Waterfront holiday rentals in Madison

Conway Farmhouse on Saco River

Set directly on the Saco River, this beautifully renovated farmhouse offers a peaceful escape surrounded by nature. Enjoy your morning coffee on the back deck or take the private stairs down to the water for swimming & floating. Just 10 minutes from North Conway, the home features a cozy fireplace, chef’s kitchen, spacious deck, & fire pit. The perfect home base for exploring the White Mountains, with a private setting ideal for families and groups to relax, reconnect, and make lasting memories.

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.

Elevated 4-Season home - Mtn Views +A/C + Firepit

Wake up to mountain views, sip coffee on the wrap-around deck, and breathe in the fresh Maine air. At Mountain View Lodge, every detail is designed for you to relax and recharge. Spend your days skiing at Pleasant Mountain, hiking local trails, or floating down the Saco River - and your evenings gathered around the firepit or curled up by the woodstove. With three bedrooms, two baths, and a fully equipped kitchen, there's space for families, friends, and couples to enjoy all four seasons.

N Conway 10 mi/Waterfront / Private Beach/fire pit

Peace comes dropping slow at this pond side chalet in Eidelweiss Village, an alpine oasis only 15 mins from North Conway. Here, on a private sandy beach, you can swim in calm waters; take a canoe or a kayak out for a leisurely row; toast marshmallows at a private fire pit and gaze up at a trillion stars in night skies unpolluted by urban glare. In the Winter months, you can ice skate on Little Pea Porridge Pond or go skiing at Pine King or Cranmore, or simply enjoy dinner with a view...

Conway Waterfront Base for Your Family Memories!

Waterfront gem in the middle of it all! Designed to be the ideal getaway regardless of the season. Beautiful views out master bedroom, the back porch and from the backyard year round. The feel of seclusion while still being near all activities! Enjoy the water on one of the two kayaks or in the 2 canoes. Perfect base for skiing, hikes and sightseeing! Easy drive to North Conway, Kankamangus Highway, White Mountains, Story Land and so much more! No need to leave the property, just enjoy!

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

RiverPine Retreat - Clean & Bright Waterfront Home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Waterfront, Wood stove & Private beach, Solo Stove

Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.

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.

Tall Pines Hideaway

Classic Maine cottage on Papoose Pond, nestled among the trees. Enjoy the peace and quiet of this small pond, whether reading a book, or paddling a kayak, canoe or paddleboard. All the equipment is waiting for you. Lots to explore in the area as well, being close to Bethel and Sunday River, Fryeburg, North Conway and the White Mountains. Enjoy the glow of the fire pit at night, or gather inside for games or a movie.

Waterfront Escape

Set just 20 feet from Pequawket Pond, this unique two-level cottage offers direct waterfront access in a quiet association. A spiral staircase leads to a lower-level bedroom with walk-out access, creating a distinct and private layout. Minutes from Mount Washington Valley, with easy access to skiing, hiking, and local shops. Guests also enjoy use of a kayak and two paddleboards for time on the water.

A luxury log apartment located on the Saco River

This exquisite log apartment offers a one of a kind luxury experience with a private master bedroom including a gas stone fire place, king bed with exquisite bedding and a balcony which overlooks a 140’ private beach on the Saco River. Also included is a fully equipped designer kitchen/living area with a queen sofa bed, a full spa-like bathroom with a steam shower, Kohler bidet, and soaking tub.