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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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 AU$1,233
includes taxes & fees
9 Sept - 10 Sept
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Interior

2. Island Tree House Glamping

Island Tree House Glamping
Monmouth
9.8 out of 10, Exceptional, (10 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 AU$430
includes taxes & fees
3 Sept - 4 Sept
Island Tree House Glamping
Property grounds

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 AU$332
includes taxes & fees
3 Sept - 4 Sept
Floating Island Cabin
Spa

4. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is AU$380
includes taxes & fees
23 Aug - 24 Aug
Floating Island Dome - Pet-Friendly Lake Retreat
Property grounds

5. The Little Grey Duck Cottage on Cobbossee Lake

The Little Grey Duck Cottage on Cobbossee Lake
Manchester
9.0 out of 10, Wonderful, (27 reviews)
"Location is amazing "
United States
Laura Q.
The price is AU$528
includes taxes & fees
11 Aug - 12 Aug
The Little Grey Duck Cottage on Cobbossee Lake
Terrace/patio

6. Naughty Dog Private Island Log Cabin

Naughty Dog Private Island Log Cabin
Monmouth
10.0 out of 10, Exceptional, (12 reviews)
"Our stay was amazing! The location was beyond what I expected. It was so peaceful and relaxing Kent the property owner was fabulous, anything we needed or wanted he brought to us. I highly recommend this property and we can’t wait to go back!"
United States
Anonymous traveller
The price is AU$689
includes taxes & fees
8 Sept - 9 Sept
Naughty Dog Private Island Log Cabin
Exterior

7. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (15 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is AU$304
includes taxes & fees
13 Aug - 14 Aug
Discover Oakland charm near Colby College 10 min
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 AU$595
includes taxes & fees
1 Sept - 2 Sept
Camp Lintonia on Tacoma Lakes
Living area

9. 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$404
includes taxes & fees
19 Aug - 20 Aug
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
TV, books, offices

10. 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 AU$1,559
includes taxes & fees
9 Sept - 10 Sept
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Exterior detail

11. Arden Cottage

Arden Cottage
Mount Vernon
The price is AU$601
includes taxes & fees
12 Aug - 13 Aug
Arden Cottage
3 bedrooms, desk, iron/ironing board, free WiFi

12. An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (68 reviews)
"My tenants said the accommodations were lovely "
United States
Nathan
The price is AU$290
includes taxes & fees
13 Aug - 14 Aug
An Authentic Clean & Cozy Maine Homestay
Outdoor dining

13. Peaceful retreat on farm minutes to lake. Bring kayak or canoe!

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Oakland
10.0 out of 10, Exceptional, (14 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
The price is AU$641
includes taxes & fees
12 Aug - 13 Aug
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Terrace/patio

14. 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)
"We enjoyed our stay."
United States
Tyson W.
The price is AU$1,712
includes taxes & fees
4 Sept - 5 Sept
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Exterior detail

15. Peaceful Home in Central Maine

Peaceful Home in Central Maine
Sidney
9.0 out of 10, Wonderful, (9 reviews)
"Had a great experience, host was super responsive and even accommodated us outside the parameters of their listing! House was super cute!! Highly recommend!!"
United States
Jessica G.
The price is AU$643
includes taxes & fees
23 Aug - 24 Aug
Peaceful Home in Central Maine
Interior

16. 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
The price is AU$987
includes taxes & fees
11 Aug - 12 Aug
Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit
Exterior

17. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is AU$601
includes taxes & fees
11 Aug - 12 Aug
Elizabeth Cottage
Terrace/patio

18. 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, (7 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 AU$979
includes taxes & fees
24 Aug - 25 Aug
Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
Interior

19. 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 AU$671
includes taxes & fees
6 Sept - 7 Sept
A soul soothing escape. Artistically built and lovingly maintained.
Exterior

20. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is AU$601
includes taxes & fees
11 Aug - 12 Aug
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
"We enjoyed our stay here. Alyssa at the front desk was really welcoming and helpful upon our arrival. Our room was clean and had everything we needed including a coffee maker, a large (dorm-sized) fridge with a REALLY good freezer, and a few toiletries. There was even a microwave in our room, although we did not need it. The beds were comfortable with tons of pillows. We were able to adjust the heat/cooling in the room and the curtain definitely blocked the light well. One thing I didn't notice when making the booking was that the hotel rooms are on outside hallways. We were two women traveling alone, but this was not a problem at all. We felt comfortable on the second floor. I am only mentioning it because I hadn't notice when I booked the room and wanted others to know it ahead of time. We had a nice dinner in the restaurant and there was live music, which was really fun. The bartender--I'm sorry I can't remember her name-- was very personable and excellent. For breakfast, we enjoyed the amazing spread downstairs. There was something for everyone. Speaking of that, there was a huge variety of people enjoying the hotel-- older folks, families with kids and families with teens. That speaks to how warm, welcoming and comfortable it was. Finally, the hotel was very easy to find, and there was ample parking."
Jennifer 1-night trip
Posted 5 hours ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Winthrop

Winthrop Holiday Homes information

Number of reviews
9,108
Accommodation
174 Holiday Homes
Lowest Price
AU$145
Highest Price
AU$292