Search Cottages in Winthrop

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Cottages in Winthrop

Lakefront Maine House ~ 4 Mi to Colby College

3.0 star property
Lakefront Maine House ~ 4 Mi to Colby College

Private Dock on Messalonskee Lake: Cozy Cottage!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
Private Dock on Messalonskee Lake: Cozy Cottage!

Readfield Retreat w/ Lake Maranacook Views!

3.0 star property
Readfield Retreat w/ Lake Maranacook Views!

Private Dock & Deck: Tranquil Dam Pond Cottage!

3.0 star property
Private Dock & Deck: Tranquil Dam Pond Cottage!

The Locke-ness Pond Cabin in Chesterville!

3.0 star property
The Locke-ness Pond Cabin in Chesterville!

Hartford Cottage w/ Private Beach on Bear Pond!

2.0 star property
8.8 out of 10, Excellent, (3)
"This was such a nice retreat. Beautiful views. Quiet comfortable getaway. It felt homey and inviting. I grew up going to a cottage like this and it was a blissful nostalgic weekend getaway right on the water. "
Hartford Cottage w/ Private Beach on Bear Pond!

Peaceful Lakefront Maine Cabin w/ Sunset Views

3.0 star property
Peaceful Lakefront Maine Cabin w/ Sunset Views

Waterfront Home w/ Boat Dock & Sunroom in Gardiner

3.0 star property
Waterfront Home w/ Boat Dock & Sunroom in Gardiner

Pet-friendly Togus Pond Home: Kayak & Canoe!

3.0 star property
Pet-friendly Togus Pond Home: Kayak & Canoe!

Lakefront Hartford Cabin w/ Canoe & Boat Ramp

3.0 star property
Lakefront Hartford Cabin w/ Canoe & Boat Ramp

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

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

Maine Cottage w/ Dock & Kayaks, Near Augusta!

3.0 star property
Maine Cottage w/ Dock & Kayaks, Near Augusta!

Life on the Lake With Private Dock & Fire Pit!

3.0 star property
Life on the Lake With Private Dock & Fire Pit!

Woodsy Pittston Retreat Near Kennebec River!

3.0 star property
Woodsy Pittston Retreat Near Kennebec River!

Annabessacook Lake Retreat w/ Deck: Pets Welcome!

3.0 star property
Annabessacook Lake Retreat w/ Deck: Pets Welcome!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winthrop Hotel Reviews

Frequently asked questions

Why book your cottage in Winthrop with Expedia?
We think a getaway should be a piece of cake, so if you're on the lookout for cottages in Winthrop at a nice price, Expedia has you covered. Keep the budget in check and opt for a cheap option surrounded by wilderness, or splurge on a luxury cottage to pamper your favourite people.
How can I find cheap cottages in Winthrop?
With Expedia's helpful filter tool, locating cheap cottages in Winthrop is a snap. To view accommodation that are friendly on the wallet, fine-tune your search results by star rating, budget and amenities.