Winthrop Holiday House Rentals from AU$278: Search Holiday Homes

A wooden signpost with 'WINTHROP' written on it, surrounded by greenery and trees.

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Our top choices for Winthrop holiday homes

A two-story house with a red roof, located by a lake surrounded by dense green trees.

1. July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather

Winthrop

Michael Y.

includes taxes & fees

7 Oct - 8 Oct

A wooden interior with a radial wooden ceiling design and a central skylight.

2. Island Tree House Glamping

Monmouth

Desiree L.

includes taxes & fees

29 Sept - 30 Sept

A room with a hexagonal glass ceiling, a bed with a plaid blanket, and a view of greenery outside.

3. Floating Island Dome - Pet-Friendly Lake Retreat

Monmouth

includes taxes & fees

27 Sept - 28 Sept

A wooden cabin with a porch, a rocking chair, and a table with a lantern.

4. Naughty Dog Private Island Log Cabin

Monmouth

"Honestly, this property and the whole experience exceeded all my expectations (which were already pretty high). Kent and the team were so accommodating, making sure that we had everything that we needed and were available at any time. They made special plans to accommodate some friends for a day visit and were so kind and helpful. The property itself was so perfect for what we wanted and the dog so enjoyed the freedom that only a private island can bring! Thanks, Kent, for a very memorable stay....

Peter O.

includes taxes & fees

30 Sept - 1 Oct

A living room with a ceiling fan, two chairs, a sofa, a coffee table, and a patterned rug.

5. Beautifully remodeled first floor of a duplex home, surrounded by privacy fence

Sabattus

includes taxes & fees

26 Sept - 27 Sept

A covered deck with large windows overlooking a lake, a boat on the water, and a forested shoreline.

6. Camp Lintonia on Tacoma Lakes

Litchfield

Meghan C.

includes taxes & fees

30 Sept - 1 Oct

A spacious log cabin interior with a large living area, a stone fireplace, and a staircase leading to an upper level.

7. Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings

Wayne

James D.

includes taxes & fees

28 Sept - 29 Sept

A campsite with two wooden cabins, a dirt path, and string lights.

8. Old Apple Orchard Yurt 2

Buckfield

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a bed, wooden ceiling, a window with blinds, a nightstand, and a framed picture on the wall.

9. An Authentic Clean & Cozy Maine Homestay

Buckfield

Meagan D.

includes taxes & fees

29 Sept - 30 Sept

A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

10. Discover Oakland charm near Colby College 10 min

Oakland

Tammy W.

includes taxes & fees

24 Oct - 25 Oct

A large, two-story house with a well-lit front porch and multiple windows.

11. Elizabeth Cottage

Mount Vernon

includes taxes & fees

27 Sept - 28 Sept

A wooden deck with outdoor furniture, a large potted plant, and string lights.

12. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Oakland

Jared

includes taxes & fees

28 Sept - 29 Sept

A room with a view of a backyard, a wooden cabinet, a white countertop, and a wicker basket.

13. Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit

Lewiston

"We stayed here for a family event and the house was perfect for what we needed for our stay. The house was spotless, comfortable and there was plenty of room for us and the rooms were creatively themed. There were plenty of TVs and the pool was a big plus. The basement was a pleasant surprise, with the basketball and air hockey games, along with an exercise bike and TV. The neighborhood was quiet and safe. Our host John was very accommodating and quick to reply to messages. We would gladly stay...

Eric L.

includes taxes & fees

27 Sept - 28 Sept

A wooden deck with outdoor furniture overlooking a body of water.

14. Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!

Wales

Jared F.

includes taxes & fees

4 Oct - 5 Oct

A covered patio with a view of a lake, outdoor furniture, and a wooden deck.

15. Family's Paradise: 3BR/2BA,Game Room & Lake Access

Belgrade

"This property is so special! The setting is absolutely gorgeous and the home itself is perfect both inside and out. We stayed here for a college graduation and had multiple generations-the layout was terrific for all of us. We especially loved sitting by the lake, enjoying the views from the screened in porch, and family time in the game room. The communication from the host was excellent and the entire process from beginning to end was seamless. We hope to return for another stay!"

Jennifer E.

includes taxes & fees

26 Oct - 27 Oct