Vacation rentals in Little Ossipee Pond

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Top-rated vacation rentals in Little Ossipee Pond

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Superhost

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

4.9 out of 5 average rating, 521 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.

Superhost

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

4.83 out of 5 average rating, 104 reviews

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

Guest favorite

A small, wooden dock extends into Jewett Pond, featuring two teal Adirondack chairs positioned towards the water. Lush green hills rise in the background, reflecting the serene setting. The calm water invites relaxation and offers unobstructed views of the surrounding nature.

Cabin in Waterford

4.89 out of 5 average rating, 152 reviews

Jewett Pond Retreat

Relax in the Western Maine Foothills at our cabin on Jewett Pond. The main cabin has 672 sq ft of finished living space with bedroom (queen bed), bathroom, basic kitchen, great room (queen sleeper sofa), and screened porch. There is an additional rustic bunkhouse with two twin beds. This space is ideal for a couple or adventurous family who enjoys swimming, canoeing, hiking, fishing, or sitting on the screened porch with a good book and pine forest backdrop. Canoe included with booking.

Top guest favorite

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

5 out of 5 average rating, 112 reviews

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!

Top guest favorite

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

4.96 out of 5 average rating, 158 reviews

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

Guest favorite

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

4.97 out of 5 average rating, 145 reviews

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.

Top guest favorite

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

5 out of 5 average rating, 206 reviews

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.

Top guest favorite

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

4.99 out of 5 average rating, 429 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.

Top guest favorite

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

5 out of 5 average rating, 105 reviews

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.

Top guest favorite

A charming storefront presents a colorful display with a large red sculpture and a vibrant flower garden. The shop window is adorned with playful designs and bright signage, while striped awnings provide shade over the entrance. Nearby buildings complement the quaint, inviting atmosphere.

Guest suite in South Portland

5 out of 5 average rating, 254 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

Guest favorite

A set of wooden stairs leads to a white door at the top. The stairs are surrounded by a gravel pathway and greenery, with a second door visible on the left side, featuring a seasonal wreath decoration.

Apartment in Saco

4.97 out of 5 average rating, 248 reviews

Cozy , pet friendly, quiet one bedroom studio

Take it easy at this unique and tranquil getaway. Cozy, sunny studio has everything you might need. Great place to rest and recharge in between beach trips, convenient shopping, exploring. It is a walking distance from Grocery store, Cozy breakfast restaurant, and more. Just minutes away from art galleries, coffee shops and bakeries. Wifi, Netflix, Kitchenette , parking! and even a friendly golden retriever Luna available for petting :)

Superhost

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.

Apartment in Hollis Center

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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Popular amenities for Little Ossipee Pond vacation rentals

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Pool

Free parking on premises

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Other great vacation rentals in Little Ossipee Pond

Top guest favorite

The exterior of the property is presented, featuring a charming two-story house with a peaked roof and wooden double doors. Large windows enhance the facade, surrounded by manicured grass and vibrant flower pots. A stone pathway leads to the entrance, framed by lush greenery.

Barn in Scarborough

5 out of 5 average rating, 17 reviews

Stunning 1 bedroom barn.

MariaRating, 5 stars7 months ago

I had a lovely stay at thr barn. Check in was smooth, space was very clean, the location was perfect. Lots of nature and beautiful park/trail at walking distance with a very quick drive to beach! Christopher and Nathalie are great hosts! They were responsive and also very accommodating with my needs. This is a wonderful Airbnb for a peaceful and serene nature retreat while also being close to Portland!

Guest favorite

A cozy cabin-style home with a sloped roof and a spacious deck is nestled among tall trees. The wooden exterior blends harmoniously with the natural surroundings. Steps lead up to the deck, which features chairs and large windows that enhance the inviting outdoor view.

Guest suite in Acton

4.82 out of 5 average rating, 34 reviews

Beautiful Lakefront Suite on Great East Lake

KelseyRating, 5 stars8 months ago

John was a lovely host, and the apartment was wonderful. The location was a great starting point from which to explore the surrounding area. Super peaceful, and the bed was so comfy. At night, you can see the stars through the skylights, which was great. The place had everything needed for a short stay, would definitely recommend!

Top guest favorite

The tiny house is softly illuminated by warm lights strung overhead, set against a serene nighttime forest backdrop. The cozy exterior features a welcoming entrance, with a picnic table and chairs arranged nearby under a shade umbrella, creating an inviting outdoor space.

Tiny home in Scarborough

4.97 out of 5 average rating, 39 reviews

Tiny Home Glamping Near Beach

Dave And ChrisRating, 5 stars4 days ago

Deno's tiny house was just the right space for us, with the addition of the bedroom next door to the main house. The beds were comfortable and the kitchen space was very workable and useful even for a small area. The layout worked well for us. It was great to have outdoor seating areas and a fire pit. The location was great too- a short drive to the ocean and restaurants, and Portland is an easy drive from Scarborough.

Top guest favorite

A screened-in porch features wooden beams and string lights, providing an inviting space. A view of lush green trees and the calm waters of Lake Arrowhead is visible through the screens, enhancing the connection to the natural surroundings.

Cabin in Limerick

5 out of 5 average rating, 62 reviews

Peaceful and Rustic Lakeside Cabin

ShelbRating, 5 stars3 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!

Top guest favorite

A bright great room features high wooden ceilings and large windows showcasing a scenic view. A cozy sofa in soft plum is complemented by natural wood accents and a round coffee table. A dining area with a sleek table is visible in the background.

Cabin in Norway

5 out of 5 average rating, 32 reviews

The Cloud Cabin

LilyRating, 5 stars1 day ago

Best Airbnb we have stayed in!! ❤️🤗 we can't wait to come back!

Guest favorite

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

4.8 out of 5 average rating, 41 reviews

Enchanting Artist Retreat

RodrigoRating, 5 stars4 days ago

Barb went above and beyond to make sure I felt well: she did laundry for me, she asked how I was when I was sick, she made very good breakfast every day.... She is an incredible host.

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.

Top guest favorite