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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winthrop holiday homes

Exterior

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 €780
includes taxes & fees
28 Sept - 29 Sept
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Property grounds

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 €155
includes taxes & fees
22 Sept - 23 Sept
Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
Property grounds

3. Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (10 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 €173
includes taxes & fees
21 Sept - 22 Sept
Floating Island Cabin
Interior

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 €231
includes taxes & fees
22 Sept - 23 Sept
Island Tree House Glamping
Spa

5. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is €171
includes taxes & fees
27 Sept - 28 Sept
Floating Island Dome - Pet-Friendly Lake Retreat
Terrace/patio

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 €347
includes taxes & fees
30 Sept - 1 Oct
Naughty Dog Private Island Log Cabin
TV, books, offices

7. 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 €919
includes taxes & fees
22 Sept - 23 Sept
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Interior

8. 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 €364
includes taxes & fees
21 Sept - 22 Sept
Camp Lintonia on Tacoma Lakes
3 bedrooms, desk, iron/ironing board, free WiFi

9. 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 €179
includes taxes & fees
21 Sept - 22 Sept
An Authentic Clean & Cozy Maine Homestay
Living area

10. 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
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
Exterior

11. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (17 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is €228
includes taxes & fees
20 Sept - 21 Sept
Discover Oakland charm near Colby College 10 min
Exterior detail

12. Arden Cottage

Arden Cottage
Mount Vernon
The price is €388
includes taxes & fees
20 Sept - 21 Sept
Arden Cottage
Outdoor dining

13. 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 €334
includes taxes & fees
21 Sept - 22 Sept
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Terrace/patio

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

Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
Wales
9.2 out of 10, Wonderful, (9 reviews)
"Excellent log cabin right on the water. Property owners were great to deal with. Will stay again."
United States
Jared F.
Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
Interior

15. 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 €645
includes taxes & fees
20 Sept - 21 Sept
Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit
Terrace/patio

16. 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.
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Interior

17. 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 €353
includes taxes & fees
29 Sept - 30 Sept
A soul soothing escape. Artistically built and lovingly maintained.
Exterior

18. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is €373
includes taxes & fees
29 Sept - 30 Sept
Elizabeth Cottage
Exterior

19. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is €388
includes taxes & fees
20 Sept - 21 Sept
Nightingale Cottage
Smart TV, fireplace, books

20. Loon Lodge on Locke Pond: Relax, Recharge and Explore

Loon Lodge on Locke Pond: Relax, Recharge and Explore
Chesterville
10.0 out of 10, Exceptional, (2 reviews)
"L’emplacement est parfait beaucoup de belle commodité intérieur et extérieur. Petit point négatif les lits ne sont pas faites et et doit les laver avant de partir."
Canada
Anny
The price is €388
includes taxes & fees
13 Oct - 14 Oct
Loon Lodge on Locke Pond: Relax, Recharge and Explore
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

SureStay by Best Western Lewiston Auburn Area

SureStay by Best Western Lewiston Auburn Area

10/10 Excellent
"We stayed for one night because we had an event to attend nearby. The place was clean and comfortable and the employees were friendly. :)"
Bobbi 1-night trip
Posted 3 hours ago
SureStay by Best Western Lewiston Auburn Area

Find out more about Winthrop

Winthrop Holiday Homes information

Number of reviews
181
Accommodation
169 Holiday Homes
Lowest Price
€171
Highest Price
€919