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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 24 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.
Dining

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

10.0 out of 10, Exceptional, (63)
"Spotlessly clean. Great view of the lake and all of the ice fishermen. Perfect spot for the two of us. We will book again next time we are in town if available. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
White House, Amazing Cottage, Lake Front, That Sleeps 34!
Exterior

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!
Lakefront Cottage with Gorgeous Sunsets
Terrace/patio

Lakefront Cottage with Gorgeous Sunsets

9.4 out of 10, Exceptional, (6)
"Beautiful area. Warm and cozy place."
Lakefront Cottage with Gorgeous Sunsets
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Living area

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
A Diamond in the Rough
Morning sunrise

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
The Lodge, Sweet Waterfront Cottage, Separate Unit
Exterior

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
Waterfront Fox Lake Vacation Rental w/ Fire Pit!
Fox Lake Vacation Rental | 2BR | 1 Full BA | 2 Half BA | 5 Steps Required

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!
Hideaway at the Ponderosa- 3bd, 1Ba Country Cottage
Outside Front View

Hideaway at the Ponderosa- 3bd, 1Ba Country Cottage

9.4 out of 10, Exceptional, (12)
"Peaceful stay. It was just what we needed. "
Hideaway at the Ponderosa- 3bd, 1Ba Country Cottage
Driftwood, Cozy Waterfront Cottage, Separate Unit
Exterior

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 sunset views
Outdoor dining

Lakefront cottage with gorgeous sunset views

Lakefront cottage with gorgeous sunset views
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!
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Living area

Salem Vacation Home w/ Dock: Steps to Paddock Lake

3.0 star property
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Wisconsin Vacation Rental Retreat w/ Deck
Living area

Wisconsin Vacation Rental Retreat w/ Deck

3.0 star property
Wisconsin Vacation Rental Retreat w/ Deck
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Living area

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Lake Michigan Vacation Rental w/ Private Beach!
Dining

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
Exterior

Lakefront Oasis w/ Boat Dock, Fire Pit, Grill

3.0 star property
Lakefront Oasis w/ Boat Dock, Fire Pit, Grill
Lakefront Antioch Home w/ Dock, Kayaks & Game Room
Terrace/patio

Lakefront Antioch Home w/ Dock, Kayaks & Game Room

3.0 star property
Lakefront Antioch Home w/ Dock, Kayaks & Game Room
Waterfront Fox Lake Vacation Rental w/ Fire Pit!
Property grounds

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

3.0 star property
Waterfront Fox Lake Vacation Rental w/ Fire Pit!
Lakefront Antioch Cottage w/ Dock & Gas Grill!
Living area

Lakefront Antioch Cottage w/ Dock & Gas Grill!

3.0 star property
Lakefront Antioch Cottage w/ Dock & Gas Grill!
Lakefront Antioch Cottage w/ Dock & Gas Grill!
Antioch Vacation Rental | 3BR | 1BA | 900 Sq Ft | Stairs Required

Lakefront Antioch Cottage w/ Dock & Gas Grill!

10.0 out of 10, Exceptional, (2)
Lakefront Antioch Cottage w/ Dock & Gas Grill!
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.
Exterior

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!!!"
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
YOUR MORNING WAKE-UP CALL

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (233)
"This property is a TRUE GEM! The views and open-spaced layouts are amazing. The amenities are countless and plentiful; all that you'd want. No matter the season, this is a must stay. Everything was beautiful, clean, organized, well communicated, and just plain easy. A exemplary. Awesome Host. I will definitely be returning every year! "
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Dining

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

10.0 out of 10, Exceptional, (63)
"Spotlessly clean. Great view of the lake and all of the ice fishermen. Perfect spot for the two of us. We will book again next time we are in town if available. "
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.

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