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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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 €798
includes taxes & fees
1 Sept - 2 Sept
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Spa

2. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is €230
includes taxes & fees
16 Aug - 17 Aug
Floating Island Dome - Pet-Friendly Lake Retreat
Interior

3. 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 €268
includes taxes & fees
3 Sept - 4 Sept
Island Tree House Glamping
Property grounds

4. Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee
Manchester
8.8 out of 10, Excellent, (25 reviews)
"Location is amazing "
United States
Laura Q.
The price is €334
includes taxes & fees
9 Aug - 10 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee
Terrace/patio

5. 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 €414
includes taxes & fees
3 Sept - 4 Sept
Naughty Dog Private Island Log Cabin
Smart TV, books

6. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (14 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is €185
includes taxes & fees
11 Aug - 12 Aug
Discover Oakland charm near Colby College 10 min
3 bedrooms, desk, iron/ironing board, free WiFi

7. 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 €192
includes taxes & fees
1 Sept - 2 Sept
An Authentic Clean & Cozy Maine Homestay
Living area

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 €248
includes taxes & fees
2 Sept - 3 Sept
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
TV, books, offices

9. 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 €988
includes taxes & fees
1 Sept - 2 Sept
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Exterior detail

10. Arden Cottage

Arden Cottage
Mount Vernon
The price is €378
includes taxes & fees
11 Aug - 12 Aug
Arden Cottage
Interior

11. 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 €378
includes taxes & fees
2 Sept - 3 Sept
Camp Lintonia on Tacoma Lakes
Outdoor dining

12. 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 €387
includes taxes & fees
12 Aug - 13 Aug
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Exterior detail

13. 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 €380
includes taxes & fees
9 Aug - 10 Aug
Peaceful Home in Central Maine
Interior

14. 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 €601
includes taxes & fees
2 Sept - 3 Sept
Pool, Dream Home Gym, TV+Desk in Each Room, 85" TV, Games, 2 BKB Hoops, Fire Pit
Terrace/patio

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, (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 €645
includes taxes & fees
2 Sept - 3 Sept
Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
Exterior

16. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is €378
includes taxes & fees
11 Aug - 12 Aug
Elizabeth Cottage
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 €390
includes taxes & fees
21 Aug - 22 Aug
A soul soothing escape. Artistically built and lovingly maintained.
Exterior

18. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is €385
includes taxes & fees
9 Aug - 10 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.
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

Hampton Inn Lewiston-Auburn

Hampton Inn Lewiston-Auburn

8/10 Good
"The room was clean and it was quiet."
Leanne 1-night trip
Posted 1 hour ago
Hampton Inn Lewiston-Auburn

Find out more about Winthrop

Winthrop Holiday Homes information

Number of reviews
210
Accommodation
176 Holiday Homes
Lowest Price
€185
Highest Price
€988