Vacation rentals in Winslow

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Top-rated vacation rentals in Winslow

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Galena

4.95 out of 5 average rating, 44 reviews

4bd/4ba Hot Tub/Fab Game Room/Wow Sunsets/Fire Pit!

North Star, Galena IL Entire Home Vacation Rental, 4 Bed, 4 Bath, 10 Person Occupancy This rare find offers so much space you will forget you are not the only one in the house! The main floor of the home has a large gathering area, dining room, kitchen and all season room. Access the upper deck from the dining or all season room and find a dining table and fire table to enjoy the views by day and by night. Exit the opposite door and you will find a quaint garden and grill for preparing those 'stay at home' meals. The gathering area has a wood burning fireplace and the all season room enjoys a wood stove for additional warmth on those crisp winter days. Also on the main floor you will find a full bath plus two bedrooms, one with a queen bed and a set of full size bunk beds, and the second with a queen and a twin bed. The upper level occupies a master suite with a king bed, grand bathroom with jetted tub, and a large loft outfitted with toys and play furniture. You will also find a computer for your use while you are our guests. The lower level will amaze you! Here you will find the fourth bedroom with a queen bed, two full bath, and a fantastic game/family room with air hockey, slot machines, bar, jukebox, large screen TV, second fireplace, and wait..., a second full kitchen! The sliding door will lead you straight to the covered hot tub, available year round. The fire pit is a perfect spot to end the evening with stories of the days adventures. Guest Access You will have access to the Galena Territory Owners' Club and all it's amenities such as indoor and outdoor pools, game room, fitness center, gym, tennis and basketball courts, and more. The Area Galena IL has hundreds of unique gift and clothing shops, antique stores, art galleries and artist studios. It boasts a rich performing arts community, live music, gourmet delights, as well as a multitude of museums, wineries, historical sites and tours. There are opportunities to enjoy the outdoors golfing, skiing, playing tennis, boating, fishing, zip-lining, hiking, horseback riding, hot-air ballooning and much more. Getting Around A car is necessary to see all that Galena and the surrounding area has to offer! Taxi, Uber and Lyft services are available.

Superhost

Townhouse in Galena

4.87 out of 5 average rating, 169 reviews

Galena Territories 3 level Townhome Sleeps nine

Beautiful vacation home in Galena Territories. Located in central resort core, close to all 4 golf courses, owners club, hiking trails and main lodge. Only 15 minutes drive from historic Galena IL. Three level townhome, large screen TV in living room and family room all bedrooms have HDTV. Upper level BR w/en-suite bathroom. Two BR’s are full sized showers/tubs. All linens/toiletries/coffee/condiments provided. Wood burning fireplace with wood provided. Free access to all owners club facilities.

Guest favorite

Cabin in Savanna

5 out of 5 average rating, 44 reviews

River Rail Retreats Blue Cabin at Palisades

Welcome to River Rail Retreats at Palisades! (formerly The Nest at Palisades) Down a private lane, nestled amidst 5 acres of woods, you'll find 3 Cabins available to rent. The Property & Cabins have undergone New Ownership and extensive remodeling, with brand new furnishings, appliances, & decorations. While located in a country setting, you are still close to Downtown Savanna, Mississippi River, & Palisades State Park. This is a perfect retreat for a blend of tranquility and rustic charm.

Guest favorite

Home in Freeport

4.98 out of 5 average rating, 168 reviews

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

Superhost

Townhouse in Galena

5 out of 5 average rating, 20 reviews

Cozy Sunrise Villa!

1 bedroom, 2 bath townhome with main floor living room, dining room, wall scrabble board, kitchen, full size sofa sleeper, laundry room, gas fireplace. Upper floor has king bedroom with full bath. Back deck off main level. Access to private Walnut Hill pool. Resort amenities include indoor/outdoor pool, game room at Owner's Club, lounge area, tennis, golfing, hiking, walking trails, basketball court, marina for boat rental and fishing, horseback riding. Only 6 miles to downtown Galena.

Guest favorite

Home in Rockford

4.92 out of 5 average rating, 39 reviews

Beautifully home with 5 bedrooms

Experience the ultimate vacation in this newly renovated 5-bedroom and 2-bath rental, perfect for families or groups of friends. Enjoy 4 king & 2 twin beds, a LUX eat-in kitchen, private yard, and a screened porch. This rental also offers on-site laundry and a 2-car garage attached to the property. Plus, pets are allowed so you don't have to leave your furry friends behind! Book your stay today and experience the ultimate getaway at this luxurious and well-appointed short term rental.

Guest favorite

Townhouse in Galena

5 out of 5 average rating, 16 reviews

Perfect Getaway: Newly Renovated

Take it easy at this unique and tranquil getaway. Relax with a few friends at this peaceful place to stay. Located in the Galena Territories, this rental provides something for everyone. During the summer months you can access trails, golfing, an indoor and outdoor pool and so much more. During the winter months you are close to one of the finest ski resorts around. In Fall, access breath-taking views of trees as they change color. All year round there is something to look forward to!

Guest favorite

Home in Galena

5 out of 5 average rating, 8 reviews

New listing for Fall - 4BR FP/Deck/Games/EV

This charming retreat offers a perfect blend of rustic charm and modern comfort. Enjoy stunning forest views, stargazing nights, and the soothing sounds of nature. * 4 bedrooms - up to 10 guests * Newly furnished * Fully equipped kitchen * Wood burning fireplace and stove * Porch swing * Deck w/grill & dining Access to the owner's club featuring swimming, fitness center, tennis and more. Nearby to horseback riding, boat rental, nature trails for hiking, four renowned golf courses.

Superhost

Cabin in Galena

4.88 out of 5 average rating, 126 reviews

Serenity Cabins - A rustic, yet upscale cabin!

Welcome to Serenity Cabins. Whether your stay here is for a vacation, anniversary, family get together, romantic get away, or spiritual retreat, you'll find your stay to be welcoming, relaxing, memorable, full of charm and you'll love the luxurious modern amenities while feeling the rustic atmosphere. You can fall asleep with the sounds of nature and the whispers of the winds. Go for quiet walks as you surround yourself by nature's natural beauty or unwind in front of the fireplace.

Guest favorite

Home in Galena

4.98 out of 5 average rating, 56 reviews

Jackson Ready Properties

Bring the whole family to this great place with lots of room for fun. Enjoy the patio or deck and cozy up to the outdoor firepit. Socialize with family and friends inside with two large living areas featuring plenty of seating and pool, foosball or wet bar to keep guests entertained. Three large bedrooms that sleep 6 comfortably as well as a sofa sleeper for kids or tag-along adults! Located within walking distance to the Owner's Club or a short cruise down the hill to the Marina.

Guest favorite

Home in Galena

4.92 out of 5 average rating, 153 reviews

DunPuttin Place

Nestled on a secluded hillside that overlooks miles of Galena Territory's wildlife preserve, DunPuttin Place offers its guests total privacy, yet the convenience of being only minutes from the area's many popular amenities. DunPuttin Place is not just another carbon copy resort rental. It is a unique private home that has many features seldom found in vacation rentals. It has been tastefully designed and decorated to comfortably accommodate up to 12 guests of all ages.

Guest favorite

Home in McFarland

4.87 out of 5 average rating, 141 reviews

Lovely Waterfront Two Bedroom House

Lovely two bedroom, one bath in a rural residential area of McFarland on inlet that connects to Yahara River and Lake Kegonsa. The home is situated next to a charming campground and marina in nature. Walkable fishing areas. Lake Kegonsa State Park Trail is nearby for walking or snowshoeing. Just a 20 minute drive to downtown Madison! NO PARTIES. You will be asked to leave if there is any party activity seen.