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Windham Vacation Rentals

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Lady Pepperell - Windham, ME Vacation Rental

Lady Pepperell

Windham, ME
3 Bed 1 Bath Sleeps 8
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Genes Lodge - Windham, ME Vacation Rental

Genes Lodge

Windham, ME
5 Bed 3 Bath Sleeps 12
- - - 140 140 140 140 140 150 150 140 140 140 140 140 150 150
It's Jest A Camp - Windham, ME Vacation Rental

It's Jest A Camp

Windham, ME
1 Bed 1 Bath Sleeps 6
- - - 85 90 90 90 90 115 115 90 90 90 90 90 115 115
New Marblehead Lodge - Windham, ME Vacation Rental

New Marblehead Lodge

Windham, ME
3 Bed 1 Bath Sleeps 8
- - - 99 115 115 115 115 145 145 115 115 115 99 - - -
The Beach House - Old Orchard Beach, ME Vacation Rental

The Beach House

Old Orchard Beach, ME
4 Bed 1.5 Bath Sleeps 10
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Selah Lakefront Retreat - Standish, ME Vacation Rental

Selah Lakefront Retreat

Standish, ME
4 Bed 3.5 Bath Sleeps 10
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Grand Avenue Escape - Old Orchard Beach, ME Vacation Rental
- - - - 130 135 135 135 180 180 135 135 135 135 135 180 180
Woodland - Portland, ME Vacation Rental

Woodland

Portland, ME
3 Bed 1.5 Bath Sleeps 8
90 - - - - - - - - - 99 115 115 115 99 - -
The Dunegrass Cottage - Old Orchard Beach, ME Vacation Rental
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The Retreat At Upper Range Pond - Poland, ME Vacation Rental
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The Shore Road Escape - Cape Elizabeth, ME Vacation Rental
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Willard Square Getaway - South Portland, ME Vacation Rental
- - - - - - - - - - - 135 140 140 140 180 180
Willard Square Overlook - South Portland, ME Vacation Rental
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Willard Retreat - South Portland, ME Vacation Rental

Willard Retreat

South Portland, ME
2 Bed 1 Bath Sleeps 6
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The Beach House at Kennebunk - Kennebunk, ME Vacation Rental

The Beach House at Kennebunk

Kennebunk, ME
5 Bed 4.5 Bath Sleeps 10
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The Ocean Street Barn House - South Portland, ME Vacation Rental
99 99 - 85 125 - - - - - - - - - - - -

About Windham

Barely 12 miles northwest of Maine's largest city is a quiet residential community that was built upon agriculture. The town of Windham, now home to 17,000 residents and the villages of North and South Windham, still acts as a tether between the past and present. You'll find historic buildings, quiet lakeshores, and tranquil paths and preserves - all just a short drive from the working port of Portland and its thriving culinary scene. So make a reservation at one of our Windham vacation homes and enjoy the very best of both worlds.

Where is Windham, ME?

Nestled between bustling downtown Portland to the east and the shores of Sebago Lake to the west, Windham has become a primarily residential area (with a large commercial center) since its settlement by farmers in the mid-18th century. The town sits just 12 miles northwest of Portland, 20 miles north of the ocean shores of Old Orchard Beach, and 31 miles south of downtown Lewiston.

Things to Do in Windham, ME

Get to know Windham by taking a leisurely drive among historic mills and one-room schoolhouses that have since been converted to other uses. Photographers will delight in a glimpse of the Babbs Covered Bridge, which first spanned the Presumpscot River in 1840 and was beautifully rebuilt after a fire in 1973.

Escape into nature by exploring 25 preserves, miles of public access trails, and 1,400 acres of land protected by the Presumpscot Regional Land Trust. Anglers will find public spots for fly fishing in the Presumpscot River watershed, birders can retreat to the 17-acre Pringle Wildlife Preserve to view ducks and blue herons, and hikers can walk through rolling hills and forest wetlands at the Black Brook Preserve. Come wintertime, these lands are also peaceful options for cross-country skiing and snowshoeing.

Spend summer days at the nearby Tassel Top Beach, a 35-acre park on the shores of Sebago Lake with a buoyed swim area and more than 900 feet of soft sand. Windham is also home to a stretch of the Sebago to the Sea Trail, a walking path that links the communities of Standish, Windham, Gorham, Westbrook, Portland, and Falmouth between Sebago Lake and Casco Bay.

Day Trips from Windham, ME

Thanks to their rural-yet-central position in the greater Portland region, our Windham vacation rentals provide guests with endless options for unforgettable day trips. 

To further explore Maine's deepest and second largest lake, head 20 miles northwest to Sebago Lake State Park, where you can fish, snowshoe, or lounge on the beach at one of Maine's five original state parks. You'll find even more summer fun on the sandy shores of Old Orchard Beach 20 miles south, where you can dip your toes in the cool Atlantic Ocean, snack on french fries at the Old Orchard Pier, or thrill your kids with a few rides at the beachfront Palace Playland.

In the mood for a few more creature comforts? Take a tour of the renowned Allagash Brewing Company just seven miles south of Windham, or head 24 miles east to stock up at the flagship L.L. Bean in Freeport. Just be sure to save time for the many charms of downtown Portland, where you can grab breakfast treats at Standard Baking Co., take ferry rides into Casco Bay, or sit down for locally sourced dinners at the incredible Eventide Oyster Co.

Let our Windham vacation homes give you a taste of Maine's unrivaled beauty - book your getaway today!

Photo Credit: Jack Flanagan via Flickr

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