Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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

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Top guest favourite
A serene view of the water at dusk is framed by trees along the riverbank. The calm surface reflects soft colors of the sunset, enhancing the tranquil natural setting.
Home in Appleton
4.97 out of 5 average rating, 119 reviews

Riverfront log cabin in the heart of the valley

◖30 minutes to Oshkosh(EAA) & Green Bay(Lambeau), 10 minutes to Downtown Appleton ◖10 minutes to Kimberly boat launch; travel the Fox River Locks system You will LOVE this property: ◖Outstanding views from the amazing sunsets to the relaxing water & wildlife ◖Newly renovated with many amenities ◖Enjoy the Northwoods setting in the heart of the valley ◖Relax at end of the day sitting around a campfire or by indoor fireplace ◖Tie your boat to dock in front of property ◖Full kitchen/outdoor grill

Superhost
A modern kitchen features a large island with seating for five. Light-colored cabinetry complements granite countertops. Stainless steel appliances, including a gas stove and hood, are visible. In the background, a dining table and a comfortable living area can be seen, enhancing the open layout.
Home in Fremont
4.85 out of 5 average rating, 80 reviews

5bed/3ba Steps to the boat launch & Fremont Beach!

Welcome to our 5-bed/3-ba Airbnb, directly across the Wolf River in the picturesque town of Fremont, Wisconsin. Walk over to the Nauti Turtle for dinner and drinks on the river or head down to the Fremont Beach for swimming and launching your boat. The house has a 4 bedroom, 2 bath in the main area and an attached private 1b/1bath suite! The screened in porch is ideal to spend mornings & evenings. Children's items, the fire pit (w/wood), kitchen and grill are all prepared for your easy arrival!

Top guest favourite
Home in Omro
5 out of 5 average rating, 16 reviews

Fox River Fishing & Relaxation

Newly remodeled home on the Fox River. Perfect for a fishing trip, family getaway or time with your friends! This property comes with all the amenities you will need from a fish cleaning station to high speed WIFI, Spectrum TV & beds that were picked out with the utmost comfort in mind! Bring your boat and tie up to the seawall so you can jump in to fish on the Fox River and various lakes. The outdoor space is ideal for relaxation, meals, games and time by the firepit. Enjoy beautiful sunsets!

Top guest favourite
Home in Appleton
5 out of 5 average rating, 167 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, wood fireplace, vaulted ceilings, spacious sunroom, large deck and therapeutic hot tub. Enjoy the scenic backyard with a large deck, 7 person hot tub and fire pit. Five minutes from airport, vibrant downtown, 25 min. to Lambeau. Includes breakfast.

Top guest favourite
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, 191 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 favourite
Cottage in Princeton
4.96 out of 5 average rating, 235 reviews

RiverFront Cottage>Private Pier>Firepit & Wildlife

Cute little cottage located right on the Fox River overlooking the peacefulness nature has to offer. Enjoy your very own private dock as well as 200 feet of river frontage surrounded by tall mature trees. Be submerged by the community of fishermen (& women) located on Puckaway Lake, surround yourself with wildlife, or paddle down the Fox River. Soak up the sun on the dock or learn how to build the best fire in the fire pit! The adventure is all around you! Which one will you be choosing?

Top guest favourite
A charming cottage exterior is presented with blue siding and white trim. Windows are adorned with flower beds featuring vibrant greenery. A small porch entry is visible, with a path leading up to it. The surrounding area showcases well-maintained grass and garden elements.
Home in Appleton
4.95 out of 5 average rating, 43 reviews

The Cozy Cottage

This special place is close to everything, making it easy to plan your visit. If it's for a weekend getaway, or for the business professional that's needing a long term stay, this is a perfect fit for all. This property is unique for there is only a few like it in Appleton. It's located behind the main house which I reside, but don't let it fool you. It is a quite, private place, with lots of character. When walking in, you get that cozy cottage feel that will make you feel right at home.

Top guest favourite
The exterior of a cabin is depicted, featuring large windows framed by wood. Warm light emanates from within, revealing a cozy interior with a lamp and seating. Snow covers the ground, and icicles hang from the roof, creating a serene winter scene.
Cabin in New London
4.99 out of 5 average rating, 128 reviews

Secluded Cabin with Sauna

Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

Top guest favourite
Cabin in Cascade
5 out of 5 average rating, 261 reviews

sauna and hot tub on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Top guest favourite
The cottage features a long, metal-roofed exterior with gray siding and contrasting purple shutters. Lush greenery surrounds the home, including decorative flower beds. A paved pathway leads to the entrance, highlighting the spacious yard. Sunlight enhances the bright and welcoming appearance.
Guest house in Oshkosh
4.95 out of 5 average rating, 196 reviews

Cottage on Lake Winnebago

Furnished Cottage on Lake Winnebago with beautiful sunrises. 1 bedroom with queen bed. There is plenty of space for air mattresses in common areas. 1 queen air mattress available. One bath, full kitchen fully stocked with dining area, bring your own food to prepare. Bring your water toys or boat, launch nearby and dock access in warmer months with great fishing. Winter months, bring your snowmobile, trails nearby. Great ice fishing when lake is frozen and ice is safe.

Top guest favourite
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.
Flat in Winneconne
4.99 out of 5 average rating, 69 reviews

Boathouse Bungalow

Enjoy a unique getaway in our historic “Boathouse Bungalow” on the Wolf River. The location could not be more perfect when visiting the scenic Fox River Valley; close to walking paths, snowmobile trails and within walking distance to downtown Winneconne. The permanent dock is in a no-wake zone, great for fishing, tying up boats or just relaxing. Located 12 miles to Oshkosh, 23 to Appleton and 48 to Lambeau. A wonderful retreat for making lasting memories.

Guest favourite
Home in Appleton
4.89 out of 5 average rating, 183 reviews

Classic Character Home, Near Downtown & Lawrence

✦A few blocks from Lawrence University campus, the Performing Arts Center, Mile of Music and more - great location but still VERY quiet area ✦Pleasant 10 minute walk to downtown ✦Dogs allowed with pre-approval & pet fee ✦Fully equipped remodeled kitchen for you to cook in ✦Tons of character in this charming home ✦1 full bathroom ✦Green Bay: 35 minutes. Oshkosh: 20 minutes. Mall: 8 minutes (Garage available upon request)

Popular amenities for Winchester holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Winnebago County
  5. Winchester