Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite

Rental unit in Appleton

4.97 out of 5 average rating, 143 reviews

Homey lower level apartment with private entrance

This living space is in the lower level of our ranch home, which is located in a lovely and quiet neighborhood. The furnishings in this area are mostly antique pieces that came from special family members. You may also use the screen porch and patio for relaxing. You will have a private entrance through the garage so you can come and go as you like. The kitchen is furnished so you may cook; there is no dishwasher. We will furnish paper products. There are also many restaurants close by.

Guest favorite

Home in Appleton

4.9 out of 5 average rating, 109 reviews

Apple Core Cottage

Apple Core Cottage is centrally located in Appleton. The neighborhood is welcoming. The cottage has a private backyard and deck. Fifteen minutes from the Appleton airport, 25 minutes to Lambeau field and 20 minutes to EAA. PLEASE NOTE: We have stays in 3 north eastern Wisconsin locations: Apple Core Cottage in Appleton airbnb.com/h/applecorecottage Heart of the Door Homestead in Door County, Peninsula Center airbnb.com/h/heartofthedoor Up Top Downtown in Green Bay airbnb.com/h/uptopdowntown

Superhost

Guest suite in Winneconne

4.8 out of 5 average rating, 218 reviews

Lake Winneconne Area Cottage

Northwoods-ish rustic cabin: 750 sq.ft., open-concept, lotsa windows, repurposed oak floor, 3/4 bth, equipped kitchen, dining/fun bar, two decks, E &W. 1 Qn, 1 dbl bed, qn. hide-a-bed, 1 twin. Optional: qn or twin air-bed. Desk, dresser, views , cable TV, wifi, stereo, heat/AC. Access to Lake Winneconne public boat ramp, 200 yrds! On-site & off-st. parking trailers. Quiet neighborhood; 3 mi. from Winneconne; easy access to Oshkosh, Green Bay, Fox Cities. Fun, not fussy seasonal decor.

Guest favorite

Home in Oshkosh

4.99 out of 5 average rating, 114 reviews

Beautiful Warm and Cozy Lake Home Sunsets and more

Cozy home located in a small neighborhood on the east shore of Lake Butte Des Morts. One bedroom with sleep number queen bed with lake view.Living room / dining/ desk area with gas fire place overlooking the lake. Kitchen with plenty of space for cooking. Washer/dryer off of kitchen. Spectacular sunsets, fishing(seasonal), solo fire pit provided with outdoor seating! Short walk to Wiouwash Trail for biking, walking and snowmobiling. Close to EAA Grounds, Restaurants,etc! Off street parking

Guest favorite

Loft in Amherst

4.96 out of 5 average rating, 112 reviews

Tiny Town Bakery Flatlet

Ever wanted to see what goes on in a commercial bakery? Imagine waking to the aroma of baking bread and cinnamon rolls? Get a bird's eye view into the kitchen of the Village Hive Bakery Kitchen while staying in the newly renovated "flatlet". Salvaged & repurposed building supplies used to create a unique studio apartment above the bakery retail. Guests can enjoy the retail farmhouse table and comfortable seating space by the Main Street picture window. Cooking/baking classes available.

Guest favorite

Cabin in Wild Rose

4.9 out of 5 average rating, 547 reviews

Postcard Cabins Wild Rose - Milwaukee

An easy drive from the city, Postcard Cabins, formerly Getaway, is the ultimate way to experience the great outdoors. Nestled across acres of private woodlands, our tiny cabins have everything you need (AC/Heat, en-suite bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you disconnect from the everyday. As part of your stay, you'll receive a complimentary allocation of provisions, like s’mores, coffee and more.*

Guest favorite

Home in Oshkosh

4.88 out of 5 average rating, 174 reviews

Go and Go

Cozy 2 bedroom Log home. Can sleep 4-6. Across the street from Lake Winnebago. Short walk to park, zoo and boat landing. 6.5 miles to EAA grounds. Off street parking. Close to shopping, restaurants and downtown Oshkosh. Great rental for Air Show, Book now and bring your boat, jet ski, trailer, and fishing gear or just go sightseeing, dining and relaxing. Full kitchen, New Bath. Very comfortable with a great location. Perfect place to stay for family with students at UWO. Book now!

Guest favorite

Cabin in Fox Lake

4.96 out of 5 average rating, 164 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing, swimming and boating and in the winter have fun ice fishing by walking to the lake out your back door! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum, including children. *All dogs/pets must be pre-approved by the host. There is a $50 pet fee/stay.

Guest favorite

Guest suite in Waupaca

4.95 out of 5 average rating, 207 reviews

Adventure Outpost for 8 near Chain O Lakes

We’re located just outside of town with easy access to all that the beautiful Waupaca area has to offer. Only 10 minutes from the Chain! The property is surrounded by Maple and Oak mature forest yet has an open meadow perfect for picnics and star gazing. It is beautiful here; you can rest and recharge close to nature. Adventure Outpost is totally updated and designed for your comfort and convenience. The space is cozy, light and refreshing and big enough for the whole family!

Guest favorite

Cottage in Fond du Lac

4.98 out of 5 average rating, 249 reviews

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Guest favorite

Rental unit in Oshkosh

4.85 out of 5 average rating, 185 reviews

No Cleaning Fees! 2 Bedroom Apartment By The Lake

We’re transparent with our pricing, that’s why we don’t have cleaning fees! The price you see is the price you pay (local taxes still apply). Come stay near the heart of Oshkosh - you’ll be on the second floor with views of Lake Winnebago. If you need anything during your stay we live on-site and are only a message away. Don’t worry though, the units are completely separated so you’ll have all the privacy you desire during your stay.

Guest favorite

Cabin in Hancock

4.98 out of 5 average rating, 200 reviews

Peaceful Cabin in the Woods

Our cabin has all the amenities a family could need, but is the perfect getaway from city life. Located on 5 secluded acres in Hancock, Wisconsin. Minutes from downtown Wautoma. Surrounded by woods on all sides, with plenty of open area for outdoor activities. A peaceful setting to enjoy a cup of coffee or a glass of wine while listening to the birds from the porch swing, or around the crackling fire at night, toasting marshmallows.