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
15 May - 17 May
In two months
26 June - 28 June
In three months
24 July - 26 July
In four months
21 Aug - 23 Aug

Our top choices for Winthrop holiday homes

Exterior

Charming Lakefront Home: Big Porches, Kayaks & Room to Gather

Charming Lakefront Home: Big Porches, 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$929
includes taxes & fees
3 May - 4 May
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (10 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is AU$299
includes taxes & fees
12 May - 13 May
Discover Oakland charm near Colby College 10 min
Property grounds

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, (21 reviews)
"Very quiet spot right on the lake, relatively easy to get to, close to town. Cabin is small, which was perfect for the two of us. "
United States
Stephanie P.
The price is AU$456
includes taxes & fees
7 May - 8 May
Cozy Cottage on water's edge of Lake Cobbosseecontee
Interior

Island Tree House Glamping

Island Tree House Glamping
Monmouth
10.0 out of 10, Exceptional, (9 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$458
includes taxes & fees
3 May - 4 May
Island Tree House Glamping
Exterior

Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway

Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Very accommodating host. Loved everything about it. Highly recommend "
United States
Mike M.
The price is AU$459
includes taxes & fees
30 Apr - 1 May
Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway
3 bedrooms, desk, iron/ironing board, free WiFi

An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (66 reviews)
"Very nice and comfortable house, clean and quiet. The hosts were very responsive. We had a great stay."
United States
Jessica Stebbins B.
The price is AU$284
includes taxes & fees
4 May - 5 May
An Authentic Clean & Cozy Maine Homestay
Terrace/patio

Hammock Haven Island Dome

Hammock Haven Island Dome
Monmouth
10.0 out of 10, Exceptional, (3 reviews)
"Could not have asked for a better way to end our vacation than a visit to this island. For being a sustainable space it does not lack in amenities conducive to comfort, and the setting is pristine. I had particular fondness for the rope swing!!"
United States
BlairR
The price is AU$285
includes taxes & fees
4 May - 5 May
Hammock Haven Island Dome
Property grounds

Island Tent Overlook in Maine

Island Tent Overlook in Maine
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 AU$332
includes taxes & fees
3 May - 4 May
Island Tent Overlook in Maine
Property grounds

Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (8 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$366
includes taxes & fees
4 May - 5 May
Floating Island Cabin
Exterior detail

Peaceful Home in Central Maine

Peaceful Home in Central Maine
Sidney
9.0 out of 10, Wonderful, (7 reviews)
"nice house just as advertised, very comfortable beds, communication with host was excellent, no surprises. House was only 6 minutes from boat ramp of Messalonskee Lake where we went ice fishing. Great year-round destination house!"
United States
Darren
The price is AU$583
includes taxes & fees
30 Apr - 1 May
Peaceful Home in Central Maine
Microwave, oven, stovetop, dishwasher

Spacious 4-bedroom house with chef's kitchen - Historic Belgrade Village

Spacious 4-bedroom house with chef's kitchen - Historic Belgrade Village
Belgrade
10.0 out of 10, Exceptional, (1 review)
"Really enjoyed everything about this home. Would recommend to anyone looking to visit the Belgrade Lakes area."
United States
Ken S.
Spacious 4-bedroom house with chef's kitchen - Historic Belgrade Village
Terrace/patio

Naughty Dog Private Island Log Cabin

Naughty Dog Private Island Log Cabin
Monmouth
10.0 out of 10, Exceptional, (11 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$643
includes taxes & fees
3 May - 4 May
Naughty Dog Private Island Log Cabin
Room

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$367
includes taxes & fees
17 May - 18 May
Beautifully remodeled first floor of a duplex home, surrounded by privacy fence
Interior

Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes
Litchfield
10.0 out of 10, Exceptional, (13 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$534
includes taxes & fees
30 Apr - 1 May
Camp Lintonia on Tacoma Lakes
Terrace/patio

Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!

Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
Wales
8.8 out of 10, Excellent, (5 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$1,001
includes taxes & fees
25 May - 26 May
Lakefront Log Cabin Getaway on Sabattus Pond - Dog Friendly!
TV, books, offices, printers

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$1,397
includes taxes & fees
3 May - 4 May
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Property grounds

Eco-Island Events: Weddings, Families, Retreats

Eco-Island Events: Weddings, Families, Retreats
Monmouth
The price is AU$2,057
includes taxes & fees
7 May - 8 May
Eco-Island Events: Weddings, Families, Retreats
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

Hilton Garden Inn Auburn Riverwatch

Hilton Garden Inn Auburn Riverwatch

10/10 Excellent
"Very clean accommodation and the staff was friendly and helpful"
Scott 2-night trip
Posted 5 hours ago
Hilton Garden Inn Auburn Riverwatch

Find out more about Winthrop

Winthrop Holiday Homes information

Number of reviews
106
Accommodation
142 Holiday Homes
Lowest Price
AU$284
Highest Price
AU$2,057