windham Vacation Packages 2026 from $782 | Expedia"
description: "Bundle Windham flight + hotel & save up to 100% off your flight with Expedia. Filter packages by price, amenities & location. FREE cancellation on select hotels."
canonical: "https://www.expedia.com/Windham.d10053.Destination-Travel-Guides"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-14T15:47:08Z
---

# Windham Vacations from $774
![A white church with a steeple and red accents, surrounded by autumn trees.](https://images.trvl-media.com/place/10053/e35578b1-da57-445e-877f-214e815ca305.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

Book a Hotel + Flight or Car together to unlock savings

## Your Windham Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Windham vacation package. Book a hotel in Parkside, which is good for festivals, markets and walking. If your trip to Windham includes a little sightseeing, don't miss well-known attractions like [Maine Wildlife Park](https://www.expedia.com/Maine-Wildlife-Park-Windham.d553248621532667988.Vacation-Attraction), [Riverside Municipal Golf Course](https://www.expedia.com/Riverside-Municipal-Golf-Course-Portland.d6327744.Vacation-Attraction) and [MAGAN Trailhead](https://www.expedia.com/MAGAN-Trailhead-Portland.d641530092651474944.Vacation-Attraction). Check out Expedia's wide range of travel options and begin planning your perfect vacation to Windham today.

## The Latest Windham Vacation Packages

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

Trip length

3 nights4 nights5 nights6-7 nights

Stars

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- ![A two-story house with a balcony, a front porch, and a well-lit garden area.](https://images.trvl-media.com/lodging/72000000/71810000/71807100/71807037/429c0f3c.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A covered outdoor area with wicker furniture, a glass table, and a view of the ocean.](https://images.trvl-media.com/lodging/72000000/71810000/71807100/71807037/6e64078d.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 21 - Jan 24**

### [Cape Arundel Inn and Resort + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-21/2027-01-24/?FromAirport=ATL&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=71807037&dealMarker=&paandie=true&cabinClass=e)
Kennebunkport
3 nights

**9.6/10** \- Exceptional (57 reviews)
"A special hotel. Beautiful setting, unique one-of-kind inn. So very Maine coastal. Staff could not have been more appropriately available, helpful, kind. Lovely experience all around."
Reviewed October 26, 2026
Roundtrip • Atlanta (ATL) - Portland (PWM)
ATL - BOS • Nonstop BOS - ATL • Nonstop
[~~$867~~](https://www.expedia.com/)

**$774**
per traveler
found 1 day ago
- ![A spacious living room with a fireplace, white walls, and a large window.](https://images.trvl-media.com/lodging/14000000/13280000/13279300/13279259/c4a328d8.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A room with a white sofa, a small round table, and a lamp.](https://images.trvl-media.com/lodging/14000000/13280000/13279300/13279259/4674d8a8.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 31 - Jan 5**

### [Kennebunkport Captains Collection + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-31/2027-01-05/?FromAirport=DFW&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13279259&dealMarker=&paandie=true&cabinClass=e)
Kennebunkport
5 nights

**9.6/10** \- Exceptional (774 reviews)
"Amazing place for our Mini Moon! Would definitely recommend"
Reviewed November 13, 2026
Roundtrip • Dallas (DFW) - Portland (PWM)
DAL - BOS • Nonstop BOS - DFW • 1 stop
[~~$1,486~~](https://www.expedia.com/)

**$1,202**
per traveler
found 1 day ago
- ![A fire pit surrounded by wicker chairs in a garden setting.](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A dining area with round tables and chairs, a view of the garden through large windows, and a cozy atmosphere.](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/b69d3811.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 22 - Dec 28**

### [Portland Harbor Hotel + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-22/2026-12-28/?FromAirport=DFW&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=898621&dealMarker=&paandie=true&cabinClass=e)
Downtown Portland
6 nights

**9.2/10** \- Wonderful (1,866 reviews)
"Old hotel recently updated. Great location in Old Port in walking distance of restaurants and shop. Very helpful staff. Easy valet parking. They charge a resort fee but you get it back as credit to use for breakfast or at the bar. Great outdoor patio area with gas fire pit. Great vibe for adult travelers."
Reviewed November 14, 2026
Roundtrip • Dallas (DFW) - Portland (PWM)
DFW - PWM • 1 stop PWM - DFW • 1 stop
[~~$1,141~~](https://www.expedia.com/)

**$965**
per traveler
found 1 day ago
- ![A resort with a pool, lounge chairs, umbrellas, and a view of the ocean.](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/50b1cace.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A table set for two with a candle, glasses, and a menu, overlooking a coastal view with a sunset.](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/b45f5c6c.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 21 - Jan 24**

### [Cliff House Maine + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-21/2027-01-24/?FromAirport=ATL&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3981160&dealMarker=&paandie=true&cabinClass=e)
Bald Head
3 nights

**9.4/10** \- Exceptional (1,001 reviews)
Roundtrip • Atlanta (ATL) - Portland (PWM)
ATL - BOS • Nonstop BOS - ATL • Nonstop
[~~$1,210~~](https://www.expedia.com/)

**$1,048**
per traveler
found 1 day ago
- ![A spacious living room with a large dining table, comfortable seating, and large windows offering views of the city.](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/368089b1.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A modern living room with a sofa, coffee table, and chairs. There is a kitchen area with cabinets and a refrigerator.](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/0e60276b.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 19 - Dec 21**

### [The Docent's Collection at 121 Middle Street + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-19/2026-12-21/?FromAirport=BNA&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=38770068&dealMarker=&paandie=true&cabinClass=e)
Downtown Portland
2 nights

**9.6/10** \- Exceptional (431 reviews)
"The property was excellent. We stayed in a 1 bedroom loft and it was great. Nice sitting area, fully equipped kitchen, beautiful bathroom and nice size bedroom. It was quiet and comfy, and also walking distance to great restaurants. Highly recommend."
Reviewed November 12, 2026
Roundtrip • Nashville (BNA) - Portland (PWM)
BNA - PWM • 1 stop PWM - BNA • 2 stops
[~~$881~~](https://www.expedia.com/)

**$782**
per traveler
found 3 hours ago

## Where to stay in and around Windham

Windham, Maine, offers a charming blend of outdoor adventures and scenic beauty, perfect for families and romantic getaways. Nearby, explore the friendly atmosphere of Brunswick and discover cozy accommodations. Don’t miss the enchanting Houmas House or the allure of nearby sleepy towns, ideal for a peaceful retreat.

- [Portland](#)
- [Westbrook](#)
- [Gorham](#)
- [North Windham](#)
- [Little Falls-South Windham](#)

![A lighthouse and houses on a rocky coastline with the ocean in the background.](https://images.trvl-media.com/place/181420/c0dd3185-7ed8-4ae8-9720-e05e2773916c.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for Portland](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=181420)

### Portland

Discover Portland, a vibrant city that appeals to family and adventure travelers seeking a memorable trip. With its mix of outdoor activities and scenic spots, visitors can enjoy the lively atmosphere at the Cross Insurance Arena, explore the artistic treasures at the Portland Museum of Art, or unwind at nearby beaches and lakes. Located about 10 miles by car from Windham, Portland offers a perfect base for your getaway, making it an excellent choice for a hotel stay.

[See properties](https://www.expedia.com/Hotel-Search?regionId=181420)

![A frozen river with a bridge crossing over it, surrounded by buildings and parked cars.](https://images.trvl-media.com/place/56049/bd12d6d6-239c-4842-819c-8dcb28edc701.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for Westbrook](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=56049)

### Westbrook

Experience the charm of Westbrook, an excellent hub for outdoor enthusiasts and families looking for a memorable weekend getaway. This vibrant city offers easy access to scenic lakes, family-friendly beaches, and cultural gems like the Portland Museum of Art and the University of New England. With a short drive of about 6 miles from Windham, Westbrook provides a perfect blend of relaxation and adventure, making it a smart choice for your next vacation stay.

[See properties](https://www.expedia.com/Hotel-Search?regionId=56049)

![A forest with autumn foliage, a mountain range, and a cloudy sky.](https://images.trvl-media.com/place/6347753/0e28cb3b-2b23-4dec-b3fb-c24c456b894a.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for Gorham](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=6347753)

### Gorham

Make your vacation planning effortless by staying in Gorham, a haven for outdoor enthusiasts and families eager to explore the beautiful scenery. With attractions like the historic University of New England and the vibrant Portland Museum of Art nearby, there’s plenty to see and do. Gorham is located about 6 miles by car from Windham, making it an easy drive for a weekend getaway. Choose Gorham for a well-rounded experience that combines adventure and relaxation.

[See properties](https://www.expedia.com/Hotel-Search?regionId=6347753)

[View properties in map for North Windham](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=553248634999118067)

### North Windham

Ideally situated for outdoor enthusiasts and families, North Windham serves as a gateway to stunning attractions like Sebago Lake and the scenic Raymond Cape. Visitors can enjoy recreational areas, educational sites, and shopping at the local mall center, making it perfect for a balanced getaway. Located within Windham, North Windham offers easy access to these experiences year-round. Choose North Windham for a memorable stay where adventure and relaxation meet in a beautiful setting.

[See properties](https://www.expedia.com/Hotel-Search?regionId=553248634999118067)

[View properties in map for Little Falls-South Windham](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=553248634999088397)

### Little Falls-South Windham

Travelers visiting Windham, Maine, will find Little Falls-South Windham to be the ideal base for their vacation, featuring a charming village atmosphere that appeals to outdoor enthusiasts, families, and couples alike. With access to beautiful lakes and scenic beaches, along with local attractions like the Cross Insurance Arena and the Portland Museum of Art, visitors can enjoy a variety of activities year-round. Nestled in Windham, Little Falls-South Windham offers a smart choice for your stay, blending relaxation with adventure.

[See properties](https://www.expedia.com/Hotel-Search?regionId=553248634999088397)

## Discover the most popular places to visit in Windham

### 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.

[See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=1014296411059335168)

### What to do in Windham

![Phantoms, Penance, and Poltergeists: Portland, ME Ghost Tour](https://mediaim.expedia.com/localexpert/54042070/2d079b42-a046-4753-9f93-f82fb262f3af.jpg?impolicy=resizecrop&rw=1005&rh=565)

#### [Phantoms, Penance, and Poltergeists: Portland, ME Ghost Tour](https://www.expedia.com/things-to-do/a.a54042070.activity-details?rid=10053)

$32

per adult

0% of travelers recommend

![A Walk Through Time Tour in Portland](https://mediaim.expedia.com/localexpert/1010003/3a28b9b8-bffd-42f5-ac15-7e9eb3d96589.jpg?impolicy=resizecrop&rw=1005&rh=565)

#### [A Walk Through Time Tour in Portland](https://www.expedia.com/things-to-do/a.a1010003.activity-details?rid=10053)

$49

per adult

98% of travelers recommend

![Portland Self-Guided Driving Audio Tour](https://mediaim.expedia.com/localexpert/45719150/c5757d24-772a-4314-9a5b-385c37350ecc.jpg?impolicy=resizecrop&rw=1005&rh=565)

#### [Portland Smartphone Audio Tour: Self-Guided Drive](https://www.expedia.com/things-to-do/a.a45719150.activity-details?rid=10053)

$17

per traveler

100% of travelers recommend

[See all activities in Windham](https://www.expedia.com/things-to-do/search?rid=10053)

## Windham Hotel Deals

### [Dormir](https://www.expedia.com/Windham-Hotels-Dormir.h9312400.Hotel-Information)

![A bright room with large windows, two armchairs, a small table, and a chandelier.](https://images.trvl-media.com/lodging/10000000/9320000/9312400/9312400/eaaa6212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 965 Roosevelt Trail, Windham, ME, 04062, US
- Location: 7.3 mi from Windham
- Star rating: 3/5
- Guest rating: 9/10 (Wonderful, 1000 reviews)
- Price: $128 nightly, $139 total, Dec 15 - Dec 16, Total with taxes and fees

### [Hampton Inn & Suites Portland West](https://www.expedia.com/Portland-Hotels-Hampton-Inn-Suites-Portland-West.h38229978.Hotel-Information)

![A breakfast area with a sign that reads "HAPPY BREAKFAST STARTS HERE" and a coffee machine.](https://images.trvl-media.com/lodging/39000000/38230000/38230000/38229978/d6e0a0fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1210 Brighton Ave, Portland, ME, 04102, US
- Location: 6.7 mi from Windham
- Star rating: 2.5/5
- Guest rating: 8.8/10 (Excellent, 685 reviews)
- Price: $89 nightly, $99 total, Nov 21 - Nov 22, Total with taxes and fees
- Review: We had no issues with anything during our one night stay. Breakfast was excedllent. I will say that the location was noisy (traffic) if you're not used to that. Lots of shopping and food optionsnearby. Beds were comfy. Parking easy. Convenient location.

### [Ramada Plaza by Wyndham Portland](https://www.expedia.com/Portland-Hotels-Ramada-Plaza-By-Wyndham-Portland.h2908.Hotel-Information)

![A coffee shop interior with a counter, shelves with coffee products, and seating area.](https://images.trvl-media.com/lodging/1000000/10000/3000/2908/583cbf9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 155 Riverside St, Portland, ME, 04103, US
- Location: 6.4 mi from Windham
- Star rating: 3/5
- Guest rating: 8/10 (Very good, 1000 reviews)
- Price: $73 nightly, $81 total, Nov 18 - Nov 19, Total with taxes and fees

### [Embassy Suites by Hilton Portland Maine](https://www.expedia.com/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Maine.h14751.Hotel-Information)

![A spacious lobby with multiple seating areas, a fireplace, and large windows.](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/6b6e052e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1050 Westbrook Street, Portland, ME, 04102, US
- Location: 8.7 mi from Windham
- Star rating: 3.5/5
- Guest rating: 9.4/10 (Exceptional, 1202 reviews)
- Price: $106 nightly, $117 total, Dec 1 - Dec 2, Total with taxes and fees

### [Fireside Inn & Suites Portland](https://www.expedia.com/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information)

![An indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.](https://images.trvl-media.com/lodging/1000000/10000/9900/9842/2b589d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 81 Riverside St, Portland, ME, 04103, US
- Location: 6.5 mi from Windham
- Star rating: 3/5
- Guest rating: 8.2/10 (Very good, 1001 reviews)
- Price: $77 nightly, $85 total, Nov 22 - Nov 23, Total with taxes and fees
- Review: Older property, room was very clean, gym was clean and all equipment functional. Conveniently located for shopping and dining. Easy access to highway.

### [Aloft by Marriott Portland Downtown Waterfront ME](https://www.expedia.com/Portland-Hotels-Aloft-Portland.h68847370.Hotel-Information)

![A modern bar area with a bar counter, seating, and a view of the cityscape.](https://images.trvl-media.com/lodging/69000000/68850000/68847400/68847370/8a8afa7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 379 Commercial Street, Portland, ME, 04101, US
- Location: 10.2 mi from Windham
- Star rating: 3/5
- Guest rating: 9/10 (Wonderful, 1002 reviews)
- Price: $83 nightly, $92 total, Nov 22 - Nov 23, Total with taxes and fees
- Review: great location, friendly staff, clean, would stay again

### [Cambria Hotel Portland Downtown-Old Port](https://www.expedia.com/Portland-Hotels-Cambria-Hotel-Portland-Downtown-Old-Port.h77981687.Hotel-Information)

![A rooftop terrace with a modern outdoor seating area, a fire pit, and a view of the cityscape.](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/2540bb39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 25 HANCOCK STREET, Portland, ME, 04101, US
- Location: 10.1 mi from Windham
- Star rating: 3/5
- Guest rating: 9.2/10 (Wonderful, 1341 reviews)
- Price: $120 nightly, $133 total, Dec 6 - Dec 7, Total with taxes and fees

### [Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel](https://www.expedia.com/South-Portland-Hotels-Casco-Bay-Hotel.h1084959.Hotel-Information)

![A modern hotel lobby with a central seating area, a reception desk, and a kitchen in the background.](https://images.trvl-media.com/lodging/2000000/1090000/1085000/1084959/934ddba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 80 John Roberts Rd., South Portland, ME, 04106, US
- Location: 9.5 mi from Windham
- Star rating: 3.5/5
- Guest rating: 8.4/10 (Very good, 2977 reviews)
- Price: $67 nightly, $73 total, Dec 6 - Dec 7, Total with taxes and fees

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.

[See all properties in Windham](https://www.expedia.com/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29&regionId=10053&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Find out more about Windham

### Things to do in and around Windham

Windham, Maine, offers a perfect blend of outdoor adventures and scenic beauty, making it ideal for romantic getaways. Visitors can enjoy a variety of activities, including skiing at the local ski resort and exploring the picturesque landscapes. The area's charm and recreational options make it a great destination for those seeking both relaxation and adventure.

**Shopping**

The [Maine Mall](https://www.expedia.com/Maine-Mall-South-Portland.d6077232.Vacation-Attraction) is a great spot for shopping, located 9 miles away from Windham, featuring entertainment and family-friendly vibes. If you're up for a drive, you can visit the [LL Bean Flagship Store](https://www.expedia.com/LL-Bean-Flagship-Store-Freeport.d6180409.Vacation-Attraction) 16 miles away or explore [The Willows Flea Market](https://www.expedia.com/The-Willows-Flea-Market-Mechanic-Falls.d553248635974793735.Vacation-Attraction), 23 miles from Windham, for unique finds.

**Recreation**

Experience live music at [Thompson's Point](https://www.expedia.com/Thompsons-Point-Portland.d553248622839373742.Vacation-Attraction), a vibrant venue 9 miles from Windham that offers an electrifying atmosphere. For sports enthusiasts, [Hadlock Field](https://www.expedia.com/Hadlock-Field-Valley-Street.d6077238.Vacation-Attraction), also 9 miles away, hosts thrilling games. Enjoy a round of golf at [Riverside Municipal Golf Course](https://www.expedia.com/Riverside-Municipal-Golf-Course-Portland.d6327744.Vacation-Attraction), just 5 miles from Windham, surrounded by beautiful scenery.

**Adventure**

Experience the thrill at [Seacoast Adventure](https://www.expedia.com/Seacoast-Adventure-Windham.d553248621532667986.Vacation-Attraction) with exciting arcade games and family-friendly activities. Hike the scenic [Rattlesnake Mountain Trail](https://www.expedia.com/Rattlesnake-Mountain-Trail-Raymond.d553248621532667989.Vacation-Attraction) for breathtaking views, located 10 miles from Windham. For more fun, visit [Bayside Bowl](https://www.expedia.com/Bayside-Bowl-West-Bayside.d553248621532668077.Vacation-Attraction) to enjoy arcade games and a lively atmosphere, also 10 miles away.

**Nightlife**

Windham offers a cozy nightlife with local favorites like The Frog & Turtle, where you can enjoy craft beers and live music. For a relaxed evening, visit the Windham Public Library's events, or unwind at a nearby bar with friends, soaking in the welcoming community vibe.

### Find the best attractions near Windham

Windham, Maine, is an ideal destination for outdoor enthusiasts and those seeking a romantic getaway. Visitors can explore a variety of attractions, including historic colleges and universities, charming historic houses, and entertainment arenas. The area's points of interest cater to travelers looking for cultural experiences, outdoor activities, and beautiful beach settings, making it a delightful spot for a memorable vacation.

- **[University of New England: ](https://www.expedia.com/University-Of-New-England-Portland.d6176269.Vacation-Attraction)** A modern institution located 7 miles from Windham, the University of New England offers a vibrant campus atmosphere. Visitors can enjoy the blend of academic excellence and city vibes, making it a great spot for a leisurely stroll or to appreciate the architecture.
- **[Portland Museum of Art: ](https://www.expedia.com/Portland-Museum-Of-Art-Downtown-Portland.d6077214.Vacation-Attraction)** Situated 10 miles away, this museum showcases a rich collection of American and European art. With its cultural vibes, visitors can immerse themselves in art exhibitions and enjoy the beautiful architecture of the museum itself.
- **[Cross Insurance Arena: ](https://www.expedia.com/Cross-Insurance-Arena-Downtown-Portland.d6077236.Vacation-Attraction)** Also located 10 miles from Windham, this entertainment venue is perfect for family-friendly events. Experience the excitement of live sports, concerts, and shows, all in a lively atmosphere that appeals to all ages.

### Best time to go to Windham

The best time to visit Windham is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

### Tips to save on your trip to Windham

- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Windham.
- Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget.
- Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties.

## Frequently Asked Questions

### What's the best vacation package for Windham?

For a romantic Windham vacation package, consider a stay at **Dormir,** rated 8.5 out of 10\. This property, located about 7 miles from central Windham and about 3 miles from [Little Sebago Lake](https://www.expedia.com/Little-Sebago-Lake.d553248635976197181.Vacation-Attraction), offers an indoor pool and free breakfast, with travelers often praising the great breakfast and spacious rooms. Its quiet atmosphere and amenities make it a strong choice for couples seeking a relaxing escape in Windham's natural surroundings.

### How can I save money on a Windham vacation package?

When you bundle, you can save up to 30%\*. To save money on a Windham package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. \*Members only. Savings vary.

### What are the top things to do in Windham?

A Windham vacation offers plenty of outdoor activities and scenic views, making it an ideal outdoor and nature destination:

Browse and book [things to do in Windham](https://www.expedia.com/Things-To-Do-In-Windham.d10053.Travel-Guide-Activities) on Expedia.

### Do you need to rent a car in Windham, or is public transport enough?

For a Windham vacation package, driving is generally the best way to explore this outdoor and nature destination. Many attractions, such as Sebago Lake and Highland Lake, are spread out, and traffic can become backed up during popular travel periods. You can call for local taxis. Renting a car offers the most flexibility to visit various lakes, beaches, and other sights at your own pace, especially when booking Windham vacation packages with flights.

### Can I change or cancel my Windham vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

### Do One Key members get extra savings when booking Windham vacation packages?

Yes, members who join our free [One Key™](https://www.expedia.com/welcome-one-key) travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

### Does Expedia offer Book Now, Pay Later Windham vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by [Affirm](https://www.expedia.com/ega/lodging/625310), you can spread the cost of your Windham vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

### How do I find last-minute vacation packages to Windham?

To find last-minute vacation packages to Windham, explore the [last-minute deals](https://www.expedia.com/lp/b/vacations/last-minute-deals) section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

### How does free cancellation work on Windham vacation packages?

Free cancellation on a Windham vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia [help center](https://www.expedia.com/helpcenter) for further details.

### Is it cheaper to book a Windham vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Windham getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

### Why should I book my Windham vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

## Explore a world of travel with Expedia

- [Lodging](?equalTargetTab=tab-0)
- [Flights](?equalTargetTab=tab-1)
- [Packages](?equalTargetTab=tab-2)
- [Cars](?equalTargetTab=tab-3)
- [Vacation Rentals](?equalTargetTab=tab-4)
- [Things to Do](?equalTargetTab=tab-5)
- [Hotels with Free Airport Shuttle in Portland](https://www.expedia.com/Portland-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d181420-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
- [Falmouth Hotels](https://www.expedia.com/Falmouth-Hotels.d6336429.Travel-Guide-Hotels)
- [South Portland Hotels](https://www.expedia.com/South-Portland-Hotels.d6769.Travel-Guide-Hotels)
- [Brunswick Hotels](https://www.expedia.com/Brunswick-Hotels.d7114.Travel-Guide-Hotels)
- [Scarborough Hotels](https://www.expedia.com/Scarborough-Hotels.d6809.Travel-Guide-Hotels)
- [Pet-Friendly Hotels in Portland](https://www.expedia.com/Portland-Hotels-Pet-Friendly-Hotel.0-0-d181420-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Hotels near Portland Intl. Jetport](https://www.expedia.com/Portland-Intl-Jetport-Airport-Hotels.0-aPWM-0.Travel-Guide-Filter-Hotels)
- [Downtown Portland Hotels](https://www.expedia.com/Downtown-Portland-Portland-Hotels.0-n6174134-0.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Portland](https://www.expedia.com/Portland-Hotels-Cheap-Hotels.0-0-d181420-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Portland Hotels](https://www.expedia.com/Portland-Hotels.d181420.Travel-Guide-Hotels)
- [Old Port Hotels](https://www.expedia.com/Old-Port-Portland-Hotels.0-n6172121-0.Travel-Guide-Filter-Hotels)
- [Wells Hotels](https://www.expedia.com/Wells-Hotels.d56045.Travel-Guide-Hotels)
- [Ogunquit Hotels](https://www.expedia.com/Ogunquit-Hotels.d55878.Travel-Guide-Hotels)
- [Oceanfront Hotels in Old Orchard Beach](https://www.expedia.com/Old-Orchard-Beach-Hotels-Oceanfront-Hotels.0-0-d9256-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Freeport Hotels](https://www.expedia.com/Freeport-Hotels.d180773.Travel-Guide-Hotels)
- [Kennebunkport Hotels](https://www.expedia.com/Kennebunkport-Hotels.d10869.Travel-Guide-Hotels)
- [Windham Hotels](https://www.expedia.com/Windham-Hotels.d10053.Travel-Guide-Hotels)
- [Old Orchard Beach Hotels](https://www.expedia.com/Old-Orchard-Beach-Hotels.d9256.Travel-Guide-Hotels)
- [Oceanfront Hotels in Portland](https://www.expedia.com/Portland-Hotels-Oceanfront-Hotels.0-0-d181420-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Flights from Orlando (MCO) to Portland (PWM)](https://www.expedia.com/lp/flights/mco/pwm/orlando-to-portland)
- [Flights from Denver (DEN) to Portland (PWM)](https://www.expedia.com/lp/flights/den/pwm/denver-to-portland)
- [Flights from St. Louis (STL) to Portland (PWM)](https://www.expedia.com/lp/flights/stl/pwm/st-louis-to-portland)
- [Flights from New York (LGA) to Portland (PWM)](https://www.expedia.com/lp/flights/lga/pwm/new-york-to-portland)
- [Flights from Philadelphia (PHL) to Portland (PWM)](https://www.expedia.com/lp/flights/phl/pwm/philadelphia-to-portland)
- [Flights from Cincinnati (CVG) to Portland (PWM)](https://www.expedia.com/lp/flights/cvg/pwm/cincinnati-to-portland)
- [Flights from Dallas (DFW) to Portland (PWM)](https://www.expedia.com/lp/flights/dfw/pwm/dallas-to-portland)
- [Flights from Phoenix (PHX) to Portland (PWM)](https://www.expedia.com/lp/flights/phx/pwm/phoenix-to-portland)
- [Flights from New York (JFK) to Portland (PWM)](https://www.expedia.com/lp/flights/jfk/pwm/new-york-to-portland)
- [Flights from Houston (IAH) to Portland (PWM)](https://www.expedia.com/lp/flights/iah/pwm/houston-to-portland)
- [Flights from Portland (PDX) to Portland (PWM)](https://www.expedia.com/lp/flights/pdx/pwm/portland-to-portland)
- [Flights from Hartford (BDL) to Portland (PWM)](https://www.expedia.com/lp/flights/bdl/pwm/hartford-to-portland)
- [Flights from Baltimore (BWI) to Portland (PWM)](https://www.expedia.com/lp/flights/bwi/pwm/baltimore-to-portland)
- [Flights from Chicago (ORD) to Portland (PWM)](https://www.expedia.com/lp/flights/ord/pwm/chicago-to-portland)
- [Flights from Pittsburgh (PIT) to Portland (PWM)](https://www.expedia.com/lp/flights/pit/pwm/pittsburgh-to-portland)
- [Flights from Detroit (DTW) to Portland (PWM)](https://www.expedia.com/lp/flights/dtw/pwm/detroit-to-portland)
- [Flights from Nashville (BNA) to Portland (PWM)](https://www.expedia.com/lp/flights/bna/pwm/nashville-to-portland)
- [Flights from Boston (BOS) to Portland (PWM)](https://www.expedia.com/lp/flights/bos/pwm/boston-to-portland)
- [Flights from Charlotte (CLT) to Portland (PWM)](https://www.expedia.com/lp/flights/clt/pwm/charlotte-to-portland)
- [Flights from Seattle (SEA) to Portland (PWM)](https://www.expedia.com/lp/flights/sea/pwm/seattle-to-portland)
- [Flights from Richmond (RIC) to Portland (PWM)](https://www.expedia.com/lp/flights/ric/pwm/richmond-to-portland)
- [Flights from Atlanta (ATL) to Portland (PWM)](https://www.expedia.com/lp/flights/atl/pwm/atlanta-to-portland)
- [Flights from Newark Liberty Intl. Airport (EWR) to Portland (PWM)](https://www.expedia.com/lp/flights/ewr/pwm/newark-liberty-intl-airport-to-portland)
- [Flights from Los Angeles (LAX) to Portland (PWM)](https://www.expedia.com/lp/flights/lax/pwm/los-angeles-to-portland)
- [Flights from Jacksonville (JAX) to Portland (PWM)](https://www.expedia.com/lp/flights/jax/pwm/jacksonville-to-portland)
- [Flights from Raleigh (RDU) to Portland (PWM)](https://www.expedia.com/lp/flights/rdu/pwm/raleigh-to-portland)
- [Flights from Washington (DCA) to Portland (PWM)](https://www.expedia.com/lp/flights/dca/pwm/washington-to-portland)
- [Flights from Austin (AUS) to Portland (PWM)](https://www.expedia.com/lp/flights/aus/pwm/austin-to-portland)
- [Flights from New York (NYC) to Portland (PWM)](https://www.expedia.com/lp/flights/nyc/pwm/new-york-to-portland)
- [Flights from Tampa (TPA) to Portland (PWM)](https://www.expedia.com/lp/flights/tpa/pwm/tampa-to-portland)
- [Flights from Indianapolis (IND) to Portland (PWM)](https://www.expedia.com/lp/flights/ind/pwm/indianapolis-to-portland)
- [Flights from Cleveland (CLE) to Portland (PWM)](https://www.expedia.com/lp/flights/cle/pwm/cleveland-to-portland)
- [Flights from Fort Lauderdale (FLL) to Portland (PWM)](https://www.expedia.com/lp/flights/fll/pwm/fort-lauderdale-to-portland)
- [Flights to Portland](https://www.expedia.com/Cheap-Flights-To-Portland.d181420.Travel-Guide-Flights)
- [Flights from Salt Lake City (SLC) to Portland (PWM)](https://www.expedia.com/lp/flights/slc/pwm/salt-lake-city-to-portland)
- [Flights from Columbus (CMH) to Portland (PWM)](https://www.expedia.com/lp/flights/cmh/pwm/columbus-to-portland)
- [Flights from Tucson (TUS) to Portland (PWM)](https://www.expedia.com/lp/flights/tus/pwm/tucson-to-portland)
- [Flights from Miami (MIA) to Portland (PWM)](https://www.expedia.com/lp/flights/mia/pwm/miami-to-portland)
- [Flights from Washington (IAD) to Portland (PWM)](https://www.expedia.com/lp/flights/iad/pwm/washington-to-portland)
- [Flights from Minneapolis (MSP) to Portland (PWM)](https://www.expedia.com/lp/flights/msp/pwm/minneapolis-to-portland)
- [Flights from Portland Intl. Jetport](https://www.expedia.com/lp/airports/pwm/flights-from-portland-intl-jetport-airport)
- [Flights from San Francisco (SFO) to Portland (PWM)](https://www.expedia.com/lp/flights/sfo/pwm/san-francisco-to-portland)
- [Downtown Portland Vacations](https://www.expedia.com/Downtown-Portland.d6174134.Destination-Travel-Guides)
- [Visit Windham](https://www.expedia.com/Windham.dx10053)
- [Quarry Run Dog Park](https://www.expedia.com/Quarry-Run-Dog-Park-North-Deering.d553248621532668094.Vacation-Attraction)
- [Children's Museum and Theatre of Maine](https://www.expedia.com/Childrens-Museum-And-Theatre-Of-Maine-Portland.d6326315.Vacation-Attraction)
- [Eastern Promenade](https://www.expedia.com/Eastern-Promenade-East-End.d6326369.Vacation-Attraction)
- [Two Lights State Park](https://www.expedia.com/Two-Lights-State-Park-Cape-Elizabeth.d6077252.Vacation-Attraction)
- [Thompson's Point](https://www.expedia.com/Thompsons-Point-Portland.d553248622839373742.Vacation-Attraction)
- [Fitzpatrick Stadium](https://www.expedia.com/Fitzpatrick-Stadium-Parkside.d6327715.Vacation-Attraction)
- [State Theatre](https://www.expedia.com/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction)
- [Visit Portland](https://www.expedia.com/Portland.dx181420)
- [Happy Wheels Skate Center](https://www.expedia.com/Happy-Wheels-Skate-Center-Westbrook.d775855402012282880.Vacation-Attraction)
- [Visit Old Port](https://www.expedia.com/Portland-Old-Port.dx6172121)
- [Maine College of Art](https://www.expedia.com/Maine-College-Of-Art-Downtown-Portland.d6077220.Vacation-Attraction)
- [Shaw Park](https://www.expedia.com/Shaw-Park-Gorham.d553248633861906803.Vacation-Attraction)
- [Wadsworth-Longfellow House](https://www.expedia.com/Wadsworth-Longfellow-House-Downtown-Portland.d6077224.Vacation-Attraction)
- [East End Beach](https://www.expedia.com/East-End-Beach-East-End.d6326357.Vacation-Attraction)
- [Bug Light](https://www.expedia.com/Bug-Light-South-Portland.d6077242.Vacation-Attraction)
- [Gray Vacations](https://www.expedia.com/Gray.d6341840.Destination-Travel-Guides)
- [International Cryptozoology Museum](https://www.expedia.com/International-Cryptozoology-Museum-Downtown-Portland.d6326779.Vacation-Attraction)
- [Maine Mall](https://www.expedia.com/Maine-Mall-South-Portland.d6077232.Vacation-Attraction)
- [Mclellan-Sweat Mansion](https://www.expedia.com/McLellan-Sweat-Mansion-Downtown-Portland.d6327527.Vacation-Attraction)
- [Portland Museum of Art](https://www.expedia.com/Portland-Museum-Of-Art-Downtown-Portland.d6077214.Vacation-Attraction)
- [Southworth Planetarium](https://www.expedia.com/Southworth-Planetarium-Oakdale.d6327866.Vacation-Attraction)
- [Falmouth Vacations](https://www.expedia.com/Falmouth.d6336429.Destination-Travel-Guides)
- [Victoria Mansion](https://www.expedia.com/Victoria-Mansion-West-End.d6077228.Vacation-Attraction)
- [Visit Bailey Island](https://www.expedia.com/Bailey-Island.dx6046825)
- [Casco Bay Lines Ferry Terminal](https://www.expedia.com/Casco-Bay-Lines-Ferry-Terminal-Downtown-Portland.d553248621533120972.Vacation-Attraction)
- [Charles Q. Clapp House](https://www.expedia.com/Charles-Q-Clapp-House-Downtown-Portland.d6326305.Vacation-Attraction)
- [Ll Bean Flagship Store](https://www.expedia.com/LL-Bean-Flagship-Store-Freeport.d6180409.Vacation-Attraction)
- [Portland Head Light](https://www.expedia.com/Portland-Head-Light-Cape-Elizabeth.d6077212.Vacation-Attraction)
- [State Street Church](https://www.expedia.com/State-Street-Church-Downtown-Portland.d553248635188831461.Vacation-Attraction)
- [Higgins Beach](https://www.expedia.com/Higgins-Beach-Maine.d6326755.Vacation-Attraction)
- [Fort Williams Park](https://www.expedia.com/Fort-Williams-Park-Cape-Elizabeth.d553248621532668086.Vacation-Attraction)
- [Seacoast Adventure](https://www.expedia.com/Seacoast-Adventure-Windham.d553248621532667986.Vacation-Attraction)
- [Rental cars Portland Intl. Jetport airport](https://www.expedia.com/Car-Rentals-In-Portland-Intl-Jetport.d5068624.Car-Rental-Guide)
- [Car rental Portland](https://www.expedia.com/Car-Rentals-In-Portland.d181420.Car-Rental-Guide)
- [Car rental Windham](https://www.expedia.com/Car-Rentals-In-Windham.d10053.Car-Rental-Guide)
- [Portland Vacation Rentals](https://www.expedia.com/Portland-Vacation-Rentals.d181420.Travel-Guide-VacationRentals)
- [Things to do in Windham](https://www.expedia.com/Things-To-Do-In-Windham.d10053.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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