Waterfront vacation rentals in Cumberland County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Cumberland County

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Top guest favorite

Guest suite in Portland

4.99 out of 5 average rating, 325 reviews

Sunny West End Guest Suite w/Harbor Views and Pool

Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. This garden oasis with stone walls and salt water pool (open seasonally) is walking distance to downtown. (Portland City Permit: 20185360-ST) Your safety is important to us! We are following strict guidelines for sanitizing all linens, towels, furniture, objects and surfaces. Airbnb has an incredibly thorough and helpful protocol! All doorknobs, light switches and hand-touched surfaces will also be alcohol sanitized for your arrival! Here is a link to the protocol we are following: https://www.airbnb.com/resources/hosting-homes/a/airbnbs-5-step-cleaning-process-explained-187. Please let us know if you have any questions! This guest suite is a private, two-floor space attached to our house. It has its own front and back entrances and is separated by locked doors upstairs and downstairs from the main part of the house. The suite is light and sunny and a wonderful place to rest. The downstairs sitting room has a table for two and built in seating for relaxing and enjoying the water views or watching tv. The bedroom and bathroom are upstairs with lovely views. You will given your unique code for the guest suite door which enables you to come and go on your own timing. Parking is always available in front of the house or within a block. Please note that parking is prohibited on our side of the street on Monday nights through Tuesday mornings the 2nd and 4th Monday of the month. You can park on the opposite side of the street. The guest suite is attached to our house, but with its own front and back entrances. The day before you arrive we will send you instructions about your arrival. There is a key code so you can enter on your own. We may see each other on the back deck or in the yard at the pool. We have two dogs and you might see them in the yard and also coming up the stairs to our back deck door. We are right next door if you need anything or have any questions, and are also very conscious of your privacy. Please feel free to reach out if you need anything. We love Portland! Just let us know if you would like advice on local hikes, beaches, entertainment or great food. Portland has incredible restaurants! Most within walking distance from the house. The house is in the historic West End neighborhood overlooking the working harbor of the Fore River. Within walking distance are Portland's Old Port and Arts Districts, as well as the Saturday Farmers' Market in Deering Oaks Park. Parking is very easy on the street in front of the house. You can drive to local spots like the beautiful lighthouse at Fort Williams in Cape Elizabeth or the beaches in Scarborough, but you can walk to downtown Portland in 15-20 minutes. It's great to visit Portland on foot. You can walk Danforth Street all the way down to the Old Port shopping area. Here are directions for a nice walk to the Old Port: Turn right on Danforth when leaving the house. Take your first left on Emery Street. At the four way stop, turn right on Spring Street. Take Spring Street for just over a mile. After passing Temple Street, take your first right onto Exchange Street. This is the heart of the Old Port. Have fun!! Please Note: All Guests agree to indemnify and hold the Property Owners harmless from any liability for personal injury or property damage sustained by Guest or parties invited onto the property by Guest.

Guest favorite

Home in Naples

4.99 out of 5 average rating, 124 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Guest favorite

Home in Falmouth

4.88 out of 5 average rating, 253 reviews

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!

Superhost

Treehouse in Sanford

4.9 out of 5 average rating, 515 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Guest favorite

Cottage in Topsham

4.93 out of 5 average rating, 252 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Top guest favorite

Home in Windham

4.94 out of 5 average rating, 136 reviews

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.

Top guest favorite

Guest suite in Freeport

4.97 out of 5 average rating, 232 reviews

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.

Top guest favorite

Apartment in Gray

4.95 out of 5 average rating, 142 reviews

Two bedroom duplex across st from crystal lake

Relax, have fun, spend quality time with friends and family right here at our quiet little place. Two bedrooms, three beds, one pull out couch, we can accommodate up to six guests. We have walking trails, firepit, and a barbecue area. The house sits across the street from crystal lake, with a boat launch 3/4 mile down the road with a parking area. An easy 20-minute drive to Portland. Supermarket, gas station, and restaurant less than five minutes away and ten minutes from Gray exit to 95.

Superhost

Cabin in Raymond

4.93 out of 5 average rating, 154 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Guest favorite

Tiny home in Bowdoinham

4.91 out of 5 average rating, 114 reviews

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

Guest favorite

Cabin in Freeport

4.97 out of 5 average rating, 509 reviews

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

Top guest favorite

Barn in Portland

5 out of 5 average rating, 430 reviews

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The newly created studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite glass of wine under the splendid backyard grape arbor.