Vacation rentals in Little Ossipee Pond

4.9 out of 5 average rating, 521 reviews

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

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.

4.83 out of 5 average rating, 103 reviews

A sunlit sunroom features a mix of comfortable seating, including a sectional sofa and two chairs, arranged around a wooden coffee table. Large windows allow natural light to fill the space, providing views of the surrounding greenery and seasonal foliage.

Cottage in Lyman

RK North : All season Waterfront cottage with dock

Waterfront get away !You will love the cottage in any season - right on the pond! Enjoy a private dock, swimming and floating right at your door. Relax at the fireplace under twinkle lights , enjoy birdwatching, hiking and swimming during your stay. Lots of ATV and snowmobile trails near by. A close drive to Kennebunkport where your find beach’s , shops and restaurants galore. The cottage has 2 kayaks and a canoe for use during your stay. There are 2 Smart TVs for streaming. Shows and DVD

5 out of 5 average rating, 112 reviews

The exterior of a newly built guesthouse is displayed against a clear sky, showcasing modern architecture with a dark grey facade and a sloped metal roof. Snow covers the ground, while trees border the property, suggesting a peaceful rural setting.

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!

4.96 out of 5 average rating, 158 reviews

A serene view of the beach at sunset is framed by pine branches. The sandy path leads toward the water, where the calming waves reflect hues of orange and blue. Grassy dunes softly line the walkway, adding to the peaceful atmosphere.

Guest suite in Saco

LunaSea Suite

Be our guests and enjoy this dreamy, romantic little getaway and all that Saco and surrounding areas have to offer! Direct access to the River Walk. Short 5 minute walk to downtown Saco, Amtrak station, and 10 minute walk to downtown Biddeford. Visit our amazing shops, breweries, restaurants and cafes! Bayview Beach 3 miles OOB Pier 4.4 miles Private entrance and deck with outside fireplace. Hosts, Melissa and Doug, are quiet and considerate early risers with 2 friendly pups

4.96 out of 5 average rating, 236 reviews

A chicken perches comfortably on a shoulder, showcasing its rich golden feathers. The rustic wooden structure provides a warm backdrop, with natural light highlighting the textures of the wood and the bird's features.

Farm stay in Buxton

Little River Flower Farm - Cottage

Post & Beam Cottage, rustic knotty pine interior. Five miles to Gorham Center close to USM, 20 minutes to St. Josephs College on Sebago Lake, easy 30 minute drive to Portland, 12 miles to the PWM Jetport. Centrally located to many of Maine's finest breweries: Sebago Brewing, Mast Landing, Funky Bow, Nonsuch, Sea Dog, Barrel Souls, Bissell Brothers. Many local hiking trails including trails right here at our farm. Portland boasts of the finest restaurants in the state.

4.97 out of 5 average rating, 145 reviews

A vase filled with pink tulips sits on a rustic wooden table. Natural light pours in through a window, highlighting the fresh blooms and the texture of the table. The backdrop features soft, muted colors from the cottage's interior.

Cottage in Buxton

Peaceful Cottage on Maine Flower Farm

Overlooking vibrant flower fields at Ferris Farm, this charming cottage offers a peaceful retreat to relax and reconnect with nature. Wake up to scenic views, sip coffee on the deck, and explore the farm before spending the afternoon kayaking the Saco River. Use the cottage as a home base to visit Old Orchard and Saco beaches or experience Portland’s craft breweries, coffee shops, and incredible dining. Ideal for a solo retreat, romantic escape, or remote work getaway.

5 out of 5 average rating, 206 reviews

A modern cabin with a distinctive A-frame design showcases warm lighting along its edges. Two Adirondack chairs are positioned outside, with a wood stack nearby. A sauna is visible in the background, surrounded by lush greenery and soft outdoor lighting.

Cabin in South Berwick

Romantic A-Frame cabin in the woods

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.

4.99 out of 5 average rating, 250 reviews

A gentle green landscape is viewed from two white Adirondack chairs positioned on the grass. A wooden fence runs through the scene, surrounded by trees that provide ample foliage. The sky is clear and bright, enhancing the tranquil setting.

Cottage in Brownfield

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

4.93 out of 5 average rating, 105 reviews

The image captures a serene river scene, where gentle rapids flow over rocks, surrounded by lush greenery. Bright blue skies and soft white clouds enhance the tranquil atmosphere. The vibrant foliage adds natural beauty to the landscape, creating a peaceful outdoor space.

Guest suite in Standish

Steep Falls Escape, river & falls just steps away

Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.

4.99 out of 5 average rating, 429 reviews

A welcoming entrance features a covered porch with two blue chairs. Snow blankets the ground around the path leading to the door, while wooden siding and large windows hint at the warm atmosphere inside.

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.

5 out of 5 average rating, 104 reviews

A modern cabin with a black exterior is surrounded by a serene winter landscape, featuring snow-covered trees and a blanket of snow on the ground. A wooden deck extends from the cabin, blending with the natural surroundings in this peaceful winter setting.

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.

Apartment in Hollis Center

A glass dish shaped like a duck holds several eggs on a colorful tablecloth featuring various patterns. The soft, muted colors of the eggs contrast with the vibrant design of the fabric underneath.

4.83 out of 5 average rating, 335 reviews

Lily Brook Farm, Hollis, Maine

One bedroom apartment on horse/sheep farm in Hollis, Maine. View of farm from living room, bedroom on second floor up very steep farm stairs. One Queen comfy bed. There is a day bed in the living room. 21 miles from Portland and Kennebunkport. The farm is on rt 35. Cars can go by fast, they always break the speed limit. Lots of peace out the back door but be aware this is not way out back away from the road.

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Other great vacation rentals in Little Ossipee Pond

A wooden sign marks the entrance to Crescent Beach State Park. The sign features clear lettering indicating the park's name and its location in Cape Elizabeth, with surrounding greenery and an open road visible in the background.

Apartment in Waterboro

4.84 out of 5 average rating, 135 reviews

Our Cozy Stay

ChristopherRating, 5 stars3 weeks ago

Angie was a great host. We really appreciate her accommodating us and our 1 year old daughters.

4.93 out of 5 average rating, 15 reviews

An inviting camper interior features a plush dark leather sofa with decorative pillows, creating a comfortable seating area. A light marble table is surrounded by cushioned seating, and large windows provide ample natural light, enhancing the spacious feel of the living space.

Camper/RV in Buxton

Farm stay

SharonRating, 5 stars8 months ago

If you're looking for a beautiful rustic place to stay in Maine and get away from the city and its light pollution, I highly recommend Stephanie's listing! Being surrounded by trees, the sounds of farm animals, and the stars at night was so lovely. Stephanie was friendly and also prompt with replying. I would definitely stay here again if I came back up to Maine, esp at the price point.

4.97 out of 5 average rating, 36 reviews

A red barn-style house is set against a clear blue sky, with green grass surrounding it. A wooden deck area is visible in the foreground, featuring a pergola structure. Trees are scattered in the background, maintaining a sense of privacy and tranquility.

Vacation home in Cornish

Charming mountain retreat with endless views

NikitaRating, 5 stars3 days ago

Scott’s place is even more beautiful than the pictures posted. You can see beautiful views from the kitchen and both bedrooms. What a peaceful place. The only regret is we didn’t stay there enough. 2 days wasn’t enough to soak in it’s beauty. We decided to eat one meal there. They made pasta from scratch. It was delish. Homemade cookie was cherry on top. They also have all the kitchen and bathroom supplies you can probably think of. If we ever come to maine again, we will without a doubt book this place again. We have stayed in a lot of air bnb’s, this is the best so far. From a beautiful setting, to spacious rooms, to amenities to very warm hosts.

4.92 out of 5 average rating, 25 reviews

The exterior of a two-story lakeside unit is shown, featuring a covered patio with outdoor seating and an umbrella. A fire pit emits a warm glow, and a grill is positioned nearby. Lush greenery surrounds the property, creating a peaceful setting.

Guest suite in Lyman

Quaint 1-Bedroom Lakeside Unit On Bunganut Lake!

JamesRating, 5 stars8 months ago

Conor's lakeside cabin was a lovely place to stay. Private, quiet, beautiful, I highly recommend for a weekend or week away. It is well off the road, the instructions to get there were very clear and Conor was very responsive which is excellent. We will certainly be staying here again!

5 out of 5 average rating, 7 reviews

Three turquoise Adirondack chairs are positioned on the grassy bank of Pickerel Pond, facing the calm water. Sunlight filters through the trees, creating a serene outdoor setting, with gentle ripples on the surface of the pond reflecting the blue sky and clouds.

Home in Limerick

Cottage on Pickerel Pond

JennaRating, 5 stars9 months ago

We had a great time. Got to kayak around the pond several times. The jet skis and other motor boats and the gravel place were a little loud at times. That was my only complaint.

4.8 out of 5 average rating, 40 reviews

The cottage is nestled among lush greenery, featuring a white exterior and a quaint arched window. Colorful flower boxes are displayed beneath the window, while a hammock and two wicker chairs invite relaxation outside. A wooden fence separates the space from the natural surroundings.

Tiny home in Waterboro

Enchanting Artist Retreat

HannahRating, 5 stars8 months ago

What a cute spot! Peaceful, nice touches/amenities and not far from the Portland area. Barb is a very responsive and accommodating host. Thank you!

An outdoor dining area is set up with a table and four chairs under a large umbrella. The patio overlooks the lake, with boats visible on the water. A grill and storage unit are positioned nearby, enhancing the outdoor experience.

Home in Waterboro

4.71 out of 5 average rating, 7 reviews

Scenic Little Ossipee Lake Retreat w/ Grill!

JoyceRating, 5 stars10 months ago

Beautiful area very close to the beach. Nice place to stay with lots of scenic views of the lake from the house. Very relaxing way to spend a vacation.