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

Holiday Homes in Winthrop

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winthrop holiday homes

A lakeside view with a sandy beach, trees, and a clear sky.

1. Renovated Year-Round Lake Retreat on Annabessacook Lake

Renovated Year-Round Lake Retreat on Annabessacook Lake
Monmouth
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay! The space was incredibly cozy, comfortable, and welcoming. Ryanne was an absolutely fantastic host. She was attentive, extremely responsive, and so accommodating throughout our stay. Her kindness and generosity really stood out, and she went above and beyond to make sure we had a great experience. The place was also thoughtfully stocked with so many toiletries and essentials, which was especially helpful since I had forgotten a few things of my own! It’s clear that...
United States
Elizabeth D.
The price is AU$517
includes taxes & fees
12 Nov - 13 Nov
Renovated Year-Round Lake Retreat on Annabessacook Lake
A cabin with a wooden deck overlooking a lake, surrounded by trees.

2. 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)
"The property was super clean, better than the description, and Tina was incredibly fast with responses to all our questions. I've used VRBO more than twenty times for week or two-week cabins stays and this was as easy and delightful as any of them!"
United States
Dan C.
The price is AU$578
includes taxes & fees
12 Nov - 13 Nov
Every window has a spectacular lake view Low fees
A wooden deck with a railing and steps leading to a house.

3. Home Away From Home. Family friendly, comfortable- centrally located in Augusta

Home Away From Home. Family friendly, comfortable- centrally located in Augusta
Augusta
The price is AU$388
includes taxes & fees
20 Nov - 21 Nov
Home Away From Home. Family friendly, comfortable- centrally located in Augusta
A cozy living room with a large window, a leather armchair, a beige sofa, and a wooden coffee table.

4. Readfield Retreat w/ Lake Maranacook Views!

Readfield Retreat w/ Lake Maranacook Views!
Readfield
9.4 out of 10, Exceptional, (16 reviews)
"Great spot for our family trip."
United States
Kevin P.
The price is AU$729
includes taxes & fees
12 Nov - 13 Nov
Readfield Retreat w/ Lake Maranacook Views!
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 AU$1,276
includes taxes & fees
16 Nov - 17 Nov
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
A covered deck with large windows overlooking a lake, a boat on the water, and a forested shoreline.

6. Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes
Litchfield
10.0 out of 10, Exceptional, (20 reviews)
"Loved it"
United States
Sandra R.
The price is AU$420
includes taxes & fees
10 Dec - 11 Dec
Camp Lintonia on Tacoma Lakes
A covered outdoor seating area with a view of a lake and trees.

7. Echo Lake Retreat: Dock, Kayaks, Sunsets

Echo Lake Retreat: Dock, Kayaks, Sunsets
Mount Vernon
The price is AU$833
includes taxes & fees
13 Nov - 14 Nov
Echo Lake Retreat: Dock, Kayaks, Sunsets
A living room with a ceiling fan, two chairs, a sofa, a coffee table, and a patterned rug.

8. 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 AU$417
includes taxes & fees
20 Nov - 21 Nov
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
A house with a white front door, a wreath, and flower boxes on the windowsills.

9. Arden Cottage

Arden Cottage
Mount Vernon
The price is AU$579
includes taxes & fees
16 Nov - 17 Nov
Arden Cottage
A bedroom with a bed, wooden ceiling, a window with blinds, a nightstand, and a framed picture on the wall.

10. 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 AU$318
includes taxes & fees
12 Nov - 13 Nov
An Authentic Clean & Cozy Maine Homestay
A lakeside park with a wooden deck, benches, and a clear view of the lake.

11. Private Lakefront Lodge - Sleeps 22 - 11 BR + Game Room, Sauna & Arcade

Private Lakefront Lodge - Sleeps 22 - 11 BR + Game Room, Sauna & Arcade
Litchfield
10.0 out of 10, Exceptional, (21 reviews)
"This was our second year staying here and we are so glad we did. The new owners have added some nice things like water coolers, updated dishes, glasses and silverware and wonderful towels. It made our stay even more enjoyable."
United States
Mary K.
The price is AU$2,004
includes taxes & fees
12 Nov - 13 Nov
Private Lakefront Lodge - Sleeps 22 - 11 BR + Game Room, Sauna & Arcade
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

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 AU$343
includes taxes & fees
16 Nov - 17 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.

13. 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 AU$983
includes taxes & fees
22 Nov - 23 Nov
Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit
A living room with a view of a lake, a dining area with chairs, and a coffee table.

14. 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 AU$1,016
includes taxes & fees
16 Nov - 17 Nov
Winter Lakefront Escape, Ice Fishing & Skiing
A cabin interior with a kitchen island, dining area, and a cozy seating space.

15. MoonLight Treehouse | Hot Tub · Lakefront Retreat

MoonLight Treehouse | Hot Tub · Lakefront Retreat
Belgrade
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful place."
United States
Steve M.
The price is AU$1,332
includes taxes & fees
14 Nov - 15 Nov
MoonLight Treehouse | Hot Tub · Lakefront Retreat
A large, two-story house with a well-lit front porch and multiple windows.

16. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is AU$593
includes taxes & fees
15 Nov - 16 Nov
Elizabeth Cottage
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.

17. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is AU$588
includes taxes & fees
15 Nov - 16 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.

18. 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 AU$539
includes taxes & fees
13 Nov - 14 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Hotel Reviews

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"The staff was exceptional in trying to help me deal with the On line agent with which i booked my room. the room was well appointed, clean and comfortable. Nothing to complain about here!"
jim 3-night trip
Posted 17 hours ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Winthrop

Winthrop Holiday Homes information

Number of reviews
239
Accommodation
160 Holiday Homes
Lowest Price
AU$318
Highest Price
AU$2,004