12 Amazing Maine Vacation Rentals On The Water

Kicking off the list in luxury, we have this amazing oceanfront home in charming York. It may cost a pretty penny, but as one review notes, “you get what you pay for.” Two decks and a large yard with plenty of outdoor seating overlook the water. Plenty of parking is available and the house rental comes with a few bikes as well. Go all out and hire the private chef for cooking classes or to prepare meals. If this property isn’t available during your desired dates, check out this premier host’s other York Beach rentals: this three-bedroom oceanfront home or this three-bedroom seaside bungalow.

Perched on cliffs at the mouth of Perkins Cove, this three-bedroom vacation rental overlooks the Atlantic in beautiful Ogunquit, Maine. Explore the Ogunquit American History Museum next door and Ogunquit Beach down the street. Restaurants and shops are a short walk away in Perkins Cove or a longer walk to town via the Marginal Way trail.

One of the original grand beach mansions in quaint Kennebunkport, this enormous eight-bedroom 19th-century shingle-style home is simply stunning. Call dibs on the oceanfront room on the top floor so you can soak in the claw foot tub and sip morning coffee or evening cocktails on the private balcony. Otherwise, you can always take in exquisite water views from the wraparound porch, which even has a screened-in section.

Pick fresh blueberries right off the front porch in August. Walk to town or the beach.

The hosts of this luxurious beachfront property contend that Old Orchard Beach is the most beautiful beach in Maine. Find out for yourself with spectacular ocean views from the decks. Watch the sun come up over the water as you sip your morning coffee. Walk along the beach for miles during low tide. Other features of this home include a pool table, bar, and elevator. Just 30 minutes from Portland, this is a great jumping-off point to visit the surrounding area.

Looking to stay in Portland proper? It doesn’t get much better than this waterfront penthouse suite! Located in a historic 19th-century brick building, this condo has exposed beams and brick and whitewashed wood walls. Go up to the rooftop deck to watch the yachts come in and out of the harbor and enjoy views of the city. Stop at the famous DiMillo’s On The Water floating restaurant for dinner or a drink.

Park in the spot provided in the lot next door and explore several must-see spots nearby. Sample seafood from Harbor Fish Market and J’s Oyster and try a Maine potato donut from The Holy Donut. Take the ferry to visit the islands of Casco Bay. Shop on Exchange Street and sip on a stellar selection of craft brews at Novare Res Bier Cafe. Grocery stores such as Whole Foods, Trader Joe’s, and Hannaford are all within a mile of this downtown vacation rental.

Watch the ever-changing tide and shorebirds from the screened-in porch or patio at this birder’s paradise in fantastic Freeport, Maine. Relax in the hot tub and rinse off in the outdoor shower.

Paddleboards and canoes are included. Check out Wolfe’s Neck Woods State Park nearby as well as restaurants, shops, and many other activities.

Perfect for a family reunion or retreat, this six-bedroom coastal vacation rental offers incredible ocean views. Even though this home was built before 1900, you won’t be fighting for the bathroom with one bath (with shower!) per bedroom. Situated at the very top of the house, the penthouse suite features a private balcony and jacuzzi tub.

Take in idyllic views from the spacious slate patio while enjoying a family-style meal. Sip your morning coffee or evening cocktail on the dock. If you’re lucky, you can flag down a local lobsterman to purchase some fresh-out-of-the-water lobsters to boil for dinner. You may even spot a seal in the water.

Floats and mooring are available for those who want to bring their own boat. Need more space for a larger group? Other rentals on the estate are available, including The Boathouse Cottage (sleeps two) and Landings East (sleeps four).

Just outside downtown Boothbay Harbor, this lovely three-bedroom cottage sits on the tranquil tidal waters of Mill Cove, where you can watch the comings and goings of waves and wildlife. Park in the driveway and walk to shops, restaurants, and area attractions. Gift shops and artisan wares and coastal-inspired restaurants are all just a short stroll away. Take to the waters on Cap’n Fish’s Whale Watch or cruise the harbor and open ocean aboard the Schooner Eastwind or Schooner Lazy Jack.

The only thing you’ll have to complain about when staying in this historic five-bedroom house is being woken up by the lobstermen in time to witness the stunning sunrise over the harbor. Buy lobster right off the docks in the harbor to boil back at the house. Relax on the deck or take out the double kayak, rowboat, or fishing poles. Croquet sets, kids’ bats and baseballs, and other games are included with this rental. Kids will love the baseball field behind the house.

Bringing a boat? The boat ramp is just down the hill at the public landing and moorings are available.

Explore the village of Tenants Harbor and nearby towns. The area also offers great hiking.

Located on a quiet cove, these two cottages are in one of the most desired areas of Lake Megunticook, just a couple of miles from quaint Camden’s harbor. The “Lower Camp,” a charming century-old cottage, sits on the water’s edge and boasts a screened-in porch, while the “Upper Camp” lies on a wooded slope across the street and has a fireplace. Swim and kayak off the beach!

If you are picturing staying in a cabin on a lake in Maine, this three-bedroom log cabin rental on Phillips Lake is your spot. This pristine lake offers swimming, boating, and fishing. In the fall, take in beautiful foliage views from the deck. Winter offers excellent ice fishing and trails for snowmobiling. Explore nearby Ellsworth (13 miles), Bangor (15 miles), Bar Harbor (33 miles), and Camden (56 miles). For those who want to go hiking, Acadia is also less than an hour away.

Nestled on a wooded lot overlooking Frenchmen’s Bay, this chalet features ocean views from nearly every room. Watch the lobster boats check their traps in the morning from the large deck, which is also a great place to catch the sunset. Walk down the hill to the boardwalk to access the rocky beach. If you need more space for a group or this place isn’t available during your desired dates, check out the host’s nearby Bar Harbor log cabin.

Located at Sunday River Resort, this spacious ski chalet sleeps up to 25, plus pets! Send the kiddos down to the “Kid’s Cave” (complete with PlayStation) and cozy up by the fire or relax in the hot tub on the large deck. There’s also a fire pit outside and a cornhole set.

The rental even features a boot and mitten dryer, which will come in handy since it’s just around the corner from the Road Runner ski trail. In the other direction, a five-minute walk takes you to South Ridge Lodge, the ski lift, the apres-ski bar, ski rentals, and a grocery store. Definitive Brewery can also be reached on foot in less than 10 minutes.