Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favorite

A lush green lawn extends towards the lake, flanked by two large trees. Two wooden Adirondack chairs provide a comfortable seating area, facing the water. The serene lake view stretches into the distance, with a small boathouse visible nearby.

Home in Oshkosh

4.99 out of 5 average rating, 130 reviews

Cozy Relaxing Lake Home with spectacular sunsets!

Located on the shore of Lake Butte Des Morts Yard,pier(summer months), (sorry we do not allow anything to be tied up to our pier)solo fire pit, grill,seating SUNSETS Lake view Bedroom,Living Room,Dining area Close to Wiouwash trail for hiking, biking,snowmobiling Approx. 40 miles to Lambeau Field Close to EAA Restaurants Shopping Gas fireplace in Living / dining room with a desk Kitchen with space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

Guest favorite

A serene riverside view showcases a grassy area leading to a wooden deck with turquoise chairs. The calm water reflects fluffy clouds above, with buildings in the distance. This peaceful spot offers a perfect setting for relaxation by the river.

Home in Menasha

4.96 out of 5 average rating, 108 reviews

Broad St Riverview Retreat, River Views, Hot tub

Getaway on the river, ultimate comfort, spacious, near Lambeau Field. Five 55” flat screens with Roku! Hot tub, grill, fenced yard. Fully stocked kitchen! Ex-lg island doubles as a game table. Closet full of games for your enjoyment. Walk to breweries, restaurants, coffee shops, supper clubs, trails, Walgreens... 2 fireplaces & the fastest internet available. Sleeps 10. 3 full baths. Plenty of driveway parking. Primary bedroom suite. Large office with double desks, 4 seasons rm with pub table.

Top guest favorite

A modern living area features a striking brick fireplace as a focal point. Natural light floods in through large windows, illuminating the hardwood floor. A comfortable gray couch is positioned beside a black chair, with a TV visible across the room.

Home in Appleton

5 out of 5 average rating, 122 reviews

Appleton Wooded Oasis - Hot Tub-6 Star Hospitality

Relax and enjoy in a beautiful scenic home conveniently located in a quiet wooded neighborhood in Appleton. It has all the elements of being your get away from home. Nearly 3,000 sq. ft. Guests have access to all living areas, modern kitchen, full mason fireplace, vaulted ceilings, large deck and hot tub. Enjoy the backyard with a spacious deck, 7 person hot tub and outdoor fire pit. Five min. from Airport, Downtown, 25 min. to Lambeau and 20 min. to EAA. Includes coffee and breakfast.

Guest favorite

A rustic log cabin is surrounded by greenery, featuring a charming wraparound porch with steps leading up to it. The exterior displays wooden beams and a welcoming front, while a small fence encloses the area, creating a cozy, nature-integrated ambiance.

Farm stay in New London

4.96 out of 5 average rating, 188 reviews

Irish Acres Farm Charm Glamping: FAIRY CABIN

Irish Acres Farm is host to guest friendly activities. Sit & relax or join in farm chores, hike, fish, meditate. Light a camp fire and enjoy Nature at her finest. Experience the coziness of a rustic "tiny house" off-grid log FAIRY CABIN set beside a 1 acre spring fed pond. My place is good for couples, solo adventurers, & families (with kids). No pets or therapy animals allowed. We strive to be a tech free zone (NO WIFI or TV's). A true authentic connection with Nature and each other.

Guest favorite

A log home with a wooden exterior is surrounded by lush greenery. The front porch is adorned with a small blue umbrella and features a set of steps leading to the entrance. Gravel driveway and flower beds enhance the welcoming ambiance of the property.

Home in Oshkosh

4.86 out of 5 average rating, 195 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

A well-lit hallway features smooth wooden flooring and white walls. Two framed botanical prints are displayed on the left. A small table with a plant is positioned near the doorway, which opens into a bathroom. Light filters in from the bathroom window.

Apartment in Downtown Neenah

4.85 out of 5 average rating, 174 reviews

Cozy and Simple Downtown Space

Enjoy this great space in a quiet safe neighborhood. One car allowed at the property! The space has comfortable beds, provided hygiene products, a smart TV and snacks + beverages. Wake up and enjoy coffee provided by us. Shops and restaurants within walking distance! Visit The Plaza downtown with ice skating, fire pits, a coffee shop and more. Great for a couples getaway. Luxury for a great price! A portion of the proceeds from bookings go to housing evacuees, refugees and veterans.

Top guest favorite

A modern living room features a comfortable gray sofa adorned with patterned cushions. A large area rug with a chevron design anchors the space. A wall clock and artwork complement the decor, with a glimpse of the kitchen area visible in the background.

Apartment in Winneconne

4.98 out of 5 average rating, 62 reviews

Boathouse Bungalow

The Boathouse Bungalow is the uniquely perfect getaway located on the river in Winneconne, WI. This bright one bedroom apartment is located on the backside of a large and historical boathouse just a few blocks from the downtown area and features a permanent dock for use. Located in a no-wake zone, the dock is perfect for fishing or tying up a boat overnight. Also close to walking and snowmobile paths, the Boathouse Bungalow is the ultimate retreat for exploring!

Top guest favorite

A relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.

Cottage in Fond du Lac

4.99 out of 5 average rating, 287 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.

Top guest favorite

An open concept living area features a modern kitchen with stainless steel appliances and a marble countertop. A round dining table with upholstered chairs complements the sleek bar stools at the kitchen island. Light wood flooring enhances the spacious feel of the room.

Home in Appleton

4.95 out of 5 average rating, 191 reviews

Modern, Freshly Renovated House - Great Location

-Historic residential district near downtown, Lawrence University, the Performing Arts Center, Mile of Music and more - great location but still VERY quiet area. -30 minutes to Green Bay and Oshkosh -3 season porch -New deck overlooking wooded backyard -Safe, well established neighborhood with tree-lined streets and beautiful parks -Need more space or traveling with friends? Click Visit our profile to see our additional 5★ Appleton properties

Guest favorite

The exterior of a two-story house is shown, featuring a porch and a well-maintained lawn. Large windows are visible, offering natural light to the interior. Surrounding trees provide shade, and a pathway leads to the entrance, enhancing accessibility.

Apartment in Oshkosh

4.85 out of 5 average rating, 226 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.

Top guest favorite

The exterior of a charming barn surrounded by trees features chickens and other birds foraging on the grass. A wooden porch with an American flag is visible, adding to the welcoming ambiance of the property.

Cabin in Winneconne

4.98 out of 5 average rating, 274 reviews

Barndominium with Goats, Hot Tub, Forest & River

The Cloverland Barndominium is a thoughtfully renovated 100-year-old barn sitting on 5+ private acres of forest to explore next to a river. You'll share the land with friendly goats and chickens that you can watch from right outside your window! Outside you'll enjoy walking the trails, feeding the animals, taking the canoe down the river, making a fire in the fire pit, and exploring the forest. Escape the busy world and reset!

Top guest favorite

A cozy sleeping area contains two full-size beds adorned with warm-colored bedding. Nightstands with lamps are placed beside each bed. A comfortable chair sits in the corner, and two windows allow natural light to illuminate the room. Decorative rugs cover the laminate flooring.

Apartment in Oshkosh

4.92 out of 5 average rating, 287 reviews

Rosie's Place A

Hello and Welcome! Rosie's place A features a cozy newly renovated clean furnished upper apartment. Very close to everything in Oshkosh. Great for business travelers, vacationers and visiting University of Oshkosh and Hospital families. Breakfast items, fruit, coffee, tea, soda, water & snacks included. Private parking behind the house. Door code will be provided to enter. No minimum stay!