
Holiday rentals in Winthrop
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Top-rated holiday rentals in Winthrop
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winthrop holiday rentals
Other great holiday rentals in Winthrop
Guest favourite

Home in Winthrop
5 out of 5 average rating, 5 reviewsWaterfront Lakehouse in Maine
Guest favourite

Cottage in Winthrop
5 out of 5 average rating, 8 reviewsElegant Cobbossee Lake cottage with dock
Guest favourite

Home in Monmouth
5 out of 5 average rating, 33 reviewsThe Cottage at Red Top - Cozy Lakeside Year-Round
Guest favourite

Cottage in Litchfield
4.91 out of 5 average rating, 22 reviewsLakeside Cottage Tacoma Lake

Cabin in Winthrop
5 out of 5 average rating, 5 reviewsFantastic 2BR Lakefront Dog Friendly | Dock
Top guest favourite

Tiny home in Winthrop
5 out of 5 average rating, 25 reviewsLakefront guest cottage,
Guest favourite

Home in West Gardiner
4.92 out of 5 average rating, 12 reviews3BR Retreat in West Gardiner

Cabin in Winthrop
5 out of 5 average rating, 3 reviewsCozy cabin in a very fun and convenient location.
Quick stats about holiday rentals in Winthrop
Total rentals
60 properties
Nightly prices starting at
₹3,418 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- China Holiday rentals
- Portland Holiday rentals
- Bar Harbor Holiday rentals
- Mid-Coast Holiday rentals
- Southern Maine Coast Holiday rentals
- Old Orchard Beach Holiday rentals
- Hudson Valley Holiday rentals
- Long Island Holiday rentals
- The Hamptons Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Waterfront rentals Winthrop
- Rentals with a kayak Winthrop
- Pet-friendly rentals Winthrop
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- Family-friendly rentals Winthrop
- Rentals with outdoor seating Winthrop
- Rentals with a patio Winthrop
- Rentals with lake access Winthrop
- Rentals with a washing machine and dryer Winthrop
- Rentals with a firepit Winthrop
- House rentals Winthrop
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- Sebago Lake
- Sunday River Resort
- Popham Beach State Park
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Samoset Resort
- East End Beach
- Belgrade Lakes Golf Club
- Cliff House Beach
- Pemaquid Point Lighthouse
- Sunday River Golf Club
- Portland Museum of Art
- Maine Maritime Museum
- Portland Country Club
- Wolfe's Neck Woods State Park
- Pinnacle Park
- Bradbury Mountain State Park
- Rockland Breakwater Light
- Eaton Mountain Ski Resort
- Lost Valley Ski Area
- Head Beach
- Pebbly Beach