Holiday houses in Cumberland

Buoys on Bates | Couples' Cottage near Portland

Buoys on Bates is a newly renovated, contemporary cottage 15 minutes from Portland and moments from Yarmouth's historic Main Street. Step into a spotless, light filled space with a full kitchen, fast 350 Mbps wifi, premium Tuft & Needle queen bed, in-unit washer/dryer, efficient A/C, and Level 2 EV charger right at the door. Walk to shops, restaurants, and the Royal River, then set out for Portland, Freeport, beaches, and breweries. Buoys on Bates is your easy, comfortable base for all of Maine.

Location · Family · Layout

Tranquil Home on Nature Preserve

Beautiful modern home with large windows & ample natural light. Located in a tranquil neighborhood on a nature preserve. Each of the 3 bedrooms is equipped with a smart TV, heat pumps/ac units, high speed Wi-Fi, & all the amenities to ensure your comfort. Enjoy high end appliances, propane fireplace, luxury hot tub, back patio & fire pit. Conveniently located in Cumberland with easy access to I95, Portland, Sebago Lake, &Coastal Maine. Trail access to Knight’s Pond Preserve along property.

Location · Family · Checkout

Water views, privacy, decks, minutes to Portland

Wake up to coffee and breakfast on the deck watching eagles and other native birds of Maine then walk the private botanical garden. This is an deal location for a Maine getaway. This modern chalet sits on 4 private acres 15 minutes to Portland on the Cumberland Foreside. Enjoy panoramic water views, expansive decks with tons of outdoors seating, 2 minutes from the marina, town landing beach, 5 minutes to Sandy Beach, walk to mountain biking & hiking trails. Open concept perfect for relaxation.

Location · Family · Hiking

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.

Value · Family · Hiking

Falmouth Waterfront Carriage House Apt

Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

Family · Location · Parks

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Value · Family · Indoor spaces

Rustic charm close to Portland

Peaceful and private. My home is a country getaway with unique charm and has a feeling like no other. Just voted the safest town to live in Maine, located close to downtown Portland, the Portland Jet Port, Freeport, beautiful Maine beaches, apple orchards, a Gorgeous wedding venue a mile away called Caswell Farm and close to trails for hiking, my home has many options. It's a great spot for a group of 6 or a couple of 2 to unwind.

Location · Family · Nearby

Close to Breweries, Outlets, and Portland Food!

Newly renovated and centrally located in charming Yarmouth Village! Enjoy a short walk to shops and restaurants, drive 15 minutes to Portland Old Port and renowned restaurants, or 5 minutes to Freeport Breweries/Outlets. Maine Beer Company, Mast Landing, LL Bean, Ottos, Royal River Grill all just minutes away. This is the perfect pit stop on your way to Acadia/ski mountains or to plan a day trip up the coast to Boothbay Harbor.

Family · Location · Access

Beautiful +Nostalgic + Coastal Maine Cottage

Conveniently located 15 minutes from Portland Jetport and 10 minutes from Old Port in downtown Portland, this renovated 1850's, charming, and sunny historic home is perfect for your Maine getaway. It is a fantastic home-base for exploring Southern and Midcoast Maine while enjoying close proximity to Portland's award-winning restaurants and attractions as well as beautiful beaches, islands, museums, lighthouses, and much more.

Location · Family · Hospitality

Charming Guest House: Accessible

Charming guest house with a private entrance, modern kitchen, and cozy living space. Accessible features include an elevator and curbless showers for easy mobility. Relax in the garden or explore nearby attractions like Freeport Outlets, L.L. Bean and Portland. Perfect for families, couples, or guests with accessibility needs, offering a peaceful retreat with easy access to shopping, dining, and outdoor activities

Location · Family · Nearby

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

Value · Location · Accuracy

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!

Value · Location · Barbecue