Book Holiday Homes in Winthrop
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Featured Holiday Homes in Winthrop

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.
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 |
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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. |
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Dog Friendly Cabin Right On The Water!!!

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

Cottage on Cobbosseecontee Lake. Dates available.

Escape to our cozy Winthrop cabin on Dexter Pond
More ways to explore Winthrop
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^Subject to availability and chosen travel dates.