Search Cottages in Winthrop Harbor

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Compare 25 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, (58)
"I needed a place to stay for work. Thus lake house was well done! Cute, cozy and great views. The hosts were excellent and responded when needed. I will definitely be staying again when Im in the area!"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Lakefront Cottage with Gorgeous Sunsets
Terrace/patio

Lakefront Cottage with Gorgeous Sunsets

9.2 out of 10, Wonderful, (5)
"Simple, minimal, quaint cozy lake cottage with stunning views both day and night. Owner was very responsive and accommodating! Thanks for helping make our Christmas trip great."
Lakefront Cottage with Gorgeous Sunsets
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!
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
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
White House, Amazing Cottage, Lake Front, That Sleeps 34!
Exterior

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

9.0 out of 10, Wonderful, (8)
"There were 20 of us, 3 generations and this lakehome was perfect. Plenty of beds and space..never felt crowded and the bunk beds and little nooks were a hit with the little ones. House has everything you need and management was very responsive."
White House, Amazing Cottage, Lake Front, That Sleeps 34!
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
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
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!
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
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
Wisconsin Vacation Rental Retreat w/ Deck
Living area

Wisconsin Vacation Rental Retreat w/ Deck

3.0 star property
Wisconsin Vacation Rental Retreat w/ Deck
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
Lakefront cottage with gorgeous sunset views
Outdoor dining

Lakefront cottage with gorgeous sunset views

Lakefront cottage with gorgeous sunset views
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Living area

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
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
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!
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 Burlington Vacation Rental: Dock + Beach
Beach

Lakefront Burlington Vacation Rental: Dock + Beach

3.0 star property
Lakefront Burlington Vacation Rental: Dock + Beach
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!
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!
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.
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, (58)
"I needed a place to stay for work. Thus lake house was well done! Cute, cozy and great views. The hosts were excellent and responded when needed. I will definitely be staying again when Im in the area!"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
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, (232)
"I booked this property for a reunion with some old friends, with the intention that we would be spending a lot of time hanging out. This property was perfect for that -- lots of beds and bathrooms. A beautiful view of the lake from the main living area and two of the bedrooms. Lots of amenities/activities including a pool table, ping pong, a fire pit, etc. But perhaps the best feature was the openness of the kitchen/dining room/pool table/family room, which meant that you feel connected to...
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
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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