Windham Vacation Rentals

Compare 6 vacation rentals.
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Make Windham your next getaway

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.

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House rentals

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Windham vacation rentals for every getaway

Dog-friendly Hot tub Internet
Overlook at Highland Lake
3 Bedroom | 2 Bath | Sleeps 6

Overlook at Highland Lake - Windham, ME

$325 avg / night
Sheldrake Cove Retreat
3 Bedroom | 2 Bath | Sleeps 6

Sheldrake Cove Retreat - Windham, ME

$187 avg / night
Highland Playhouse
3 Bedroom | 2 Bath | Sleeps 7

Highland Playhouse - Windham, ME

$300 avg / night
Highland Lake House
4 Bedroom | 2.5 Bath | Sleeps 8

Highland Lake House - Windham, ME

$258 avg / night
Cozy Sebago Basin Cabin
1 Bedroom | 1 Bath | Sleeps 6

Cozy Sebago Basin Cabin - Windham, ME

$238 avg / night

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Recent Windham vacation rental reviews

Location was about 30 Min drive from Portland, Freeport etc. Having life jackets in multiple sizes and kayaks to take out on the lake was such a great experience. We honestly didn’t want to leave the house.
Lu Q. | Sep 2023
Great place! Wonderful location and gray smenities
Sue W. | Sep 2023
We had a wonderful week at this rental. It has a great layout, plenty of space for 6 of us. The location is so lovely - we enjoyed the loons the on the lake, seeing the moon rise, and the peaceful water views. The porch and the sitting room off the upstairs bedroom were both favorite spots during our stay. The only issue we had was that the yard between the house and dock was unusable - super muddy/wet. I recognize this has been an exceptionally rainy summer, but the rain started in June and this was the end of August, so it is something that should have been dealt with by now. It was challenging to get to the dock, and the fire pit was surrounded by mud. The previous guests' dogs also left some presents around the yard that we had to clean up when we arrived. For future renters, we had wondered about some of the details beforehand that weren't in the listing. Hope this helps: -There is both a Keurig machine (we did not use this) and a regular coffee maker (we used this, there were filters provided, it worked great) -There were 2 stand up paddle boards with 1 stand up paddle board paddle (we did not use these - the lake was a bit windy) -There was 1 double person kayak and 2 single person kayaks with enough kayak paddles for all (we used the double kayak and a single kayak - both were great) -There was a row boat but no oars (we did not use) -There was a bin of life jackets -The grill had gas but did not work -The patio table had gas and you could turn on a fire in the middle of it (we did use this and roasted marshmallows there since we couldn't sit around the fire pit) -There was only one beach towel that we could find, although there were extra bath towels -Kitchen had everything we needed for cooking, very well equipped -There were a lot of fans around and one air conditioning unit in an upstairs window (we didn't need these in late August - it was cool enough) -The lake area is extremely shallow around the dock - absolutely no jumping in. In fact, you could walk way out in the water and it was still quite shallow -Lots of games, puzzles, books, magazines, etc. provided -Clearly a very dog-friendly rental (dog bed, bowls, toys, etc.) Overall, we had a really nice time in this cute home with a great lake view.
Kelly W. | Sep 2023
Windham vacation rental FAQ

Yes, 17 of our Windham homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 49 of our Windham vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Windham vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Windham team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Windham, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

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