
Holiday rentals in Little Ossipee Pond
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Top-rated holiday rentals in Little Ossipee Pond
Guests agree: these stays are highly rated for location, cleanliness and more.

Romantic A-Frame cabin in the woods
Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.
5.0 out of 5 average rating, 325 reviews
Secluded Coastal Home & Cottage 3 Minutes to Beach
Escape to Thistle Pond Cottage, a peaceful coastal retreat in southern Maine. Nestled on 2 acres with pond views, lush gardens, and local wildlife, it’s minutes from beaches and Portland. Every stay begins with homemade bread from our kitchen and thoughtful, locally sourced welcome accompaniments. Weather and seasonal permitting, guests may occasionally savor a host-prepared wood-fired pizza made with fresh garden ingredients. Cozy, bright, and full of garden-to-table charm and seasonal delight.
5.0 out of 5 average rating, 107 reviews
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.
4.91 out of 5 average rating, 604 reviews
Historic Schoolhouse c1866 + Pool + Lake + Hot tub
Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.
5.0 out of 5 average rating, 144 reviews
Lakefront Getaway
Looking for a quiet peaceful getaway? Our Maine post and beam home is set on 7 acres of lake front. Great getaway to enjoy marshmallows and a roaring fire, kayaking, canoeing, swimming, boating or enjoy a great movie. For downhill skiers proximity to King Pine, Sunday River, Shawnee Peak and Black Mountain. Cross country and snow shoeing on property and on the lake. If you have a snow mobile- great trails available. Finally, great shopping in nearby North Conway at the outlets.
4.93 out of 5 average rating, 149 reviews
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!
4.98 out of 5 average rating, 200 reviews
The Copper Fox Treehouse
Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse
4.99 out of 5 average rating, 198 reviews
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.
4.97 out of 5 average rating, 187 reviews
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.
4.99 out of 5 average rating, 507 reviews
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.
5.0 out of 5 average rating, 142 reviews
Blueberry Hill
Beautiful property located on Watchic Lake in Standish Maine. Clear clean spring fed lake. 25 minutes to Portland with access to shopping, restaurants and entertainment. 45 minutes to North Conway New Hampshire. Where you wil find plenty of shopping, restaurants and winter skiing. Property includes use of Main Chalet home year round and two additional cabins each sleeping 4 are available from May-Oct. Great for extended families and friends.
4.96 out of 5 average rating, 263 reviews
The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.
5.0 out of 5 average rating, 155 reviewsPopular amenities for Little Ossipee Pond holiday rentals
Other great holiday rentals in Little Ossipee Pond

Owl’s Nest Cabin with Hot Tub Near Lake & Trails
5.0 out of 5 average rating, 65 reviews
Extraordinary Lakefront Retreat with Private Beach
5.0 out of 5 average rating, 70 reviews
Peaceful and Rustic Lakeside Cabin
5.0 out of 5 average rating, 91 reviews
Mountain View Getaway 4Season Maine
4.94 out of 5 average rating, 16 reviews
The Getaway at Lake Arrowhead
5.0 out of 5 average rating, 16 reviews
Eagle Island on Wadleigh Pond
4.89 out of 5 average rating, 65 reviews
Mermaid's Chair | Private Beach | Hot Tub
4.95 out of 5 average rating, 19 reviews
5 Acre Lakefront Getaway
5.0 out of 5 average rating, 15 reviewsDestinations to explore
- Sebago Lake
- Ogunquit Beach
- Hampton Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Short Sands Beach
- Willard Beach
- York Harbor Beach
- North Hampton Beach
- Scarborough Beach
- Cape Neddick Beach
- Footbridge Beach
- Jenness Beach
- Cranmore Mountain Resort
- Hills Beach
- Gooch's Beach
- East End Beach
- Fortunes Rocks Beach
- Wallis Sands Beach
- Pleasant Mountain Ski Area





