House holiday rentals in Cumberland

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Cozy Cottage Retreat near Breweries & Airport

Cozy Cottage Retreat w/ Loft near Portland Welcome to your Maine escape. Reno barn offers a warm, cottage-inspired atmosphere with character, an open loft, and inviting spaces for rest and connection. Located mins from the airport and within walking distance to Allagash Brewing Company and other local favorites. A quick drive to downtown Portland, beaches, lighthouses, and live music. End your evenings on the private back deck — wine in hand, stars overhead, and nothing but quiet around you.

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.

The Outlet Studio, Rustic Comfort w Fireplace

Conveniently and perfectly located! Our studio is in a private building on a quiet dead end street yet walking distance to L.L. Bean, Bow Street Market, Leon Gorman Park, restaurants, breweries, live music, outlet shops, Freeport Farmers Market, the Amtrak station and all that downtown Freeport has to offer. A short drive to Wolfe's Neck State Park, Bradbury Mountain State Park, Mast Landing Audubon Sanctuary, the Desert of Maine, Winslow Park, farm stands and the beautiful mid-coast coast.

Higgins Beach *New* Beach Home & Private Offices

Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

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.

Spacious Cozy Home in Freeport, ME

Come enjoy Freeport, Maine in this beautiful home. One mile from the downtown shopping district and the L.L. Bean flagship store. This two family home is being rented as a single family home, giving you the benefit of two kitchens and two living rooms. Perfect for families and groups of friends. The two sides are connected via a door similar to adjoining hotel rooms. For winter guests our pond is great for skating and we have a variety of skates available upon request.

The Barnhouse with hot tub

Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

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.

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.

Beautiful +Nostalgic + Coastal Maine Cottage

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

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.