Vacation rentals in Roscoe

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Top-rated vacation rentals in Roscoe

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

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Guest favorite

A welcoming porch features a classic red grill and comfortable seating. The entrance is adorned with a potted plant, enhancing the home's charm. The light-colored exterior walls are complemented by a vibrant red roof, providing a cheerful atmosphere under a clear blue sky.

Apartment in Monroe

4.92 out of 5 average rating, 13 reviews

McG Resorts Chic Chalet

Enjoy a stylish experience at this centrally-located place. This historic bike/gun shop turned chic chalet-styled cottage is literally steps from a brewery/distillery, stellar restaurants, unique shops & Monroe's historic Square. This cute residence has everything you need whether traveling alone, as a couple, with your friends or family. Professionally designed, this property features all those little extra details to make your stay memorable & shares in the richness of our community's history.

Top guest favorite

A spacious deck overlooks the calm lake, furnished with a dining table under an umbrella and seating for relaxation. A circular hot tub is positioned nearby, surrounded by greenery and offering a serene view of the water.

Home in Freeport

4.98 out of 5 average rating, 176 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.

Top guest favorite

An outdoor fire pit surrounded by wooden benches and chairs is visible in a spacious green area. The cabin in the background features a red exterior and large windows framed by trees, offering a serene spot for gathering.

Home in Elkhorn

4.98 out of 5 average rating, 146 reviews

Red Lodge - Game Room, Hot Tub, Near Lake

Looking for a memorable Wisconsin vacation experience? The Red Lodge is the ideal blend of comfort and style. Super clean, fully stocked, with gorgeous outdoor green spaces and unique amenities, you'll love it here! Jeff - "The devil is in the details, and no detail is overlooked here." Kelsey - "We are obsessed! This is THE nicest Airbnb we've stayed in across the country.. There was something truly unique about each room." Alia - "Hands down the best Airbnb we have ever stayed in."

Guest favorite

A screened porch is shown, furnished with a comfortable seating area featuring four wicker chairs and a matching table. Natural light filters through the surrounding windows, enhancing the airy feel, while a door leads to the outside space.

Home in Rockford

4.93 out of 5 average rating, 45 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.

Top guest favorite

The Spanish-style villa is framed by lush greenery and a landscaped garden featuring stone pathways. Distinctive red windows and subtle lighting enhance the exterior's charm. The upper level is visible, showcasing a unique architectural design that complements the overall aesthetic.

Home in Rockford

4.98 out of 5 average rating, 289 reviews

Hidden Gem Spanish Style Villa

Ask about our special, Mon-Thurs, book 2 nights, get a 3rd free! Unique to Northern Illinois, this Spanish style Villa sleeps 10+ , boasts five patios, a Cantina, 7 ARCADES, HOT TUB, and many surprises you will find as you look at every turn to something unexpected. This property is filled with beautiful furnishings, featuring a balcony off of the upper level that boasts a 12 foot ceiling. Everything from two walk in showers, a jet tub and a hot tub for any level of self-care desired.

Guest favorite

Home in Delavan

4.89 out of 5 average rating, 113 reviews

Victorian in Delavan, near Lake Geneva & Alpine

Family & friends will be close to all Delavan offers staying at this beautiful historical 1901 Victorian home. One block from charming brick-paved downtown Delavan, you'll have shopping, music, parks & great restaurants at your fingertips! Your private gazebo w/ fireplace provides an ideal retreat, while the bandstand livens things up across the street! Playgrounds, sledding hill, beach, lake & arboretums are all within 4 blocks; skiing & Lake Geneva are just a 15-minute drive away!

Guest favorite

A private pier extends into the water, adorned with white seating and a patterned rug. A lakefront cottage with large windows is visible in the background, surrounded by greenery, while trees and a blue sky reflect a serene environment.

Cottage in Delavan

4.93 out of 5 average rating, 84 reviews

Spring Special Lakefront Cottage on Delavan Lake

Escape to this lakefront cottage for your next “lake-cation”. The newly renovated Cottage on Willow Point would be the perfect destination. 3 bedroom, 1.5 bath and sleeps up to 9 comfortably. Beautiful outdoor deck and dining space. 15 steps from the lake and includes a private 120 foot pier, sun deck and ladder! We are a fully furnished rental. We also rent another cottage that can accommodate bigger groups. Please email for more info! Thecottageondelavanlake@gmail.com

Top guest favorite

A fire pit is situated on a grassy area, surrounded by a stone border. A metal log holder filled with stacked wood sits nearby. Tall trees provide a backdrop, and gentle shadows are cast across the lawn.

Home in Elkhorn

4.98 out of 5 average rating, 123 reviews

Cozy Country Cottage near Lake Geneva, WI

Our Cozy Cottage features 3 comfortable bedrooms and nightly magnificent sunsets. Nestled on a country road, the house offers plenty of space to rest after visiting Lake Geneva, Lauderdale lakes, biking at Kettle Moraine or site seeing in the area. It’s close to Walworth County fair grounds where the flea market, Das Fest and Rib Fest are held. This is country living with plenty of opportunity to enjoy the beautiful outdoors or the peace and quiet of the countryside.

Guest favorite

A spacious living area features rustic wooden beams and a stone fireplace as its centerpiece. Cozy leather seating surrounds a low coffee table, ideal for gatherings. Large windows provide views of the surrounding greenery, while a dining table and chessboard add functionality to the space.

Home in Cherry Valley

4.9 out of 5 average rating, 40 reviews

Cozy Log Cabin: River Views+Sauna+Fire pit+hot tub

Welcome to your perfect getaway! Our house is ideal for couples, families, or small groups looking to escape the hustle and bustle of daily life and reconnect with nature. ★ Relax in Hot Tub ★ Rest in Sauna ★ Sleep - 3 Bedrooms, 5 beds ★ Gather around fire pit with family and friends ★ Rest peacefully in a 3 king-size beds ★ Watch your favorite shows on 4 Roku TV’s around house ★ Stay connected with fast Wi-Fi. ★ Play foosball tournaments ★ Hiking, fishing, kayaking.

Superhost

The spacious kitchen features wooden cabinetry and modern stainless steel appliances. An island with seating for four is highlighted by warm lighting. The open layout is complemented by rustic wood paneling and large windows, allowing natural light to fill the area.

Barn in Davis

5 out of 5 average rating, 4 reviews

Sunrise Country Views

You won’t forget the peaceful surroundings of this rustic destination. Rejuvenate yourself when you stay in our rustic 1930's barn. Come out to the country to enjoy the outdoors. Take time to connect with nature while taking in a sunrise or a sunset on the waterfall patio. Stroll the flower beds or take a short travel to small towns for biking, shopping, winery/brewery, canoeing, and entertainment.

Top guest favorite

A wooden deck overlooks the Sugar River, featuring a circular table and four chairs. Sunlight filters through the trees, casting a warm glow on the water. In the background, the flowing river is visible, with a dam adding to the natural scenery.

Apartment in Albany

4.94 out of 5 average rating, 182 reviews

Sugar River Hideaway

Newly renovated, 3-bedroom vacation home located on the Sugar River in downtown Albany. Albany is a quaint little town with a lot to offer. Enjoy tubing/canoeing down the river, a diner, pizza place, Italian restaurant, 3 taverns, and a bowling alley all within the downtown block. With being only 30 miles away from Madison and 17 miles from New Glarus, Albany is a prime location for your stay!

Top guest favorite

The exterior of the red cottage is surrounded by lush green grass and trees. A spacious front porch features large glass doors leading into the home, while a fenced yard includes several outdoor chairs. The area offers a peaceful, natural setting.

Tiny home in Delavan

4.98 out of 5 average rating, 54 reviews

Tiny Red House on Lake Delavan

You’ll treasure your time at this memorable place. Perfect for single family or couple with dog for weekend or week long summer get away. Within 15 min to all the the lake geneva/lake delavan area has to offer including Friday-Night Fish Fry, shopping, championship golf courses, boat rental, lakeside dining, downtown Lake Geneva/Delavan/Fontana, coffee shops, antiques, and fine dining .