Holiday rentals in Naples

4.96 out of 5 average rating, 26 reviews

Cabin in Pleasantdale

HotTub, Game Room, LakeFront,Paddleboards & Kayaks

Follow us @anchorunwind **Paddleboards, Kayaks and life jackets will be available as of mid-June** Discover our retreat, designed for families and couples to escape the city and reconnect with nature. Enjoy nearby trails, winter skiing, or paddle boarding on a pristine lake—this getaway has it all. Our cozy lake house offers a peaceful escape, with the soothing sounds of a stream between Trickey Pond and Sebago Cove as your backdrop. The home sleeps up to 6 adults and 2 children comfortably.

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.

4.91 out of 5 average rating, 114 reviews

Chalet in Denmark

Relaxing A-Frame with Hot Tub and Lake Access

Escape the city and relax at Camp Merryweather. Our A-Frame is perfect for a romantic getaway or a family retreat with the kids and dogs welcome also! If you’re a work from home professional looking to escape your normal routine, we’ve got you covered! With a fully equipped work space and reliable high speed internet you can break free from the pressures of the city while still staying connected. Kayaks and hot tub provided! Come experience our slice of heaven for yourself, you won’t regret it!

4.98 out of 5 average rating, 163 reviews

Home in Pleasantdale

Kayak to the Causeway-50s cottage with modern vibe

Find out why the Maine life is the best life at Moonstone Cottage. Play on the shores of Long Lake, stroll the Naples Causeway, eat your way around Portland, and hike the mountains of western Maine before coming home to relax around the fire pit, lounge on the deck, and get a feel for the way life should be. Kayaks are waiting for you on the private association beach, or rent a boat from the marina to explore 40 miles of open water. Restaurants, live music, and the market are a short walk away.

4.95 out of 5 average rating, 107 reviews

Paradise in the Lakes Region

A spectacular, massive, state-of-the-art log cabin that's the perfect getaway for summer vacations (beaches, water-sports, cookouts, galore), fall gatherings (stunning scenery) & winter ski trips (only 25 minutes to Pleasant Mountain) with friends or family. With a chef's kitchen, two ovens, a large dining area, bedrooms for up to 12 (with two king beds), two living rooms, & tons of outdoor dining & relaxation space, there's no gathering this wonderful, warm, gorgeous home can't accommodate!

4.94 out of 5 average rating, 630 reviews

Loft in Bridgton

Tap House Loft~Sunny & Spacious, Private Hot Tub

Conveniently located in the heart of Downtown Bridgton, the Tap House Loft is ready for you, your friends and your family to enjoy! Walk to vibrant Main Street, Pondicherry Park, the Magic Lantern Theater, Highland Lake and all the downtown shops, gallerias and restaurants...or simply relax in the peace and quiet of our newly restored, historic warehouse. Located above the Sundown Lounge, this 900 sq ft space offers a large Master Suite with French Doors leading to a deck and hot tub.

4.95 out of 5 average rating, 22 reviews

Cozy Getaway w/ Boat Launch & Kayaks

**DAILY BOAT LAUNCH ACCESS: MEMORIAL DAY TO LABOR DAY ** *NO PETS* Welcome to The Cove! This seasonal rental has everything you’d need for the perfect getaway! Centrally located to so many attractions, with fun for EVERYONE! Private community boat launch & kayaks available. Bring your watercraft! Long days having fun in the sun can sometimes get messy, unwind in the clean and calming bathroom. Enjoy your morning coffee on the large deck. Spend nights by the fire. Make s’more memories!

4.99 out of 5 average rating, 267 reviews

Guest suite in Bridgton

Barn on Pleasant- walk to town-no cleaning fee

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this summer walking distance to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

5 out of 5 average rating, 112 reviews

Guest house in Hiram

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

4.94 out of 5 average rating, 138 reviews

Cabin in Bridgton

Writers Cabin in the Woods on Adams Pond

Nestled in the woods and on Adams Pond next to a small farm. The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a gorgeous mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board!

4.95 out of 5 average rating, 211 reviews

Home in Bridgton

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

Dreamy mountainside home with views of Mt Washington and the White Mountains! Boasting 4 bedrooms and 2 bathrooms, this house is perfect for large groups seeking easy access to Pleasant Mountain Ski Area, Long Lake, Sebago Lake, and Saco River, along with nearby mountain biking, hiking, and snowmobile trails. After a long day of adventure, enjoy a soak in our 6-person hot tub, fully equipped kitchen, fire burning wood stove, and a cozy living room with a large screen TV!

4.97 out of 5 average rating, 39 reviews

Home in Pleasantdale

House at Sunshine- Long Lake, 5 min from causeway

This property has an inviting beach area and prime location! We are located on Long Lake amongst a small group of cottages. A sandy common area and shallow swimming spot make our rental area ideal for swimmers of any ability. We are within walking distance to many great restaurants, an arcade, & shops. Wintering here is a blast with snowmobiling, ice fishing, skiing, indoor pool, & local restaurants nearby. We have the best spot for 4th of July firework viewing!

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Cottages

Quaint homes, peaceful surroundings

Popular amenities for Naples holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Naples

4.96 out of 5 average rating, 25 reviews

Cottage in Bridgton

Lake Front Cabin on Desirable Highland Lake

DougRating, 5 stars1 week ago

My wife and I stayed at John's place for a quick weekend trip but the house is large enough for several more with 5 additional beds plus some space in the living room for sleeping. Great location on the lake with amazing views and only about a mile and a half from downtown Bridgton with some shops and nice restaurants. The house was immaculate and had everything you need from kitchen accessories to towels to plenty of games and books. John was extremely responsive and I don't think I waited more than 30 minutes for the few back and forth messages we had. Definitely recommend!

5 out of 5 average rating, 27 reviews

Babbling Brook Bungalow

MauricioRating, 5 stars2 weeks ago

The house was super cozy and extremely clean and well maintained. Cold water wasn’t an issue at all and tap water was super clean. Fire pit was great for making s’mores! Location was great for hiking around lake sebago and pleasant mountain. A bit far from Portland but a pleasant drive on the way there.

4.95 out of 5 average rating, 42 reviews

Home in Bridgton

Stunning Bridgton Lake House with EV charger

LimorRating, 5 stars3 months ago

Beautiful and comfortable house in a lovely natural setting, five minutes from Pleasant Mountain, which we think is a wonderful family ski area. Marty was very kind and extremely helpful with all our questions and requests. We would love to return and experience other seasons here as well.

5 out of 5 average rating, 18 reviews

Flat in Bridgton

Cozy Downtown studio apartment

Booth RappaportRating, 5 stars3 weeks ago

Cozy place with modern updates. Clean and comfortable. Easy walk to downtown. Sam was very responsive.

4.86 out of 5 average rating, 43 reviews

Cabin in Poland

Cozy cabin on the lake with the loons

AlleighRating, 5 stars1 month ago

This cabin is one of the most wonderful places I have been. My partner and I stayed just under a week and we enjoyed every second! It was so peaceful and relaxing to be away in such a beautiful home in an amazing area!

5 out of 5 average rating, 25 reviews

Cabin in Sebago

Charming Cabin Tucked in the Woods

DanRating, 5 stars2 weeks ago

Great cabin! Very clean and more spacious than you would think due to the open layout on the first floor. A nice little yard for pets to explore. Mark was very responsive and helpful - Hopefully we will be back!

4.94 out of 5 average rating, 17 reviews

Maine Life Camp close to Naples Causeway!

JasonRating, 5 stars8 months ago

this was a great little place for us to stay. plenty if room for the five of us staying.quick little walk to private boat access,very peaceful and quiet location for relaxing. only a few miles to the naples causeway for groceries and amenities. would definitely recommend if planning trip to the area.