Fitness-friendly holiday rentals in Cumberland

Designers Dream Home with Pool!

Discover this brand-new, beautifully appointed 2-bedroom home nestled within a secure, private community surrounded by 200 acres of preserved natural beauty. Enjoy full access to outdoor heated pools, a clubhouse featuring a game room (with ping pong, foosball, shuffleboard, and a poker room), and a fully equipped fitness center to keep you on routine. Mingle with fellow guests at the clubhouse or relax in your peaceful, private backyard, and enjoy the perfect balance of activity and serenity.

Lakefront | Dock + Fire Pit Near Sebago & Portland

Experience the charm of Forest Lake just 28 mins from Sebago & Portland! Swim, kayak, paddleboard, or unwind on your private beach. Enjoy BBQs & bonfires in the spacious yard under the stars. Sleeps 7. Fully stocked home with 72" OLED TV, PS5, surround sound, and fast Wi-Fi. New heat pumps ensure comfort year-round. Whether you're after lakeside peace or easy access to southern Maine's best spots, your perfect escape awaits. Explore local trails, beaches, breweries, & classic Maine lake towns.

Home on Historical Island and Saco River (+ Gym)

This four bedroom 1.5 bath home on historic Springs Island in Saco has both the charm and amenities that you need for your next vacation. Stay in this restored new englander on the Saco River in Biddeford where you can enjoy the water at home or you are just a short drive to the many of the most traversed beaches in Maine. You are also within walking distance to thriving downtown Biddeford, its mill district, and all of its restaurants and shops. Guests get access to a private gym as well.

*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.

This special, completely renovated place can host your family gathering or group of friends in an inviting setting. This unique house with a private bar, spa, and a pool table will satisfy all your vacation needs! Located close to everything, but absolutely quite and private 20 acres property! It is situated on a ridge with a spectacular mountain view. Our house offers comfort & entertainment. The property will give you the full vacation in the woods experience. This is just what you need!

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

Romantic New England Historic Schoolhouse c1866

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond and tennis court.

The Hill's on Buttonwood

We are out of the baby stage and ready to share our home while away. Our home is a great house for entertaining or just relaxing without feeling cramped. There are places for everyone, from the heated pool, the patio, or outdoor activities, to the many living/sitting rooms, gym or theater/game room. Located just minutes from the airport and minutes from downtown in the historic Stroudwater district or Portland. Sitting on nearly an acre on a small cul-de-sac of similar stately homes.

Maine Lakes Region house (private hot tub)

Cozy new construction, Chalet style, year-round house, on 9 wooded acres. Lots of Privacy, Short drive to Ski slopes, snowmobile trails, hiking, or beautiful lake to swim, or kayak. Gage beach a 10-minute drive. Close to great hiking, Also Shawni peak and Sunday River. Great restaurants, Mt Washington, NH shopping outlets. Full Desk / office, 200 mb of streaming. Wi-Fi, Netflix via ROKU, Canines only, NO CATS, NO EXCEPTIONS. Portable generator in the event of a power failure provided.

The Ogunquit House Downtown | Walk 2 beach HotTub

ULTIMATE OGUNQUIT BEACH HOUSE! Renovated & fully equipped private oasis located in the heart of beautiful downtown Ogunquit, ME Park on site & walk to the beach, restaurants/bars & village shops all in under 5 minutes! Ideal for families, friends or couples looking for a perfect beach getaway. Our goal is to provide you with everything you need so there’s less time spent on essentials & renting equipment. Queen, double bunk bed, & 2 pull out couches can sleep 6 comfortably!

White Mountain Mansion -Secluded property, pets OK

Tucked away on five acres of beautiful wooded mountain land, we have our beautiful 5 bedroom, 5 bathroom home. 10 min outside of North Conway! Not only do we have all common amenities, we have some pretty special ones too: a movie theatre room, a gym, surround sound in 3 rooms, an upstairs lounge area equipped with a Billiards, Ping Pong, and a poker table! Not to mention a beautiful wood burning fireplace, and extra sleeping options for guests (that aren’t factored into bedrooms)

Sunny 2-BR 5 min to Bates & River Trails

A classic 1920s Maine bungalow lovingly renovated. Our pet-friendly plant-filled home is an Auburn favorite. Unwind in our sunlit yoga studio - ideal for meditation, painting, or movement. Whisper-quiet heat-pump HVAC plus a hybrid water heater for eco-friendly comfort. Enjoy the rewilded pollinator garden of native Maine blooms. 5 min to Bates & St. Mary’s, 40 min to Portland, Brunswick, Bath, and Freeport. Stays of 14+ nights include complimentary weekly cleaning.

Exclusive Glass Wall Waterfront Hot Tub, Fireplace

Rushing Water will flow right by your bed overlooking the most pristine, undeveloped river in Maine. Oasis with no one in sight. Complete privacy in the hot tub overlooking private waterfront. Wall of windows with mirror tint. Hot tub & outdoor shower just outside the front door. Hammocks, to relax in or hiking trails to discover right out the front door. Enjoy eating or lounging on the riverbank overlooking the Rushing Water. Professionally Designed Countryside cabin.