Holiday Rentals in Windham
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Holiday Rentals in Windham

Classic Maine Cabin, Private Waterfront Easy Access to Nearby Amenities

The Weldon Hotel

68 East Grand Ave

Charming 2-bedroom house with AC, WiFi in fantastic Old Orchard Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Gorgeous ocean-front home with stunning beach views

100 feet from the ocean 3 bedroom cottage 420 friendly

AmongstTheAspens - Tiny House in a serene location

2 bedroom cottage

Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Little Miss Cottages

Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Lakefront Cottage: Boat Dock, Patio & Kayaks!

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Other types of properties in Windham you may be interested in

Clarion Hotel Portland
Holiday Accommodation Windham
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Windham are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Windham itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Windham holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Windham, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Windham with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.