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

Holiday Homes in Winthrop

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winthrop holiday homes

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

1. Island Tree House Glamping

Island Tree House Glamping
Monmouth
10.0 out of 10, Exceptional, (11 reviews)
"Sunset/rise were so perfect, and we got a special appearance of a double rainbow during our stay!"
United States
Desiree L.
The price is NZ$420
includes taxes & fees
29 Oct - 30 Oct
Island Tree House Glamping
A wooden cabin with a porch, a rocking chair, and a table with a lantern.

2. Naughty Dog Private Island Log Cabin

Naughty Dog Private Island Log Cabin
Monmouth
10.0 out of 10, Exceptional, (13 reviews)
"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....
United States
Peter O.
The price is NZ$564
includes taxes & fees
3 Nov - 4 Nov
Naughty Dog Private Island Log Cabin
A living room with a stone wall, a flat-screen TV, a ceiling fan, a fireplace, a sofa, and a patterned rug.

3. Renovated Year-Round Lake Retreat on Annabessacook Lake

Renovated Year-Round Lake Retreat on Annabessacook Lake
Monmouth
The price is NZ$611
includes taxes & fees
2 Nov - 3 Nov
Renovated Year-Round Lake Retreat on Annabessacook Lake
A campfire setup by a calm lake with a forest in the background.

4. Every window has a spectacular lake view Low fees

Every window has a spectacular lake view Low fees
Wayne
9.8 out of 10, Exceptional, (53 reviews)
"Great host!"
United States
Christine Z.
The price is NZ$748
includes taxes & fees
9 Nov - 10 Nov
Every window has a spectacular lake view Low fees
A spacious log cabin interior with a large living area, a stone fireplace, and a staircase leading to an upper level.

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

Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Wayne
9.0 out of 10, Wonderful, (2 reviews)
"The property was very nice!"
United States
James D.
The price is NZ$1,737
includes taxes & fees
29 Oct - 30 Oct
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
A living room with a ceiling fan, two chairs, a sofa, a coffee table, and a patterned rug.

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

Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
Sabattus
The price is NZ$526
includes taxes & fees
4 Nov - 5 Nov
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
A bedroom with a bed, wooden ceiling, a window with blinds, a nightstand, and a framed picture on the wall.

7. An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (70 reviews)
"Host was very accommodating and helpful! Was a great space to stay and felt homey! In a good area with plenty of amenities nearby."
United States
Autumn M.
The price is NZ$353
includes taxes & fees
30 Oct - 31 Oct
An Authentic Clean & Cozy Maine Homestay
A large, two-story house with a well-lit front porch and multiple windows.

8. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is NZ$740
includes taxes & fees
1 Nov - 2 Nov
Elizabeth Cottage
A wooden deck with outdoor furniture, a large potted plant, and string lights.

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

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Oakland
10.0 out of 10, Exceptional, (18 reviews)
"We loved staying at the farm! My kids enjoyed meeting the horse and donkey on property. It was perfect for our family!"
United States
Shana S.
The price is NZ$561
includes taxes & fees
10 Nov - 11 Nov
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A room with a view of a backyard, a wooden cabinet, a white countertop, and a wicker basket.

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

Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit
Lewiston
10.0 out of 10, Exceptional, (2 reviews)
"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...
United States
Eric L.
The price is NZ$1,247
includes taxes & fees
28 Nov - 29 Nov
Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit
A house with a white front door, a wreath, and flower boxes on the windowsills.

11. Arden Cottage

Arden Cottage
Mount Vernon
The price is NZ$740
includes taxes & fees
1 Nov - 2 Nov
Arden Cottage
A living room with a view of a lake, a dining area with chairs, and a coffee table.

12. Winter Lakefront Escape, Ice Fishing & Skiing

Winter Lakefront Escape, Ice Fishing & Skiing
Turner
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay! The host was exceptional, the house was amazing and the spot on the pond was beautiful. It was perfect for celebrating our son's graduation with our extended family. Elena was a wonderful host and she thought of everything we would need. The house was exceptionally clean and well appointed. We would love to stay again!"
United States
John C.
The price is NZ$1,249
includes taxes & fees
16 Nov - 17 Nov
Winter Lakefront Escape, Ice Fishing & Skiing
A small, single-story house with a white exterior and a dark roof. It features a front door, two windows with shutters, and a small porch area.

13. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is NZ$740
includes taxes & fees
1 Nov - 2 Nov
Nightingale Cottage
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

14. A soul soothing escape. Artistically built and lovingly maintained.

A soul soothing escape. Artistically built and lovingly maintained.
New Sharon
10.0 out of 10, Exceptional, (31 reviews)
"Loved the cabin and the view!! Had a great stay, thank you to our host!! Would love to stay again "
United States
Matt W.
The price is NZ$672
includes taxes & fees
2 Nov - 3 Nov
A soul soothing escape. Artistically built and lovingly maintained.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winthrop Hotel Reviews

Hampton Inn Augusta

Hampton Inn Augusta

10/10 Excellent
"Great little hotel in Augusta, Maine. It's everything you would expect."
Elizabeth 1-night trip
Posted less than an hour ago
Hampton Inn Augusta

Find out more about Winthrop

Winthrop Holiday Homes information

Number of reviews
194
Accommodation
163 Holiday Homes
Lowest Price
NZ$353
Highest Price
NZ$1,737