Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite

A living room is displayed with two leather sofas arranged around a centrally located coffee table. A textured area rug covers the hardwood floor. Natural light enters through a large window, illuminating the minimalist decor and decorative elements on the side tables.

Home in Neenah

4.94 out of 5 average rating, 17 reviews

Cozy Boho Home in Neenah

Newly updated home near the heart of Neenah, WI. This home has been meticulously styled with leather sofas, MCM furniture, a high-end Casper King mattress, aesthetic draperies, new appliances, trendy hardwood flooring, ultra comfort bedding, and so much more! Kitchen is fully equipped with basic essentials such as pots, pans, eatery, Keurig coffee maker, full-size fridge, stove, dishwasher, and microwave. You can also enjoy a main-level laundry room with new washer/dryer units detergent supplied

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, 119 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.

Top guest favorite

The entrance of the apartment is highlighted by a sturdy door with decorative window features. A well-maintained pathway leads to the door, flanked by a manicured lawn and flowering plants under the green canopy of surrounding trees.

Guest suite in Fremont

4.98 out of 5 average rating, 91 reviews

Mother in law suite without the mother in law

Private 1 bdrm. apartment with full bath, kitchen, living room, and outdoor private patio. LR has sofa bed. Parking onsite. Owners live in attached house and will be as available as you need, or not if you are looking for privacy. Our home and the attached apt. are located on 3 acres surrounded by trees. We are 20 minutes to Appleton and Oshkosh and about 50 minutes to Green Bay. We are also 7 miles from downtown Fremont and the Wolf River known for it's fishing and boating activities.

Superhost

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 Neenah

4.85 out of 5 average rating, 171 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 cozy firepit area is surrounded by eight Adirondack chairs, set against a backdrop of a vibrant sunset over the lake. The scene is framed by smooth pebbles, while a 60-foot dock extends into the water, creating a serene outdoor atmosphere.

Home in Menasha

4.94 out of 5 average rating, 227 reviews

Newly Updated: LakeViews-Firepit-Kayaks-Boat Dock!

Relax at Sunset Oasis, where stunning lake views and sunsets set the tone for your stay. Sip coffee in the chef’s kitchen, paddle out in kayaks, grill lunch, and dine lakeside. In the evening, cozy up by the fireplace or gather around the firepit under the stars. Stream your favorite shows on the smart TV or explore nearby downtowns just minutes away. This stylish, updated luxury lake house is the perfect escape to unwind, reconnect, and create unforgettable memories.

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, 61 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!

Guest favorite

A charming white cabin is shown with a front porch and stairs leading to the entrance. Lush green grass surrounds the property, along with colorful flower beds. In the background, a red barn is visible, providing a contrast to the cabin's exterior.

Farm stay in Omro

4.88 out of 5 average rating, 85 reviews

Comfy Cabin on 170 Beautiful Acres - Come Explore!

The cabin rests on 180 acres of scenic farm wildlife habitat. The property includes an 1800s-era barn & blacksmith shop, a host of wild & domestic animals, miles of private canal with access to the Wolf & Fox Rivers, a hiking trail, garden, orchard, and much more! The farm has been the pride of our family for 6 generations. A converted grainary, the cabin features a queen bed, full kitchen, full bathroom, high-speed satellite Wifi and smart-TV.

Guest favorite

A welcoming living room features two bright yellow armchairs and a gray sectional sofa. Large windows provide natural light, while a flat-screen TV is positioned on a modern console. A wooden coffee table rests on a plush gray area rug, adding to the cozy ambiance.

Home in Appleton

4.94 out of 5 average rating, 143 reviews

Modern, Freshly Renovated House Near Downtown

✦Nestled in the heart of Appleton, you are close to EVERYTHING when you stay here - very close to Lawrence University, the Performing Arts Center, Mile of Music and more - great location but still VERY quiet area. ✦3 minute drive or 10 minute walk to downtown College Avenue ✦Newly remodeled EVERYTHING, with a fully equipped kitchen for you to cook in ✦Professionally curated decor ✦Green Bay: 35 minutes. Oshkosh: 20 minutes. Mall: 8 minutes.

Guest favorite

A blue cabin is nestled among greenery in a spacious yard, with manicured shrubs lining the gravel driveway. Tall trees surround the property, providing a tranquil atmosphere. A neighboring building is visible, contributing to the serene setting of the retreat.

Home in Winneconne

5 out of 5 average rating, 9 reviews

The little blue jay

Welcome to The Little Blue Jay, a cozy blue cabin nestled in a semi-secluded spot by the lake. This peaceful retreat offers two comfy bedrooms, an open living area and kitchen, and large windows with beautiful lake views. Enjoy a spacious bathroom and a generous yard perfect for relaxing, playing, or evening bonfires. Whether you’re seeking a quiet escape or outdoor adventure, The Little Blue Jay is the perfect place to unwind and recharge.

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

4.86 out of 5 average rating, 223 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, 270 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!