Holiday rentals in Little Ossipee Pond

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.

Secluded Cabin: View, Hot Tub, 10 min Walk to Lake

Architect-designed alpine cabin with panoramic White Mountain views, including Mount Washington Relax in the hot tub, watch the sunset over the mountains, and enjoy a peaceful forest setting close to lakes, hiking trails, and skiing. 4WD or AWD REQUIRED Nov 1st-April 15th Starting May–Fall 2026, there may occasionally be (weekday only) construction noise up the road (250ft) from neighbors building their home. Work would occur roughly 8am–4/5pm and not every day. Cannot see it from the house.

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!

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!

Peaceful Cottage on Maine Flower Farm

Maine’s Peaceful Escape Nestled next door to Ferris Farm, our family-run flower farm, this charming cottage offers a private place to rest and recharge. Enjoy slow, coffee-filled mornings, quiet walks, and cozy evenings by the fire pit. Use the cottage as your home base to explore nearby beaches (30 minutes) or head into Portland (35 minutes) for breweries, coffee shops, and great dining. Perfect for a couple retreat, solo escape, or remote work getaway, with dedicated workspace.

Lakeside Serenity – Peaceful Maine Escape

Rejuvenate at our 3-bedroom lakeside retreat featuring queen beds, vaulted ceilings, lake-facing windows, and a spacious wraparound deck perfect for relaxing or dining outdoors. Cook with ease in the renovated kitchen with quartz countertops, island seating, and a new dishwasher. Enjoy a hammock, fire pit, outdoor grill, furnished deck, fast Wi-Fi, washer/dryer, three TVs, two double kayaks, and a canoe—everything you need for a peaceful, fun-filled escape on the lake!

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Peaceful 4 bedroom lakehouse retreat

Beautiful four bedroom two bath home located on Balch Lake in West Newfield Maine. Two private docks and your own boat launch. Sandy beach area on the south side of the house receives lots of sunshine. Take out kayaks or pedal boat to explore Balch Lake! Updated kitchen and a magnificent view of the lake from the living room. Relax in the shade under 2 motor canopies on the deck off of the master bedroom. Enjoy a barbeque and go for a swim at this hidden gem.

The Fish Bowl-Waterfront Tiny House

Escape to a one-of-a-kind lakefront tiny house on a 5-acre peninsula on beautiful Sokokis Lake. This waterfront getaway offers lake views, direct shoreline access and a dome skylight in Maine. * 5 acre peninsula on Sokokis Lake * Shared dock & swim raft & dockside seating * Kayaks & canoes * Fire pit * BBQ grill * Full bathroom * Kitchen * Eating area * Sleeping loft w/memory foam queen mattress * U-shaped couch folds into large bed * A/C * Free parking

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Owl’s Nest Cabin with Hot Tub Near Lake & Trails

Escape to Owl’s Nest, a private wooded cabin with a hot tub, direct trail access, and lake access just across the road. Relax in the hot tub after a day of kayaking, hiking, or exploring nearby ATV and snowmobile trails. This cozy retreat sleeps 5 with a king bed and bunk beds, and features an open living space, private deck with BBQ, fire pit, hammock, and horseshoe pitperfect for a quiet, year-round getaway.

Drakes Island Beach Front Breathtaking Property !

Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !