Vacation rentals in Cumberland County

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Sweet 1-Bedroom Apartment in Vintage Village Cape

Built roughly 200 years ago, the traditional cape housing this first-floor apartment is located on a hilltop above the Royal River, just steps from restaurants, trails, and waterfront. It's been thoroughly renovated, and features pretty much all the comforts of home—including a full kitchen with dishwasher, a wood-burning fireplace insert, an all-natural mattress (super comfy), and a clawfoot tub-equipped bathroom. Oh, and if you're bringing a third, let me know—and I'll roll in the rollaway.

Cozy & Convenient Cumberland Guest Cottage

Make yourself at home in this quaint, private guest cottage, perfectly nestled halfway between Portland and Freeport. This detached guest cottage makes a perfect overnight spot as you make your way up the coast, or a home base as you explore Portland, Freeport and the whole breathtaking Casco Bay area. With a kitchenette, bedroom and living area, the cottage is ideal for solo travelers, couples, or a pair of friends looking for a comfortable home base while they explore southern Maine.

LunaSea Suite

Be our guests and enjoy this dreamy, romantic little getaway and all that Saco and surrounding areas have to offer! Direct access to the River Walk. Short 5 minute walk to downtown Saco, Amtrak station, and 10 minute walk to downtown Biddeford. Visit our amazing shops, breweries, restaurants and cafes! Bayview Beach 3 miles OOB Pier 4.4 miles Private entrance and deck with outside fireplace. Hosts, Melissa and Doug, are quiet and considerate early risers with 2 friendly pups

Minutes to Portland | Spacious | One Bedroom

Conveniently located in the charming Cumberland Mills neighborhood of Westbrook, this spacious one bedroom Victorian apartment offers easy access to Portland, the jetport, the highway, Rock Row, and other Westbrook attractions. Delicious eateries, local breweries, and Riverbank Park are within walking distance. This apartment comes fully furnished with a comfortable queen bed in the bedroom, a dedicated workspace, a Pack n' Play, and a pullout sofa bed available upon request.

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C when needed. Please, no smokers, kids under 13, or guest pets. STHR-000718-2018

Great Goat Get-away in Southern Maine!

This quiet and cozy house is located in the woods at the renowned Ten Apple Farm. Centrally located in Southern ME, we're just a short drive from Portland, lakes, ski areas, LL Bean and more! On the farm you can meet and interact with our herd of goats, sheep, pigs and chickens, learn to milk, collect eggs, and arrange on of our famous goat hikes!

Farmhouse stay, near lakes and St. Joe's College

Charming 2 story, 2 bedroom antique farmhouse apartment within walking distance to a quaint pond. Located minutes from St. Joseph's College, Sebago Lakes region, fly-fishing on the Presumpscot River, premier mountain biking and hiking trails. 15 miles to downtown Portland’s famed restaurants, breweries, and shopping.