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Maine has undoubtedly earned its nickname “Vacationland”. In fall, folks flock to the state’s coastal gems, attend seasonal festivals, and hike scenic trails. With the outdoor attributes alone, it’s easy to have a staycation here. But being able to retreat to a stunning rental or hotel makes it even better! While some places in Maine do shut down around mid-fall, these places take advantage of one of Maine’s most beautiful seasons – autumn!

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Chebeague Island Inn - Chebeague Island Chebeague Island Inn
Chebeague Island Inn

Chebeague Island Inn - Chebeague Island

One of the best resorts in the U.S. for viewing fall foliage, Chebeague Island Inn has been awarded numerous honors for its exceptional place within the travel scene. However, the inn plays off of its history and has managed to stay remarkably simplistic while still feeling quite high-end. The interiors have been lovingly preserved and restored, exuding much of the original wood from the early 1900s. Nestled on an island in Casco Bay, there’s a sense of remoteness, while there are boutiques, golfing and beaches.

Lodge at Moosehead Lake - Greenville Lodge at Moosehead
Lodge at Moosehead

Lodge at Moosehead Lake - Greenville

Lodge at Moosehead Lake sits further inland, near the other side of the state. Of course, Maine has many incredible lakes available to travelers who aren’t making their way through the coastal region. The lodge is proximal to incredible waterfront terrain, and each room features views of the surrounding woods. So yes, the changing leaves envelop the property. Start your day with a carefully cultivated breakfast of fresh ingredients. The lodge uses local dry-aged meats, seafood, berries and a wealth of other regionally sourced foods.

Pilgrim's Inn - Deer Isle Pilgrim's Inn
Credit: Pilgrimsinn.com
Pilgrim's Inn

Pilgrim's Inn - Deer Isle

One of Maine’s gorgeous coastal getaways, Pilgrim’s Inn was built in the 1700s, on the lovely Deer Isle. While still feeling luxurious, the Inn feels like home. Enjoy a local beer or steamed clams at the tavern. Or the sea monster chocolate ice cream with a secret ingredient – seaweed! Breakfasts are individually prepared with ingredients from the garden. Nearby you’ll find unparalleled fall hikes among granite, and calm kayaking waters.

Crow’s Nest Tiny House - Durham Crow’s Nest Tiny House
Credit: airbnb.com
Crow’s Nest Tiny House

Crow’s Nest Tiny House - Durham

Durham is only a skip away from Freeport, where travelers can explore LL Bean’s flagship location and the oceanfront. There’s also quaint shops that are perfect for visiting on a crisp fall day, and a place to get killer whoopie pies. But you can also just chill at this clean-cut tiny home, which sits on open farmland, being bordered by trees. Sleep under a skylight that peers toward the sparkling night sky, and in the morning don’t be surprised to see cows and chickens in the field.

Bohemian Bungalow - Bangor Bohemian Bungalow - Bangor
Credit: airbnb.com
Bohemian Bungalow - Bangor

Bohemian Bungalow - Bangor

Whimsical vibes run through the veins of this 1950s bungalow. Staying true to its artistic nature, guests will find a nice balance of colorful and eclectic. Bangor is a town a little bit inland and is the home of the beloved Stephen King. Activities that incorporate some of King’s writing inspiration, is one of the key features of this area. However, the quaintness of downtown shouldn’t be overlooked, and it’s particularly stunning during autumn.

9-Bedroom Estate with Movie Theater - Newry 9 Bdrm Estate Sleep 26
Credit: Airbnb.com
9 Bdrm Estate Sleep 26

9-Bedroom Estate with Movie Theater - Newry

Just about every over the top feature you can think of is at this enormous estate, near Sunday River, a prominent ski area in the winter. The valley has exceptional color changes during the fall, and many trees surround the gigantic home. The massive pool is open until mid-October, and two hot tubs are also onsite. Other things to note are a movie theater, multiple spa bathrooms, and extensive game areas. It’s also dog friendly!

62 Views - Portland 62 Views
Credit: Airbnb.com
62 Views

62 Views - Portland

While Maine has gorgeous remote coastal villages, mountains, and sparkling lakes, fall time in the city is magical in its own right. When in Portland, you’re still close to the water. Seafood can be found around every corner. And many of the quaint shops and cafés offer special seasonal treats from pumpkin donuts to coffee! Then, of course, you have all the perks and adventures to be found amongst the more developed area. This apartment is newly renovated and features the best-elevated deck to view the surroundings.

La Perla Cottage - Ogunquit La Perla Cottage in Ogunquit, Maine
Credit: Airbnb.com
La Perla Cottage in Ogunquit, Maine

La Perla Cottage - Ogunquit

This little blue abode sits right on the Ogunquit river, which reflects the surrounding foliage when the season turns the leaves. Inside has been masterfully renovated, to be both contemporary but full of classic aesthetics. Exposed woodwork, subway tiling, polished fixtures – it’s absolutely magazine-worthy. The location is excellent, being near restaurants and shops.

Cottage with Ocean View, Lobster Boat Lounge - Machiasport Cottage/w ocean view, hiking + lobster boat lounge
Credit: Airbnb.com
Cottage/w ocean view, hiking + lobster boat lounge

Cottage with Ocean View, Lobster Boat Lounge - Machiasport

The super cute small cottage overlooks a nature reserve, so you have diverse native plants and wildlife to observe. The best part is the lobster boat lounge that sits closer to the water. You read that right! It’s an extremely unique feature that offers unparalleled glimpses of the area. Hiking trails weave through the nearby woods, and bucket list destinations like Acadia National Park are near.

Moosehead Hideaway - Northwest Piscataquis Moosehead Hideaway
Credit: VRBO.com
Moosehead Hideaway

Moosehead Hideaway - Northwest Piscataquis

This cozy rental is located right on Moosehead Lake. And there’s plenty of outdoor deck space to enjoy all of that gorgeous water and foliage. You could even sit on the dock, enjoying a hot cup of cider while wrapped in a blanket on a fall afternoon. Roast marshmallows over the fire pit, or hit the lake in a canoe for an up-close look of all the natural attributes.

Panoramic River Views - Walpole stunning, panoramic river views
Credit: VRBO.com
stunning, panoramic river views

Panoramic River Views - Walpole

Come to experience true old Maine on the Damariscotta River. Lobster boats and fishermen traverse the area and bring fresh seafood straight to the wharf. The cottage extends over the water and is breathtakingly scenic on a foggy morning. Especially when the leaves are changing. Inside is classic, pure and simple.

Lakeside Cottage in MidCoast Maine - Warren Lakeside Cottage in MidCoast Maine
Credit: VRBO.com
Lakeside Cottage in MidCoast Maine

Lakeside Cottage in MidCoast Maine - Warren

This little red cottage was made for fall staycations. Inside is constructed of polished wood, which is the perfect complement to all of the falling leaves. Enjoy the private lake, and sandy beach area, and soak in that cool breezy atmosphere. Being well under $200, this rental is a budget-friendly, yet still quite dreamy, autumn escape.

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