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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winchester vacation rentals

Room, 1 King Bed, Non Smoking | Premium bedding, down comforters, desk, laptop workspace

Leavenworth Local Hotel

Leavenworth Local Hotel
2.5 star property
Leavenworth
8.8 out of 10, Excellent, (412 reviews)
"Wonderfully unique experience. Helpful folks. Perfect."
United States
Loyanne
$81 nightly
The price is $95
Jul 26 - Jul 27
Total with taxes and fees
Leavenworth Local Hotel
Exterior

Weston Home perfectly located. Walk from the house and explore town!

Weston Home perfectly located. Walk from the house and explore town!
Weston
9.0 out of 10, Wonderful, (21 reviews)
"The house was amazing and we are in love with the cats!"
United States
Devin H.
$291 nightly
The price is $311
Jul 12 - Jul 13
Total with taxes and fees
Weston Home perfectly located. Walk from the house and explore town!
Fridge, microwave, oven, stovetop

Cottage On Main- In The Heart Of Weston

Cottage On Main- In The Heart Of Weston
Weston
8.8 out of 10, Excellent, (128 reviews)
"The breakfast item were nice!"
United States
Leanne L.
$278 nightly
The price is $297
Jul 12 - Jul 13
Total with taxes and fees
Cottage On Main- In The Heart Of Weston
TV

Wild Feline Retreat

Wild Feline Retreat
Weston
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place in a perfect location!"
United States
Alison E.
$439 nightly
The price is $469
Jul 13 - Jul 14
Total with taxes and fees
Wild Feline Retreat
Interior

Charming 2-bedroom house in Atchison on quiet brick and tree lined street.

Charming 2-bedroom house in Atchison on quiet brick and tree lined street.
Atchison
10.0 out of 10, Exceptional, (21 reviews)
"Great place in a nice neighborhood. The host is very friendly and helpful!"
United States
Nathan D.
$199 nightly
The price is $223
Jul 20 - Jul 21
Total with taxes and fees
Charming 2-bedroom house in Atchison on quiet brick and tree lined street.
Interior

Cozy Cabin Rental on Sacred Land Ideal for Glamping in Kansas

Cozy Cabin Rental on Sacred Land Ideal for Glamping in Kansas
Tonganoxie
10.0 out of 10, Exceptional, (3 reviews)
"There is a well-kept hiking train on the property and lots of cute places to enjoy the outdoors. The cabin itself was very cute. "
United States
Rebecca S.
$192 nightly
The price is $207
Jul 16 - Jul 17
Total with taxes and fees
Cozy Cabin Rental on Sacred Land Ideal for Glamping in Kansas
Interior

Newly Remodeled Classic Old Leavenworth Home in the heart of town

Newly Remodeled Classic Old Leavenworth Home in the heart of town
Leavenworth
9.4 out of 10, Exceptional, (34 reviews)
"Beautiful home with easy access! We loved using the large kitchen and living space. Would recommend some hand towels and smoke detectors, but everything was great!"
United States
Dace
$318 nightly
The price is $336
Aug 9 - Aug 10
Total with taxes and fees
Newly Remodeled Classic Old Leavenworth Home in the heart of town
Exterior

Beautiful Historic 2-bedroom house with AC in charming Atchison, near college

Beautiful Historic 2-bedroom house with AC in charming Atchison, near college
Atchison
10.0 out of 10, Exceptional, (1 review)
"The house was perfect for our family of four for a long holiday weekend! All of the rooms were extremely comfortable and equipped with everything we needed. The location was great to be able to walk downtown and the riverwalk! Susan was very easy to communicate with. This is a great rental in Atchison! Would highly recommend and will be renting again!"
United States
Lauren E.
$154 nightly
The price is $176
Jul 13 - Jul 14
Total with taxes and fees
Beautiful Historic 2-bedroom house with AC in charming Atchison, near college
Stovetop

Wild Equine Loft Apartment

Wild Equine Loft Apartment
Weston
10.0 out of 10, Exceptional, (32 reviews)
"Great Place"
United States
Joe H.
$439 nightly
The price is $469
Jul 13 - Jul 14
Total with taxes and fees
Wild Equine Loft Apartment
Interior

Pet-Friendly 3BR Near Kansas City, Fenced Yard, King Suite

Pet-Friendly 3BR Near Kansas City, Fenced Yard, King Suite
Tonganoxie
10.0 out of 10, Exceptional, (3 reviews)
$411 nightly
The price is $439
Jul 13 - Jul 14
Total with taxes and fees
Pet-Friendly 3BR Near Kansas City, Fenced Yard, King Suite
Outdoor dining

Charming 1-bedroom apartment in downtown historic Weston

Charming 1-bedroom apartment in downtown historic Weston
Weston
9.0 out of 10, Wonderful, (20 reviews)
"Great location. Easy check in!"
United States
Jennifer H.
$200 nightly
The price is $213
Jul 13 - Jul 14
Total with taxes and fees
Charming 1-bedroom apartment in downtown historic Weston
Fridge, microwave, oven, stovetop

Terrific Townhome w/fenced in yard and patio

Terrific Townhome w/fenced in yard and patio
Lawrence
10.0 out of 10, Exceptional, (47 reviews)
"This place is well maintained, super clean, and had everything we needed!"
United States
Morgan J.
$280 nightly
The price is $306
Aug 2 - Aug 3
Total with taxes and fees
Terrific Townhome w/fenced in yard and patio
Property grounds

Spacious 7-bedroom house with WiFi and game room in charming Meriden.

Spacious 7-bedroom house with WiFi and game room in charming Meriden.
Meriden
10.0 out of 10, Exceptional, (8 reviews)
"We loved it!"
United States
Jeri B.
$800 nightly
The price is $838
Jul 13 - Jul 14
Total with taxes and fees
Spacious 7-bedroom house with WiFi and game room in charming Meriden.
Fridge, microwave, oven, stovetop

Secluded Cabin near Lake Perry

Secluded Cabin near Lake Perry
Oskaloosa
9.4 out of 10, Exceptional, (6 reviews)
"Very clean! Very comfortable. Host answered all questions quickly. Great place to stay. "
United States
Rodney A.
$285 nightly
The price is $294
Aug 2 - Aug 3
Total with taxes and fees
Secluded Cabin near Lake Perry
Smart TV

Farmhouse on the Prairie - You can see for miles!

Farmhouse on the Prairie - You can see for miles!
valley falls
10.0 out of 10, Exceptional, (19 reviews)
"This stay was super amazing. It was very cute, clean, quiet, no real close neighbors. The perfect little getaway for our anniversary, that we definitely needed... "
United States
Courtney S.
$210 nightly
The price is $217
Jul 20 - Jul 21
Total with taxes and fees
Farmhouse on the Prairie - You can see for miles!
Interior

Clean, easily accessible 2bdrm apartment with AC. 2 mins to base - 15mins to KC

Clean, easily accessible 2bdrm apartment with AC. 2 mins to base - 15mins to KC
Leavenworth
$241 nightly
The price is $255
Aug 3 - Aug 4
Total with taxes and fees
Clean, easily accessible 2bdrm apartment with AC. 2 mins to base - 15mins to KC
Smart TV, fireplace, stereo

Country Living on 32 Acre Farm

Country Living on 32 Acre Farm
Leavenworth
10.0 out of 10, Exceptional, (3 reviews)
"My granddaughter loved the farm animals. Great camping stay. "
United States
DeAnn B.
$133 nightly
The price is $140
Aug 3 - Aug 4
Total with taxes and fees
Country Living on 32 Acre Farm
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Comfort Inn & Suites Lawrence - University Area

Comfort Inn & Suites Lawrence - University Area

10/10 Excellent
"Front desk staff was super helpful."
Ruth 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Lawrence - University Area

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we have vacation rentals close to the most popular attractions in Winchester, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Winchester has to offer?

Cottage On Main- In The Heart Of Weston: You might want to consider this vacation home rental near Winchester, which is located near skiing and has a garden, a selection of games, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like The Sallie House, or get outside and enjoy nature at Perry Lake. In the larger area, you’ll find Perry Lake Recreation Area and Atchison County Historical Society Museum.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Winchester. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family getaway.