Holiday rentals with outdoor seating in Cumberland

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.

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.

Waterfront Private Apartment just 5 min to LLBean!

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

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.

Modern cozy cottage in historic coastal Maine

Contemporary, newly-renovated cottage between Portland and Freeport. Spotless interior w/ full kitchen, Netflix/AppleTV+, premium Tuft+Needle bed, and W/D. EV charging available. Walk to shops, restaurants, and the scenic Royal River. Easy drives to downhill skiing and iconic beaches, Portland's renowned restaurants, LL Bean flagship, and top-rated Maine Brewing. Half way between Boston and Sugarloaf. Your ideal base for Maine adventures.

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.

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 in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018

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.