Holiday houses in Brandy Pond

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, 44 reviews

Trickey Moose Family Retreat | Firepit Kayaks

Enjoy 4 seasons of fun with shared access to Trickey Pond and use of 2 kayaks, large deck, fire pit, gas grille, backyard, wood stove, air hockey, ping pong table, close to skiing, snowmobile trails, boating, hiking and much more. ** Summer Dates Still Available 6/23-6/27 6/30-7/3 7/6-7/9 8/17-8/22 Beautiful open concept house with loft and cathedral ceilings is perfect for large families with a well appointed kitchen, fast Wi-Fi, laptop friendly workspace, central AC, jacuzzi, free parking.

4.98 out of 5 average rating, 163 reviews

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, 108 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, 631 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.

4.99 out of 5 average rating, 268 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

Guesthouse 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!

4.93 out of 5 average rating, 154 reviews

Cabin in Raymond

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.

4.96 out of 5 average rating, 189 reviews

Guesthouse in Naples

Downtown Naples guesthouse. Steps from causeway

In the heart of Naples you will find this large 2 bedroom carriage house newly constructed in 2018, only steps away from the lakes, causeway, restaurants, grocery store and marinas. Each large bedroom has a queen bed, the kitchen is fully equipped, the television has Roku for cable access or streaming channels. There is a large deck overlooking a vacant lot. WIFI is included. Oxford Casino, Shawnee Peak, and Fryeburg Fairgrounds are all within half hour drive.

4.89 out of 5 average rating, 99 reviews

Cabin in Naples

Songo Lock Cabins #2

Cabins on the water, Songo Lock Cabins are located at the Historical Songo Locks. The cabins are over 100 years old and date back to the early 1900's. The cabins are on the water and have their own dock. The Songo Locks is hand operated and opens to allow boats into the lock, the water lowers the boats down and then opens so they can continue down river into Sebago Lake. You can sit at your cabin and watch the boats or grab a fish pole and do some fishing.

5 out of 5 average rating, 103 reviews

Home in Bridgton

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

5 out of 5 average rating, 3 reviews

Tiny home in Casco

The Casco Tiny house!

Nestled in the charming town of Casco, this cozy tiny house offers the perfect retreat for travelers and explorers seeking comfort and convenience. Located just off Poland Springs Road, you’ll enjoy effortless access to Maine’s many attractions while having a peaceful home base to relax. Whether you’re adventuring through the Pine Tree State or simply looking for a getaway, this tiny house is an ideal “home away from home” for your Maine journey.

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Other great holiday rentals in Brandy Pond

4.95 out of 5 average rating, 21 reviews

Long Lake Cottage

SusanRating, 5 stars1 week ago

Amanda’s place is super comfortable! Very pleasant, relaxing space, really comfy beds (although for a tall person they’re a bit short) and very clean, with luxurious towels and bedding. Beautiful mornings with coffee and birdsong on the screened in porch!

4.86 out of 5 average rating, 133 reviews

Cottage in Naples

Spring into Summer at Turtle Lane Cottage

JonathanRating, 5 stars1 week ago

My kids and I had a lovely time at Greg's place. It was very clean and comfortable, and plenty of space for cooking, eating, and lounging. We also enjoyed a turtle wandering through the yard. Only suggestion is to bring tissues and shampoo etc. for the shower - we had everything else we needed. Overall a very pleasant stay and we would definitely return!

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.

5 out of 5 average rating, 4 reviews

Cabin in Greenwood

Luxury Nordic Cabin | Lakefront w Hot Tub + Sauna

MarianRating, 5 stars3 months ago

An absolute gem if you want to reconnect with family/nature, relax and unplugg. It was so peaceful and tranquil. my 5 year old son loved being in the loft stargazing at night. we would be sitting in the deck by the firepit for smores and some snacks every night. Truly, one of our best family trips. Kendra is also very responsive.

5 out of 5 average rating, 16 reviews

Home in Raymond

Cozy Cottage on Big Sebago Lake

NancyRating, 5 stars2 weeks ago

This cottage is perfect for Sebago if you own a boat. She has everything you could need for a stay on the water. I would love to stay here again this year.

4.88 out of 5 average rating, 24 reviews

Cottage in Casco

Waterfront Getaway w/ Private Sandy Beach

RileyRating, 5 stars4 weeks ago

Perfect for what we needed for a weekend getaway. So peaceful and a lot of interesting wildlife. We saw so many different types of birds! The hot tub is spacious and easy to use.

5 out of 5 average rating, 64 reviews

Home in Sebago

Awesome Quiet Location near Sebago Lake Maine

AliciaRating, 5 stars8 months ago

This property is the perfect blend of lake house and a cabin in the woods. The kitchen is well-stocked with all the spices and pots & pans you might need. A grill, a fire pit, comfortable beds, and a cozy living room make it so easy to relax. Mo provides great recommendations for the Sebago Lake area and is very responsive. Highly recommend.