Holiday rentals in Little Ossipee Pond

4.9 out of 5 average rating, 521 reviews

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

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

Guest house 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, 157 reviews

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, 235 reviews

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

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, 205 reviews

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, 105 reviews

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

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

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.

4.83 out of 5 average rating, 334 reviews

Flat in Hollis Center

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, 105 reviews

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 holiday rentals in Little Ossipee Pond

Flat 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.

5 out of 5 average rating, 52 reviews

Cabin in Freeport

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

DennisRating, 5 stars2 days ago

Private and relaxing, I enjoyed really peaceful. The roster made so easy with all recommendations and resources we needed, me and my spouse loved it was really good experience “ we recommend”

4.81 out of 5 average rating, 58 reviews

Cabin in Cornish

Woodland Cabin by Saco River

KaraRating, 5 stars3 weeks ago

The hosts were so nice and able to get us this place very last minute! They were super understanding and helpful in giving good recommendations! Lots of hiking in the area and antique stores. Not far from Portland for a fun day trip! Loved hearing the rain come down on the roof too!

4.92 out of 5 average rating, 24 reviews

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

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, 7 reviews

Home in North Waterboro

Lake house on Lil Ossippee

AlishaRating, 5 stars9 months ago

We had a wonderful time at Jana’s place. It was right on the lake with lots of fish to catch right off the dock. There were kayaks, a canoe, paddle boards, a peddle boat, and plenty of fishing gear. It was dog friendly which made bringing our dogs so easy and enjoyable as they also loved the beauty of the location. Jana was helpful any time we needed her. The house was huge and the location was so serene. We stayed busy the entire trip and even drove a short half hour to old orchard beach. We will definitely be coming back with our daughter as there is a whole loft with lots to do for children. If you’re looking for a relaxing, peaceful, lakeside getaway with plenty to do Jana’s place is the place to go. I didn’t even use my phone hardly the entire trip because there was so much to do! We caught like 30 fish without even leaving the dock. The lake has perch and many other edible fish in it. The kitchen was fully stocked and we honestly felt right at home. Jana was friendly and helpful.

5 out of 5 average rating, 62 reviews

Cabin in Limerick

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!