Winchester Holiday Rentals

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Holiday Rentals in Winchester

Leavenworth Local Hotel

2.5 star property
8.8 out of 10, Excellent, (289)
"Really nice hotel"
The price is AU$181
includes taxes & fees
18 Feb - 19 Feb
Leavenworth Local Hotel

Beautiful estate in the bluffs with breath taking views and a private air strip!

9.2 out of 10, Wonderful, (24)
"We had two groups of families stay for the Thanksgiving Holiday. A total of 13 adults and 6 grandchildren 6 and under. It was a fabulous stay. This VRBO was beautifully decorated for the Holiday a very nice touch and surprise. I would definitely recommend this place to others. "
The price is AU$2,729
includes taxes & fees
18 Feb - 19 Feb
Beautiful estate in the bluffs with breath taking views and a private air strip!

Condotels

3.0 star property
9.0 out of 10, Wonderful, (178)
"Check in was very easy and the people working were very friendly. The facilities were nice and comfortable. I would definitely recommend."
The price is AU$200
includes taxes & fees
18 Feb - 19 Feb
Condotels

Cottage On Main- In The Heart Of Weston

8.8 out of 10, Excellent, (89)
"It was roomy, clean and a great location!"
The price is AU$477
includes taxes & fees
18 Feb - 19 Feb
Cottage On Main- In The Heart Of Weston

Flight Of Adventure

10.0 out of 10, Exceptional, (34)
"Great place for family and friends to gather while visiting Benedictine College. The backyard patio and fire ring are amazing. The house is clean and comfortable with responsive hosts."
Flight Of Adventure

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

10.0 out of 10, Exceptional, (7)
"Outstanding all the way around. Owner very responsive to all our questions"
7-Bedroom: Hoops, Pickleball, Movies, Books & Games!

Charming 1-bedroom apartment in downtown historic Weston

10.0 out of 10, Exceptional, (1)
"Great location and clean! Very close to the main street so walking after arriving in Weston was made easy. "
The price is AU$192
includes taxes & fees
18 Feb - 19 Feb
Charming 1-bedroom apartment in downtown historic Weston

Atchison 1870 Farmhouse

Atchison 1870 Farmhouse

"The Oz experience at Kelly's House". There's no place like home!

10.0 out of 10, Exceptional, (16)
"We were in town for BC Scholars weekend for my daughter. The house was full of Oz memorabilia and lots of fun to look at! We were very comfortable and had all the essentials. The host was very friendly and took care of any issues very quickly. We hope to stay again in the near future!"
"The Oz experience at Kelly's House". There's no place like home!

Wild Feline Retreat

10.0 out of 10, Exceptional, (5)
"Outstanding place to stay!"
The price is AU$667
includes taxes & fees
18 Feb - 19 Feb
Wild Feline Retreat

Marr Manor - Studio B&B downtown

9.8 out of 10, Exceptional, (42)
"Place was very clean when we got there, check in was as easy as it gets, quiet, easily walkable to downtown, great value for the money. Would definitely stay here again. "
The price is AU$392
includes taxes & fees
18 Feb - 19 Feb
Marr Manor - Studio B&B downtown

Visit the farm!

10.0 out of 10, Exceptional, (39)
"This was a great place for a weekend away with friends with plenty of room to spread out. The house was well stocked with everything we needed. The house was well decorated making it feel like home. We enjoyed our stay! "
Visit the farm!

Terrific Townhome w/fenced in yard and patio

9.8 out of 10, Exceptional, (20)
"We stayed the week of Christmas. Great location in a quiet neighborhood with plenty of room to relax and get a good night's sleep. Would stay here again if we will be in the area."
The price is AU$483
includes taxes & fees
18 Feb - 19 Feb
Terrific Townhome w/fenced in yard and patio

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

10.0 out of 10, Exceptional, (48)
"Such a wonderful house. So cozy, comfy quiet and charming. Clean and had everything we needed. Loved looking out over the river every morning. The trip to the museum next door was a highlight. We WILL be back when we visit family. "
Fully Renovated Historic Home with bluff views of Missouri River & Valley

The Guest House on Seneca with King Bed

10.0 out of 10, Exceptional, (2)
"Stayed twice-Nice place & great host!!"
The price is AU$412
includes taxes & fees
16 Mar - 17 Mar
The Guest House on Seneca with King Bed

Modern Strawbale on 10 Private Acres

9.4 out of 10, Exceptional, (13)
"We had a great time at the strawbale. Plenty of space, beds, and bathrooms for our party of 7."
Modern Strawbale on 10 Private Acres

The Landing is a Cheerful 3 bedroom 2 bath home!

10.0 out of 10, Exceptional, (24)
"Perfect for what we needed"
The Landing is a Cheerful 3 bedroom 2 bath home!

Bee & Bee Bungalow - Studio B&B downtown

10.0 out of 10, Exceptional, (15)
"Location is great, right near downtown. Host was wonderful, great communication. Loved the property. Very comfortable. Would definitely stay again."
The price is AU$367
includes taxes & fees
18 Feb - 19 Feb
Bee & Bee Bungalow - Studio B&B downtown

Quaint house on the bluffs overlooking the scenic Missouri River.

10.0 out of 10, Exceptional, (22)
"The property was clean and cozy. We all enjoyed our stay."
Quaint house on the bluffs overlooking the scenic Missouri River.

Calming Cabin near Perry Lake

9.0 out of 10, Wonderful, (9)
"Our second visit and we will return! "
Calming Cabin near Perry Lake
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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Other types of properties in Winchester you may be interested in

Comfort Inn & Suites Lawrence - University Area

2.5 star property
8.6 out of 10, Excellent, (926)
"Friendly and helpful staff."
The price is AU$160
includes taxes & fees
23 Feb - 24 Feb
Comfort Inn & Suites Lawrence - University Area

DoubleTree by Hilton Hotel Lawrence

4.0 star property
8.4 out of 10, Very good, (1000)
"It was nice!"
The price is AU$153
includes taxes & fees
23 Feb - 24 Feb
DoubleTree by Hilton Hotel Lawrence

Leavenworth Local Hotel

2.5 star property
8.8 out of 10, Excellent, (289)
"Really nice hotel"
The price is AU$181
includes taxes & fees
18 Feb - 19 Feb
Leavenworth Local Hotel
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.

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

Beautiful estate in the bluffs with breath taking views and a private air strip!: This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

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 wider area, you’ll find Delaware State Park and International Forest of Friendship.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip.