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

Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winthrop vacation 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

July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Winthrop
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay"
United States
Michael Y.
The price is CA $448
CA $1,244 total
includes taxes & fees
Oct 1 - Oct 2
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
A wooden pathway leading to a body of water, surrounded by dense greenery.

2. Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly

Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
Monmouth
10.0 out of 10, Exceptional, (4 reviews)
"The island is great from the walking trails, amenities and great fishing. "
United States
Jeremy F.
The price is CA $50
CA $239 total
includes taxes & fees
Sep 10 - Sep 11
Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
A floating house with a glass door, a deck, and a table and chairs.

3. Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (9 reviews)
"What an absolute pleasure it was staying in the floating home on the island. It was everything we wanted it to be. We will make this an annual trip. "
United States
Carissa P.
The price is CA $72
CA $266 total
includes taxes & fees
Sep 10 - Sep 11
Floating Island Cabin
A wooden interior with a radial wooden ceiling design and a central skylight.

4. 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 CA $77
CA $386 total
includes taxes & fees
Sep 15 - Sep 16
Island Tree House Glamping
A room with a hexagonal glass ceiling, a bed with a plaid blanket, and a view of greenery outside.

5. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is CA $87
CA $277 total
includes taxes & fees
Sep 27 - Sep 28
Floating Island Dome - Pet-Friendly Lake Retreat
A wooden cabin with a porch, a rocking chair, and a table with a lantern.

6. 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 CA $192
CA $569 total
includes taxes & fees
Sep 20 - Sep 21
Naughty Dog Private Island Log Cabin
A covered deck with large windows overlooking a lake, a boat on the water, and a forested shoreline.

7. Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes
Litchfield
10.0 out of 10, Exceptional, (15 reviews)
"Amazing Host, beautiful place to stay with an awesome view, pleanty of room for everyone, all the amenities worked great and the showers had great pressure and were nice and hot! Definitely plan on renting this location in the summer! DEFINITELY a place to stay... solid 5 stars!!!"
United States
Meghan C.
The price is CA $482
CA $596 total
includes taxes & fees
Sep 22 - Sep 23
Camp Lintonia on Tacoma Lakes
A wooden deck with outdoor furniture, a large potted plant, and string lights.

8. 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, (16 reviews)
"Kathleen was a wonderful host. My family and I found the property welcoming and relaxing. Great place to stay if you are looking for a laid back atmosphere and peaceful time in the country."
United States
Jared
The price is CA $289
CA $594 total
includes taxes & fees
Sep 16 - Sep 17
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

9. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (16 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is CA $249
CA $426 total
includes taxes & fees
Sep 28 - Sep 29
Discover Oakland charm near Colby College 10 min
A house with a white front door, a wreath, and flower boxes on the windowsills.

10. Arden Cottage

Arden Cottage
Mount Vernon
The price is CA $289
CA $593 total
includes taxes & fees
Sep 13 - Sep 14
Arden Cottage
A spacious log cabin interior with a large living area, a stone fireplace, and a staircase leading to an upper level.

11. 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
10.0 out of 10, Exceptional, (1 review)
"The property was very nice!"
United States
James D.
The price is CA $602
CA $1,481 total
includes taxes & fees
Sep 14 - Sep 15
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
A covered patio with a view of a lake, outdoor furniture, and a wooden deck.

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

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
10.0 out of 10, Exceptional, (11 reviews)
"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!"
United States
Jennifer E.
The price is CA $486
CA $1,387 total
includes taxes & fees
Sep 23 - Sep 24
Family's Paradise: 3BR/2BA,Game Room & Lake Access
A large, two-story house with a well-lit front porch and multiple windows.

13. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is CA $289
CA $593 total
includes taxes & fees
Sep 13 - Sep 14
Elizabeth Cottage
A bedroom with a bed, wooden ceiling, a window with blinds, a nightstand, and a framed picture on the wall.

14. An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (68 reviews)
"This place is amazing! Quintessential Maine home experience!"
United States
Meagan D.
The price is CA $171
CA $277 total
includes taxes & fees
Sep 17 - Sep 18
An Authentic Clean & Cozy Maine Homestay
A wooden deck with outdoor furniture overlooking a body of water.

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

Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
Wales
9.0 out of 10, Wonderful, (8 reviews)
"Excellent log cabin right on the water. Property owners were great to deal with. Will stay again."
United States
Jared F.
The price is CA $483
CA $1,033 total
includes taxes & fees
Oct 4 - Oct 5
Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

16. 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, (30 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 CA $379
CA $616 total
includes taxes & fees
Oct 9 - Oct 10
A soul soothing escape. Artistically built and lovingly maintained.
A room with a view of a backyard, a wooden cabinet, a white countertop, and a wicker basket.

17. 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, (1 review)
"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 CA $398
CA $1,010 total
includes taxes & fees
Sep 22 - Sep 23
Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit
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.

18. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is CA $289
CA $593 total
includes taxes & fees
Sep 13 - Sep 14
Nightingale Cottage
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"Clean. Very nice pool. Quiet. Confortable beds. Good breakfast ´til 9h30 Sharp!"
Julie 1-night trip
Posted 4 hours ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Winthrop

Winthrop Vacation Homes information

Number of reviews
181
Accommodation
173 Vacation Homes
Lowest Price
CA $239
Highest Price
CA $1,481

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