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.

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Top guest favourite

A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.

Earthen home in Sanford

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow 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.

4.92 out of 5 average rating, 132 reviews

Top guest favourite

A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.

Cabin in South Berwick

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

Top guest favourite

Place to stay in Shapleigh

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, 145 reviews

Top guest favourite

The exterior of the home is showcased at dusk, featuring large windows that reflect warm light. The two-story structure is framed by trees, with a deck visible on the upper level and stairs leading down to the ground. A serene natural setting surrounds the property.

Home in Shapleigh

Extraordinary Lakefront Retreat with Private Beach

This home we call “Loon Bluff” is a very special lakeside retreat. Beautifully furnished, the house boasts a chef’s kitchen, 2 living rooms with large TV’s, and comfortable beds. On the lake, you'll find a private sandy beach, watercraft, a kitchenette, and a large fire pit for cozy conversation. Loon Bluff is the perfect choice for those seeking the quintessential Maine lake experience while enjoying the comfort of a 5-star resort. Also available for weddings, film and television shoots.

5.0 out of 5 average rating, 71 reviews

Top guest favourite

Home in Limerick

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, 150 reviews

Top guest favourite

Cottage in Buxton

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

Top guest favourite

The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.

Home in Hollis

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, 510 reviews

Top guest favourite

The lakefront property is nestled among trees, showcasing a charming house with large windows and a deck. A private dock extends into the calm water, providing space for seating. A sandy beach area leads to the water's edge, creating a serene natural setting.

Home in Limerick

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

Top guest favourite

A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.

Chalet in Standish

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

Top guest favourite

The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.

Cabin in Freeport

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 reviews

Guest favourite

Cottage in Lyman

Cozy Waterfront Cottage w/ Private Dock & Kayaks

Waterfront getaway! Enjoy this cozy cottage year-round, set right on the pond with your own private dock for swimming and floating. Relax by the fireplace under twinkle lights or explore nearby trails for hiking, ATV, or snowmobiling. Take advantage of the kayaks and canoe, or unwind indoors with Smart TVs and DVDs. Just a short drive to Kennebunkport’s beaches, shops, and restaurants—perfect for a peaceful retreat.

4.83 out of 5 average rating, 121 reviews

Top guest favourite

Home in Waterboro

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.

5.0 out of 5 average rating, 65 reviews