Winchester Vacation Rentals

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Dec 5 - Dec 6
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Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Winchester

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, (348)
"Enjoyed my stay"
United States
Luciana
$77 nightly
The price is $91
Jan 3 - Jan 4, 2026
Total with taxes and fees
Leavenworth Local Hotel
Front of property
Condotels

Condotels

3.0 star property
Lansing
9.0 out of 10, Wonderful, (188)
"Always a pleasant stay Friendly staff, clean rooms and great location "
United States
Leslie
$120 nightly
The price is $140
Jan 4 - Jan 5, 2026
Total with taxes and fees
Condotels
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, (111)
"Thanks for letting us stay. Had a good time"
United States
Janet L.
$280 nightly
The price is $300
Dec 8 - Dec 9
Total with taxes and fees
Cottage On Main- In The Heart Of Weston
Fridge, microwave, oven, stovetop
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.

2.0 star property
Atchison
10.0 out of 10, Exceptional, (13)
"The house was super quiet, clean and conveniently located near the shops and restaurants. The beds were comfortable and our host was incredibly nice. I plan on staying here every time I visit Atchison. "
United States
Veronica
$215 nightly
The price is $242
Dec 8 - Dec 9
Total with taxes and fees
Charming 2-bedroom house in Atchison on quiet brick and tree lined street.
Fridge, microwave, oven, stovetop
7-Bedroom: Hoops, Pickleball, Movies, Books & Games!

7-Bedroom: Hoops, Pickleball, Movies, Books & Games!

Weston
10.0 out of 10, Exceptional, (17)
"We absolutely loved this place!"
United States
Jesse T.
7-Bedroom: Hoops, Pickleball, Movies, Books & Games!
Exterior detail
Newly Remodeled Classic Old Leavenworth Home in the heart of town

Newly Remodeled Classic Old Leavenworth Home in the heart of town

Leavenworth
9.2 out of 10, Wonderful, (27)
"My sister and I stayed 6 days. Check in was easy, and the house was clean and comfortable. The neighborhood felt safe and friendly. We would definitely stay there again."
United States
Valerie V.
$352 nightly
The price is $373
Dec 7 - Dec 8
Total with taxes and fees
Newly Remodeled Classic Old Leavenworth Home in the heart of town
Stovetop
Wild Equine Loft Apartment

Wild Equine Loft Apartment

Weston
10.0 out of 10, Exceptional, (21)
"My friends and I stayed in Weston for the weekend and this place was perfect! "
United States
Lauren M.
$344 nightly
The price is $369
Dec 8 - Dec 9
Total with taxes and fees
Wild Equine Loft Apartment
Living area
NEW Charming 2 bedroom, with cozy, quiet backyard, close to campus and LMH,

NEW Charming 2 bedroom, with cozy, quiet backyard, close to campus and LMH,

2.0 star property
Lawrence
10.0 out of 10, Exceptional, (1)
"Very clean and new decorations, linens, bedding, kitchen items. Very attentive to needs too! :) "
United States
Jill C.
$248 nightly
The price is $263
Dec 10 - Dec 11
Total with taxes and fees
NEW Charming 2 bedroom, with cozy, quiet backyard, close to campus and LMH,
Outdoor dining
Terrific Townhome w/fenced in yard and patio

Terrific Townhome w/fenced in yard and patio

Lawrence
9.8 out of 10, Exceptional, (37)
"Great, the location was perfect and it was a quiet safe area. "
United States
Adrianne F.
$265 nightly
The price is $286
Dec 7 - Dec 8
Total with taxes and fees
Terrific Townhome w/fenced in yard and patio
Property grounds
Quaint house on the bluffs overlooking the scenic Missouri River.

Quaint house on the bluffs overlooking the scenic Missouri River.

Atchison
10.0 out of 10, Exceptional, (44)
"Great location, clean and comfortable stay! Highly recommend if you're going through Atchison. The views and access to the River are great."
United States
Brian B.
Quaint house on the bluffs overlooking the scenic Missouri River.
Terrace/patio
Historical home w gardens in Unique North Lawrence. ACROSS FROM TRAIN DEPOT

Historical home w gardens in Unique North Lawrence. ACROSS FROM TRAIN DEPOT

North Lawrence
9.4 out of 10, Exceptional, (3)
"Great location, loved the garden/outdoor area, and the host was very accommodating. Will definitely look to stay again. "
United States
Nicholas D.
Historical home w gardens in Unique North Lawrence. ACROSS FROM TRAIN DEPOT
Outdoor dining
Charming 1-bedroom apartment in downtown historic Weston

Charming 1-bedroom apartment in downtown historic Weston

Weston
9.4 out of 10, Exceptional, (13)
"Wonderful, quite little basement appt that was clean and all the shops and wineries are in walking distance."
United States
Jeremy
$217 nightly
The price is $217
Dec 7 - Dec 8
Total with taxes and fees
Charming 1-bedroom apartment in downtown historic Weston
Interior
Visit the farm!

Visit the farm!

Dekalb
10.0 out of 10, Exceptional, (45)
"Wonderful property. Very private and cozy. Loved our morning coffee on the back deck overlooking the beautiful green hills and fields. Very clean and had everything we needed. Very nicely decorated- a great experience. "
United States
Susan S.
Visit the farm!
Fridge, microwave, oven, stovetop
Tranquil, upscale house tucked in the woods near Perry Lake, Kansas.

Tranquil, upscale house tucked in the woods near Perry Lake, Kansas.

Ozawkie
10.0 out of 10, Exceptional, (13)
"We enjoyed the house and the location was great. "
United States
Jenell M.
Tranquil, upscale house tucked in the woods near Perry Lake, Kansas.
TV, fireplace
Weston Wanderlust Bed and Breakfast

Weston Wanderlust Bed and Breakfast

Weston
10.0 out of 10, Exceptional, (13)
"Loved it here , clean , cute, comfy beds , safe location "
United States
Brenna L.
Weston Wanderlust Bed and Breakfast
3 bedrooms, WiFi, bed sheets
Wild Feline Retreat

Wild Feline Retreat

Weston
10.0 out of 10, Exceptional, (12)
"We stayed her with some friends for a fun weekend. Great location and great place to stay! "
United States
Spencer H.
$349 nightly
The price is $374
Dec 8 - Dec 9
Total with taxes and fees
Wild Feline Retreat
House (3 Bedrooms) | Interior
Half Mi to Yacht Club: Home by Perry Lake!

Half Mi to Yacht Club: Home by Perry Lake!

3.0 star property
Meriden
10.0 out of 10, Exceptional, (1)
"We came to the area for a tournament and this was our home base for the week—-warm, homey and a great retreat from the gym. We mostly had breakfasts there and then late night snacks. The beautiful country drive to both Topeka and Lawrence was easy. We appreciated the quiet area! "
United States
Gail
Half Mi to Yacht Club: Home by Perry Lake!
Terrace/patio
The Guest House on Seneca with King Bed

The Guest House on Seneca with King Bed

Leavenworth
9.4 out of 10, Exceptional, (9)
"We had a comfortable stay and had everything we needed!"
United States
Linda E.
The Guest House on Seneca with King Bed
Exterior
Fully Renovated Historic Home with bluff views of Missouri River & Valley

Fully Renovated Historic Home with bluff views of Missouri River & Valley

Atchison
10.0 out of 10, Exceptional, (63)
"Property was clean, had everything we needed and more. The views were spectacular, neighbors were friendly. "
United States
Brandy B.
Fully Renovated Historic Home with bluff views of Missouri River & Valley
Fridge, microwave, oven, stovetop
Country Living on 32 Acre Farm

Country Living on 32 Acre Farm

Leavenworth
10.0 out of 10, Exceptional, (3)
"My granddaughter loved the farm animals. Great camping stay. "
United States
DeAnn B.
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

DoubleTree by Hilton Hotel Lawrence

DoubleTree by Hilton Hotel Lawrence

10/10 Excellent
"Everything "
theodoric 1-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Lawrence

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 $91 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.

Explore a world of travel with Expedia

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?

Charming 2-bedroom house in Atchison on quiet brick and tree lined street.: Visitors like this Winchester vacation home rental. It is equipped with a fireplace, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Nell Hill's, or get outside and enjoy nature at Perry Lake. In the larger area, you’ll find Perry Lake Recreation Area and Ozawkie Township Hall.

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.