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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester holiday rentals

A modern hotel room with a kitchenette, a bed, a desk, and a bathroom.

1. Leavenworth Local Hotel

Leavenworth Local Hotel
2.5 star property
Leavenworth
8.8 out of 10, Excellent, (447 reviews)
"Grat place in downtown Leavenworth. Close to everything in the area. Hotel is clean and staff saw to all of needs. Highly recommended!"
United States
James
The price is HK$636
HK$748 total
includes taxes & fees
15 Oct - 16 Oct
Leavenworth Local Hotel
A modern kitchen with stainless steel appliances, wooden cabinets, and a black countertop.

2. Secluded Cabin near Lake Perry

Secluded Cabin near Lake Perry
Oskaloosa
9.4 out of 10, Exceptional, (6 reviews)
"The host was very pleasant and easy to work with. We are so appreciative for them sharing their home with us. It was great."
United States
Jennifer G.
The price is HK$950
HK$2,269 total
includes taxes & fees
26 Oct - 27 Oct
Secluded Cabin near Lake Perry
A cozy RV interior with a leather sofa, a coffee maker, and a window offering a view of the outside.

3. 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.
The price is HK$683
HK$1,087 total
includes taxes & fees
15 Oct - 16 Oct
Country Living on 32 Acre Farm
Interior

4. 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)
"This place was absolutely perfect! So many thoughtful touches to make this a memorable stay!"
United States
Cristi K.
The price is HK$1,396
HK$1,702 total
includes taxes & fees
15 Oct - 16 Oct
Cozy Cabin Rental on Sacred Land Ideal for Glamping in Kansas
A hallway with wooden flooring, a white door, and a ceiling light.

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

Charming 2-bedroom house on quiet brick and tree lined street.
Atchison
10.0 out of 10, Exceptional, (25 reviews)
"Great location near campus and downtown. Beautifully remodeled inside. Host was great with communication and checking us in. Would definitely stay here again!"
United States
Teresa D.
The price is HK$1,295
HK$1,901 total
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom house on quiet brick and tree lined street.
An outdoor café with tables and chairs arranged under a wooden pergola structure, surrounded by lush greenery.

6. Charming 1-bedroom apartment in downtown historic Weston

Charming 1-bedroom apartment in downtown historic Weston
Weston
9.0 out of 10, Wonderful, (28 reviews)
"Great location. Easy check in!"
United States
Jennifer H.
The price is HK$1,307
HK$1,712 total
includes taxes & fees
21 Oct - 22 Oct
Charming 1-bedroom apartment in downtown historic Weston
A spacious kitchen with a large island, a dining area with a round table, a living room with a fireplace, and a ceiling fan.

7. Pet-Friendly Near Kansas City, Fenced Yard, King Suite, Blackstone

Pet-Friendly Near Kansas City, Fenced Yard, King Suite, Blackstone
Tonganoxie
10.0 out of 10, Exceptional, (5 reviews)
"Clean property, central location, perfect space for 5-6 people."
United States
Addie G.
The price is HK$1,570
HK$3,041 total
includes taxes & fees
8 Nov - 9 Nov
Pet-Friendly Near Kansas City, Fenced Yard, King Suite, Blackstone
A kitchen with wooden cabinets, a white refrigerator, a stove, and a microwave.

8. Terrific Townhome w/fenced in yard and patio

Terrific Townhome w/fenced in yard and patio
Lawrence
9.8 out of 10, Exceptional, (54 reviews)
"This place is well maintained, super clean, and had everything we needed!"
United States
Morgan J.
The price is HK$1,060
HK$2,264 total
includes taxes & fees
15 Oct - 16 Oct
Terrific Townhome w/fenced in yard and patio
A neatly made bed with white linens and patterned pillows, a bedside table with a lamp, and a small wooden side table with baskets.

9. 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, (37 reviews)
"We love staying here! The house was very clean and quaint. We had everything we needed and were able to easily cook our families meals. We would definitely stay again."
United States
Katrina H.
The price is HK$1,703
HK$2,877 total
includes taxes & fees
19 Oct - 20 Oct
Newly Remodeled Classic Old Leavenworth Home in the heart of town
A building with a stone facade, wooden structures, and a paved area with trees and planters.

10. 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, (11 reviews)
"We loved it!"
United States
Jeri B.
The price is HK$3,924
HK$6,572 total
includes taxes & fees
20 Oct - 21 Oct
Spacious 7-bedroom house with WiFi and game room in charming Meriden.
A living room with a sofa, coffee table, and lamps. There is a kitchen area with a dining table and chairs.

11. 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.
The price is HK$3,067
HK$3,778 total
includes taxes & fees
26 Oct - 27 Oct
Wild Feline Retreat
A kitchen with a central island, wooden stools, a refrigerator, a microwave, and hanging pendant lights.

12. Cottage On Main- In The Heart Of Weston

Cottage On Main- In The Heart Of Weston
Weston
8.6 out of 10, Excellent, (133 reviews)
"The breakfast item were nice!"
United States
Leanne L.
The price is HK$1,923
HK$2,367 total
includes taxes & fees
21 Oct - 22 Oct
Cottage On Main- In The Heart Of Weston
A modern kitchen with a brick wall, white cabinetry, and pendant lighting.

13. Wild Equine Loft Apartment

Wild Equine Loft Apartment
Weston
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful property. I would stay there again. Perfect location."
United States
Jennifer
The price is HK$3,067
HK$3,778 total
includes taxes & fees
26 Oct - 27 Oct
Wild Equine Loft Apartment
A wooden building with a covered entrance, stone pillars, and outdoor seating.

14. 2 BDR Finished Basement, Fitness Room, Kitchen, 1.5 Bath Pool, Hot Tub May-Sep

2 BDR Finished Basement, Fitness Room, Kitchen, 1.5 Bath Pool, Hot Tub May-Sep
Weston
10.0 out of 10, Exceptional, (1 review)
"The property was clean and had all the amenities that we were looking for"
United States
Eric S.
The price is HK$1,856
HK$2,699 total
includes taxes & fees
15 Oct - 16 Oct
2 BDR Finished Basement, Fitness Room, Kitchen, 1.5 Bath Pool, Hot Tub May-Sep
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

TownePlace Suites by Marriott Leavenworth

TownePlace Suites by Marriott Leavenworth

10/10 Excellent
"Great staff."
Ahren 1-night trip
Posted 22 hours ago
TownePlace Suites by Marriott Leavenworth

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

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?

Historical home w gardens in Unique North Lawrence. ACROSS FROM TRAIN DEPOT: This holiday home rental outside of Winchester offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Perry Lake Recreation Area and Atchison County Historical Society Museum.

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.