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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 29 Cottages in Winthrop Harbor with updated reviews, rates, and availability.

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Miscellaneous

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (69)
"What a cute, quaint cottage w/ a beautiful view. Property managers were great and place was very clean. I'd stay there again for sure. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
White House, Amazing Cottage, Lake Front, That Sleeps 34!
Beach nearby

White House, Amazing Cottage, Lake Front, That Sleeps 34!

9.2 out of 10, Wonderful, (9)
"We had an amazing stay with our family group of 30 people! The place is perfectly equipped for a large group, with plenty of kitchen utensils, beds, towels, sheets, and blankets—everything we needed for a comfortable stay. The view is absolutely breathtaking, and the area is so peaceful. We loved every moment and would highly recommend it to anyone looking for a great place for a big family gathering!"
White House, Amazing Cottage, Lake Front, That Sleeps 34!
A Diamond in the Rough
Sun loungers

A Diamond in the Rough

9.4 out of 10, Exceptional, (85)
"Very cosy & nice. The backyard was wonderful. We enjoyed the privacy. The location was convenient to restaurants, etc."
A Diamond in the Rough
Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports
Property grounds

Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports

9.6 out of 10, Exceptional, (19)
"Had everything we needed"
Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
TV, fireplace, books

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

3.0 star property
10.0 out of 10, Exceptional, (1)
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
The Lodge, Sweet Waterfront Cottage, Separate Unit
Beach nearby

The Lodge, Sweet Waterfront Cottage, Separate Unit

9.2 out of 10, Wonderful, (5)
"House is a duplex with common wall and deck area."
The Lodge, Sweet Waterfront Cottage, Separate Unit
Driftwood, Cozy Waterfront Cottage, Separate Unit
Beach nearby

Driftwood, Cozy Waterfront Cottage, Separate Unit

10.0 out of 10, Exceptional, (2)
"We loved everything about this property and it was perfect for our family vacation. This house was wonderfully stocked with everything we needed in the kitchen, bathroom, and bedrooms. We had a large group, but with the big backyard space that overlooked the lake, we fit very comfortably. Check in was easy and any questions I asked were answered promptly. We would highly recommend staying in this cute, updated home for your next lake getaway!"
Driftwood, Cozy Waterfront Cottage, Separate Unit
Lakefront Cottage with Gorgeous Sunsets
Pool

Lakefront Cottage with Gorgeous Sunsets

9.4 out of 10, Exceptional, (6)
"Beautiful area. Warm and cozy place."
Lakefront Cottage with Gorgeous Sunsets
Amazing summer lake escape in our waterfront cottage!!!
Exterior

Amazing summer lake escape in our waterfront cottage!!!

9.4 out of 10, Exceptional, (35)
"This is the 2nd time we rented this property and both times we had a great time . Kind of a quirky place with a mix of old and new. The grandkids loved a lot of the 50+ year old games. Hosts were easy to contact and replied quickly to any questions or concerns."
Amazing summer lake escape in our waterfront cottage!!!
Lakefront Home w/ Game Room, Theater & Dock!
Terrace/patio

Lakefront Home w/ Game Room, Theater & Dock!

3.0 star property
Lakefront Home w/ Game Room, Theater & Dock!
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Waterfront Fox Lake Vacation Rental w/ Fire Pit!
Terrace/patio

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

10.0 out of 10, Exceptional, (8)
"Homey and comfortable- the house had everything we needed with a nice, large kitchen. Everything was exactly as pictured. Right on the water with so much outdoor space! We had plenty of space to spread out inside-and the bar area and game room was a fun bonus. The sunsets were gorgeous and we enjoyed watching the eagles fly overhead. Close to shopping and restaurants. Would rent again!"
Waterfront Fox Lake Vacation Rental w/ Fire Pit!
Lakefront Antioch Home w/ Dock, Kayaks & Game Room
House (2 Bedrooms) | Interior

Lakefront Antioch Home w/ Dock, Kayaks & Game Room

3.0 star property
Lakefront Antioch Home w/ Dock, Kayaks & Game Room
Salem Vacation Home w/ Dock: Steps to Paddock Lake
House (4 Bedrooms) | Interior

Salem Vacation Home w/ Dock: Steps to Paddock Lake

3.0 star property
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Lakefront cottage with gorgeous sunset views
Property grounds

Lakefront cottage with gorgeous sunset views

Lakefront cottage with gorgeous sunset views
Wisconsin Vacation Rental Retreat w/ Deck
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, blender

Wisconsin Vacation Rental Retreat w/ Deck

3.0 star property
Wisconsin Vacation Rental Retreat w/ Deck
Lake Michigan Vacation Rental w/ Private Beach!
House (5 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Lake Michigan Vacation Rental w/ Private Beach!

3.0 star property
Lake Michigan Vacation Rental w/ Private Beach!
Lakefront Oasis w/ Boat Dock, Fire Pit, Grill
Outdoor dining

Lakefront Oasis w/ Boat Dock, Fire Pit, Grill

3.0 star property
Lakefront Oasis w/ Boat Dock, Fire Pit, Grill
Lakefront Antioch Cottage w/ Dock & Gas Grill!
Miscellaneous

Lakefront Antioch Cottage w/ Dock & Gas Grill!

10.0 out of 10, Exceptional, (2)
Lakefront Antioch Cottage w/ Dock & Gas Grill!
Waterfront Fox Lake Vacation Rental w/ Fire Pit!
Terrace/patio

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

3.0 star property
Waterfront Fox Lake Vacation Rental w/ Fire Pit!
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.
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Other property types in Winthrop Harbor

Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
Private kitchen

Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.

6.6 out of 10, (7)
"All features needed, it felt like being at home!!!"
The price is AED 624
AED 1,254 total
includes taxes & fees
5 May - 6 May
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
White House, Amazing Cottage, Lake Front, That Sleeps 34!
Beach nearby

White House, Amazing Cottage, Lake Front, That Sleeps 34!

9.2 out of 10, Wonderful, (9)
"We had an amazing stay with our family group of 30 people! The place is perfectly equipped for a large group, with plenty of kitchen utensils, beds, towels, sheets, and blankets—everything we needed for a comfortable stay. The view is absolutely breathtaking, and the area is so peaceful. We loved every moment and would highly recommend it to anyone looking for a great place for a big family gathering!"
White House, Amazing Cottage, Lake Front, That Sleeps 34!
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Miscellaneous

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (69)
"What a cute, quaint cottage w/ a beautiful view. Property managers were great and place was very clean. I'd stay there again for sure. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
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.