Book Holiday Homes in Winthrop

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Winthrop

Whispering Waters Farmhouse/Barn

Whispering Waters Farmhouse/Barn

Buckfield
With a stay at this vacation home in Buckfield, you'll be on a lake, and 26.6 mi (42.8 km) from White Mountain National Forest and 29.9 mi (48.2 km) from Sebago ...
Whispering Waters Farmhouse/Barn
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Mount Vernon
With a stay at this vacation home in Mount Vernon, you'll be on the waterfront, and 5.1 mi (8.2 km) from Belgrade Lakes Chain and 6.5 mi (10.4 km) from Maranacook ...
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Augusta
Located in Augusta, this vacation home is on the waterfront, within a 15-minute drive of VA Maine Healthcare System - Togus and Old Fort Western.
Private and Calming Waterfront to the Rescue!
Save an average of 15% on thousands of hotels when you're signed in
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2 out of 5
Oakland
Located in Oakland, this vacation home is on the waterfront, a 1-minute drive from Belgrade Lakes Chain and 6 minutes from Tree Spirits.
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Manchester
Located in Manchester, this vacation home is on the waterfront, within a 15-minute drive of Cobbosseecontee Lake and Augusta Country Club.
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
The Modern Maine Retreat

The Modern Maine Retreat

Oakland
With a stay at this vacation home in Oakland, you'll be within a 5-minute drive of Belgrade Lakes Chain and Tree Spirits.
The Modern Maine Retreat
Brand New Waterfront Lake House (completed July 2021)

Brand New Waterfront Lake House (completed July 2021)

Belgrade
Located in Belgrade, this vacation home is on a lake, within a 15-minute drive of Belgrade Lakes Chain and Belgrade Lakes Golf.
Brand New Waterfront Lake House (completed July 2021)
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

Winthrop
Located in Winthrop, this vacation home is on the waterfront, a 1-minute drive from Annabessacook Lake and 7 minutes from Maranacook Lake.
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Charming 2-bedroom house in marvelous Auburn with AC, WiFi, and fenced yard.

Charming 2-bedroom house in marvelous Auburn with AC, WiFi, and fenced yard.

Auburn
Located in Auburn, this vacation home is within a 5-minute drive of Androscoggin Historical Society and Festival Plaza.
Charming 2-bedroom house in marvelous Auburn with AC, WiFi, and fenced yard.
Don't see what you're looking for?
See all available properties in Winthrop
View all properties
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.

Winthrop Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winthrop vacation homes are the perfect way for you to wing it.

Holiday houses in Winthrop let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winthrop in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winthrop adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winthrop with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winthrop vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winthrop Holiday Homes essential information

Accommodation
149 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Whispering Waters Farmhouse/Barn, Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting, Private and Calming Waterfront to the Rescue!, Beautiful lakeside 4 bedroom retreat with private dock and walkout basement, Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly, The Modern Maine Retreat, Brand New Waterfront Lake House (completed July 2021), Peaceful Fisherman's Paradise w/ Deck + Fire Pit!, Charming 2-bedroom house in marvelous Auburn with AC, WiFi, and fenced yard.

Top trending hotels in Winthrop

Dog Friendly Cabin Right On The Water!!!

Dog Friendly Cabin Right On The Water!!!

Winthrop
Located in Winthrop, this cabin is a 4-minute drive from Wilson Pond and 9 minutes from Mt Pisgah Conservation Area Trailhead.
Dog Friendly Cabin Right On The Water!!!
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Winthrop
Located in Winthrop, this vacation home is a 3-minute drive from Annabessacook Lake and 8 minutes from Maranacook Lake.
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Cottage on Cobbosseecontee Lake. Dates available.

Cottage on Cobbosseecontee Lake. Dates available.

Winthrop
Located in Winthrop, this cottage is on a lake, a 1-minute drive from Cobbosseecontee Lake and 9 minutes from Augusta Country Club.
Cottage on Cobbosseecontee Lake. Dates available.
Save an average of 15% on thousands of hotels when you're signed in
Escape to our cozy Winthrop cabin on Dexter Pond

Escape to our cozy Winthrop cabin on Dexter Pond

Winthrop
Located in Winthrop, this cabin is on a lake, within a 10-minute drive of Wilson Pond and Mt Pisgah Conservation Area Trailhead.
Escape to our cozy Winthrop cabin on Dexter Pond
Don't see what you're looking for?
See all available properties in Winthrop
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.