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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winchester vacation rentals

Interior

1. countryside Victorian getaway Save

countryside Victorian getaway Save
Basehor
The price is SAR 368
SAR 771 total
includes taxes & fees
24 Aug - 25 Aug
countryside Victorian getaway Save
Room, 1 King Bed, Non Smoking | Premium bedding, down comforters, desk, laptop workspace

2. Leavenworth Local Hotel

Leavenworth Local Hotel
2.5 star property
Leavenworth
8.8 out of 10, Excellent, (423 reviews)
"Excellent staff and location"
United States
Catherine
The price is SAR 331
SAR 390 total
includes taxes & fees
26 Aug - 27 Aug
Leavenworth Local Hotel
Coffee/tea maker, fridge, microwave, oven

3. 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 SAR 443
SAR 1,077 total
includes taxes & fees
16 Aug - 17 Aug
Secluded Cabin near Lake Perry
Smart TV, fireplace, stereo

4. 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 SAR 375
SAR 573 total
includes taxes & fees
16 Aug - 17 Aug
Country Living on 32 Acre Farm
Property grounds

5. 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 SAR 644
SAR 796 total
includes taxes & fees
16 Aug - 17 Aug
Cozy Cabin Rental on Sacred Land Ideal for Glamping in Kansas
Interior

6. 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, (3 reviews)
"Clean property, central location, perfect space for 5-6 people."
United States
Addie G.
The price is SAR 1,033
SAR 1,834 total
includes taxes & fees
21 Aug - 22 Aug
Pet-Friendly Near Kansas City, Fenced Yard, King Suite, Blackstone
Outdoor dining

7. Charming 1-bedroom apartment in downtown historic Weston

Charming 1-bedroom apartment in downtown historic Weston
Weston
9.0 out of 10, Wonderful, (21 reviews)
"Great location. Easy check in!"
United States
Jennifer H.
The price is SAR 625
SAR 812 total
includes taxes & fees
20 Aug - 21 Aug
Charming 1-bedroom apartment in downtown historic Weston
Coffee/tea maker, fridge, microwave, oven

8. Cottage On Main- In The Heart Of Weston

Cottage On Main- In The Heart Of Weston
Weston
8.8 out of 10, Excellent, (129 reviews)
"The breakfast item were nice!"
United States
Leanne L.
The price is SAR 920
SAR 1,124 total
includes taxes & fees
23 Aug - 24 Aug
Cottage On Main- In The Heart Of Weston
Interior

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, (35 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 SAR 792
SAR 1,367 total
includes taxes & fees
2 Sep - 3 Sep
Newly Remodeled Classic Old Leavenworth Home in the heart of town
TV

10. 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 SAR 1,441
SAR 1,750 total
includes taxes & fees
17 Aug - 18 Aug
Wild Feline Retreat
Exterior detail

11. 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 SAR 923
SAR 1,449 total
includes taxes & fees
9 Sep - 10 Sep
Dual patios, Free Laundry Service, College steps, 2BR 1 BA
Exterior

12. 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.
Weston Home perfectly located. Walk from the house and explore town!
Coffee/tea maker, fridge, microwave, oven

13. Terrific Townhome w/fenced in yard and patio

Terrific Townhome w/fenced in yard and patio
Lawrence
9.8 out of 10, Exceptional, (50 reviews)
"This place is well maintained, super clean, and had everything we needed!"
United States
Morgan J.
The price is SAR 507
SAR 1,098 total
includes taxes & fees
17 Aug - 18 Aug
Terrific Townhome w/fenced in yard and patio
Smart TV

14. 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, (20 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 SAR 311
SAR 744 total
includes taxes & fees
16 Aug - 17 Aug
Farmhouse on the Prairie - You can see for miles!
Interior

15. 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
The price is SAR 507
SAR 908 total
includes taxes & fees
14 Aug - 15 Aug
Clean, easily accessible 2bdrm apartment with AC. 2 mins to base - 15mins to KC
Stovetop

16. Wild Equine Loft Apartment

Wild Equine Loft Apartment
Weston
10.0 out of 10, Exceptional, (32 reviews)
"Great Place"
United States
Joe H.
The price is SAR 1,441
SAR 1,761 total
includes taxes & fees
19 Aug - 20 Aug
Wild Equine Loft Apartment
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 SAR 960
SAR 1,378 total
includes taxes & fees
15 Aug - 16 Aug
2 BDR Finished Basement, Fitness Room, Kitchen, 1.5 Bath Pool, Hot Tub May-Sep
Property grounds

18. 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, (10 reviews)
"We loved it!"
United States
Jeri B.
The price is SAR 1,877
SAR 3,144 total
includes taxes & fees
26 Aug - 27 Aug
Spacious 7-bedroom house with WiFi and game room in charming Meriden.
Interior

19. 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, (22 reviews)
"Great place in a nice neighborhood. The host is very friendly and helpful!"
United States
Nathan D.
The price is SAR 558
SAR 837 total
includes taxes & fees
26 Aug - 27 Aug
Charming 2-bedroom house on quiet brick and tree lined street.
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

Leavenworth Local Hotel

Leavenworth Local Hotel

8/10 Good
"I feel that the Local punches above it's weight, the room was comfortable and spacious. The free breakfast was a disappointment. We enjoyed the large windows that room #211 provided us. It was a great view of the world of Leavenworth. The train whistle was charming to hear. The staff was gracious. We are certain to return."
herbert 3-night trip
Posted 9 hours ago
Leavenworth Local Hotel

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 Nell Hill's, or get outside and enjoy nature at Perry Lake. In the larger area, you’ll find Perry Lake Recreation Area and International Forest of Friendship.

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.