Vacation rentals in Little Ossipee Pond

4.9 out of 5 average rating, 521 reviews

A wooden treehouse is nestled among tall trees in a tranquil forest setting. A spacious deck extends from the structure, overlooking the surrounding greenery. Below, a private hot tub is situated on a stone platform, enhancing the retreat's serene atmosphere.

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 large windows inviting natural light, overlooking the wooded surroundings. A cozy sectional sofa is complemented by a round coffee table and woven area rug. A decorative chandelier hangs above, and a wooden dresser adds modern charm to the space.

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 modern guesthouse is shown against a twilight sky, featuring a sleek exterior in muted grey tones. Snow blankets the ground around the structure, while the entrance displays wide glass doors and a spacious balcony above. Lush greenery is visible in the background.

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, 156 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

Suite LunaSea

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

4.97 out of 5 average rating, 144 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, 204 reviews

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

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.

4.93 out of 5 average rating, 104 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, 428 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, 102 reviews

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 out of 5 average rating, 103 reviews

A lofted bedroom features a spacious bed adorned with a vibrant striped blanket. Light filters through a window, highlighting the sloped whitewashed ceilings and simple artwork on the walls. Warm wood accents complement the soft, neutral tones throughout the room.

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, 334 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.

4.97 out of 5 average rating, 104 reviews

An infrared sauna is presented within a wooden interior, featuring a glass-enclosed design. The sauna is equipped with wooden benches and heart-shaped detailing on the interior walls. Natural light filters in through nearby windows, enhancing the relaxing atmosphere of the space.

Cabin in Newfield

The NEST Haven awaits you.

You found your ultimate relaxation spot, sandy beaches on Rock Haven Lake (only 800' from your front door) infrared Sauna (accessible through the secret door) , 3 person hot tub, outdoor (seasonal) shower, luscious king seize bed, 6' TIPI daybed, firepit, outdoor tipi swing, a balcony and deck to enjoy the peaceful neighborhood. Round shower and deep claw foot soaker tub. Enjoy, relax and let your soul ponder.

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Other great vacation rentals in Little Ossipee Pond

5 out of 5 average rating, 51 reviews

The A-Frame cabin is surrounded by trees, showcasing a modern design with a wooden exterior. Soft lighting enhances the structure's features, and large windows reflect the evening sky, creating a warm and inviting appearance at dusk.

Cabin in Freeport

The Maine Frame: Cozy Firepit 7 Min to L.L. Bean

PaigeRating, 5 stars1 week ago

Instructions on how to find were clear and prevented us from driving in circles due to incorrect location on gps. Cabin was easy to check in and clean. Location was perfect for our trip plans and provided great scenery! 10/10 recommend.

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.

4.96 out of 5 average rating, 24 reviews

Home in Lyman

Family Friendly Kennebunk Pond Lakefront Retreat

SharonRating, 5 stars6 days ago

This home served our family of 5 very well. It is a wonderful place if you like a beautiful lake view and easy access. The sound of the loons calling at night under a calm sky is very restful. The place has a warm, cabin feel with plenty of room to spread out and find your own space. Plenty of games and a great vinyl record collection and turntable make the evenings fun if you’re not down at the fire pit. We would stay 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.

4.86 out of 5 average rating, 21 reviews

A recreational vehicle is positioned among vibrant autumn foliage, with fallen leaves covering the ground. Red Adirondack chairs are arranged around a stone fire pit, featuring a grill in the background. The setting conveys a cozy outdoor atmosphere, surrounded by trees.

Camper/RV in Buxton

Beautiful sweet Autumn campsite near Saco River

JenniferRating, 5 stars6 days ago

Such a sweet little private spot. The camper is adorable and offers everything you need for a quiet retreat. Betsey is a wonderful host! Very responsive and available for any needs. Thank you Betsey!

5 out of 5 average rating, 62 reviews

A screened-in porch features wooden floors and walls, adorned with string lights overhead. A large picnic table with benches occupies the center, complemented by several lounge chairs. Views of the tree-lined shore of Lake Arrowhead are visible through the windows.

Cabin in Limerick

Peaceful and Rustic Lakeside Cabin

ShelbRating, 5 stars2 weeks ago

This spot was AMAZING, and Eva was such an incredible host. For a large party like mine, all of us felt comfortable, and there was more than enough space where we were not cramped in. The recommendations that Eva provided were accurate and very resourceful. I have reached out to her a few times to ask questions and extend my gratitude for being such an amazing host, and she was by far one of the friendliest hosts I have ever encountered. My family and I were disappointed that we needed to leave, but we will most definitely be coming back again next year!