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Our top choices for Winthrop vacation homes

1. 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 AED 257
AED 1,137 total
includes taxes & fees
5 Nov - 6 Nov
Naughty Dog Private Island Log Cabin

2. 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 AED 103
AED 853 total
includes taxes & fees
8 Nov - 9 Nov
Island Tree House Glamping

3. 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 AED 826
AED 1,501 total
includes taxes & fees
9 Nov - 10 Nov
Every window has a spectacular lake view Low fees

4. 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 AED 701
AED 1,220 total
includes taxes & fees
5 Nov - 6 Nov
Renovated Year-Round Lake Retreat on Annabessacook Lake

5. 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 AED 624
AED 1,137 total
includes taxes & fees
5 Nov - 6 Nov
Home Away From Home. Family friendly, comfortable- centrally located in Augusta

6. 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 AED 1,452
AED 3,564 total
includes taxes & fees
1 Dec - 2 Dec
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings

7. 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 AED 918
AED 1,085 total
includes taxes & fees
30 Nov - 1 Dec
Camp Lintonia on Tacoma Lakes

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 AED 624
AED 1,065 total
includes taxes & fees
5 Nov - 6 Nov
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence

9. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is AED 771
AED 1,519 total
includes taxes & fees
8 Nov - 9 Nov
Elizabeth Cottage

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 AED 456
AED 713 total
includes taxes & fees
6 Nov - 7 Nov
An Authentic Clean & Cozy Maine Homestay

11. 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 AED 868
AED 1,385 total
includes taxes & fees
5 Nov - 6 Nov
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

12. 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 AED 1,062
AED 2,558 total
includes taxes & fees
15 Nov - 16 Nov
Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit

13. 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 AED 1,121
AED 2,567 total
includes taxes & fees
16 Nov - 17 Nov
Winter Lakefront Escape, Ice Fishing & Skiing

14. Arden Cottage

Arden Cottage
Mount Vernon
The price is AED 771
AED 1,519 total
includes taxes & fees
8 Nov - 9 Nov
Arden Cottage

15. 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 AED 859
AED 1,377 total
includes taxes & fees
5 Nov - 6 Nov
A soul soothing escape. Artistically built and lovingly maintained.

16. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is AED 771
AED 1,519 total
includes taxes & fees
8 Nov - 9 Nov
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.

Learn more about Winthrop

Paddle across the pristine waters of Maranacook Lake, where summer visitors enjoy swimming, fishing, and lakeside picnics. Explore the charming downtown shops and cafes before heading to nearby Bailey Public Library for its local history collection.

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

Top reviews in Winthrop