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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester vacation rentals

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

1. Leavenworth Local Hotel

Leavenworth Local Hotel
2.5 star property
Leavenworth
8.8 out of 10, Excellent, (445 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 AED 289
AED 339 total
includes taxes & fees
11 Oct - 12 Oct
Leavenworth Local Hotel
Smart TV, fireplace, stereo

2. 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 AED 331
AED 521 total
includes taxes & fees
27 Oct - 28 Oct
Country Living on 32 Acre Farm
Property grounds

3. 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 AED 653
AED 785 total
includes taxes & fees
30 Sep - 1 Oct
Cozy Cabin Rental on Sacred Land Ideal for Glamping in Kansas
Smart TV

4. 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, (23 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.
The price is AED 478
AED 900 total
includes taxes & fees
3 Oct - 4 Oct
Farmhouse on the Prairie - You can see for miles!
Interior

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, (23 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 AED 628
AED 897 total
includes taxes & fees
29 Sep - 30 Sep
Charming 2-bedroom house on quiet brick and tree lined street.
Outdoor dining

6. Charming 1-bedroom apartment in downtown historic Weston

Charming 1-bedroom apartment in downtown historic Weston
Weston
9.2 out of 10, Wonderful, (24 reviews)
"Great location. Easy check in!"
United States
Jennifer H.
The price is AED 612
AED 773 total
includes taxes & fees
28 Sep - 29 Sep
Charming 1-bedroom apartment in downtown historic Weston
Interior

7. 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)
"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
The price is AED 779
AED 1,257 total
includes taxes & fees
8 Oct - 9 Oct
Newly Remodeled Classic Old Leavenworth Home in the heart of town
Coffee/tea maker, fridge, microwave, oven

8. Terrific Townhome w/fenced in yard and patio

Terrific Townhome w/fenced in yard and patio
Lawrence
10.0 out of 10, Exceptional, (53 reviews)
"This place is well maintained, super clean, and had everything we needed!"
United States
Morgan J.
The price is AED 496
AED 1,023 total
includes taxes & fees
28 Sep - 29 Sep
Terrific Townhome w/fenced in yard and patio
Exterior detail

9. Dual patios, Free Laundry Service, College steps, 2BR 1 BA

Dual patios, Free Laundry Service, College steps, 2BR 1 BA
Atchison
10.0 out of 10, Exceptional, (1 review)
"So appreciate the location and availability of this place. It served our needs perfectly. We even had a place to grill a couple of meals!"
United States
Jennifer P.
The price is AED 903
AED 1,333 total
includes taxes & fees
27 Oct - 28 Oct
Dual patios, Free Laundry Service, College steps, 2BR 1 BA
Coffee/tea maker, fridge, microwave, oven

10. 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 AED 900
AED 1,044 total
includes taxes & fees
30 Sep - 1 Oct
Cottage On Main- In The Heart Of Weston
Dining

11. Benedictine Theme 2br 1ba

Benedictine Theme 2br 1ba
Atchison
8.8 out of 10, Excellent, (6 reviews)
"Great location and space for visiting family to BC student. Host was fantastic! The backyard deck was perfect for morning coffee! We will be back!"
United States
KIMBERLY S.
The price is AED 1,041
AED 1,504 total
includes taxes & fees
29 Sep - 30 Sep
Benedictine Theme 2br 1ba
TV

12. 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 AED 1,410
AED 1,635 total
includes taxes & fees
28 Sep - 29 Sep
Wild Feline Retreat
Interior

13. countryside Victorian getaway Save

countryside Victorian getaway Save
Basehor
The price is AED 380
AED 666 total
includes taxes & fees
8 Oct - 9 Oct
countryside Victorian getaway Save
Interior

14. 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, (4 reviews)
"This place was great and enjoyable stay for the group we had. In a quiet little area and close enough to the city but still far enough away to be out."
United States
Jesse M.
The price is AED 900
AED 1,548 total
includes taxes & fees
22 Oct - 23 Oct
Pet-Friendly Near Kansas City, Fenced Yard, King Suite, Blackstone
Coffee/tea maker, fridge, microwave, oven

15. 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 AED 1,410
AED 1,635 total
includes taxes & fees
28 Sep - 29 Sep
Wild Equine Loft Apartment
Property grounds

16. 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 AED 1,837
AED 2,892 total
includes taxes & fees
27 Oct - 28 Oct
Spacious 7-bedroom house with WiFi and game room in charming Meriden.
Exterior

17. 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
The price is AED 869
AED 1,197 total
includes taxes & fees
28 Sep - 29 Sep
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

Hampton Inn Leavenworth

Hampton Inn Leavenworth

8/10 Good
"Staff was very helpful--allowed me to check in two hours early. Good security in the building after dark--doors locked and need to use card for access after 10:00 PM. Staff helpful in recommending good, nearby places to eat. Room was clean. Breakfast was adequate but not spectacular--having bacon or sausage patties would have been a big plus."
John 1-night trip
Posted 7 hours ago
Hampton Inn Leavenworth

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?

Historical home w gardens in Unique North Lawrence. ACROSS FROM TRAIN DEPOT: Visitors like this Winchester vacation home rental. It 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 you can cook with friends or family. Make the most of the selection 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 The Sallie House, 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.