Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Winchester

Our top choices for Winchester vacation rentals

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

Leavenworth Local Hotel

2.5 star property
8.8 out of 10, Excellent, (331)
"Great Location very walkable "
The price is ￥14,564
￥17,112 total
includes taxes & fees
Sep 8 - Sep 9
Leavenworth Local Hotel
Condotels
Front of property

Condotels

3.0 star property
9.0 out of 10, Wonderful, (185)
"Great location in a safe neighborhood. Love the walking trail and fountain nearby."
Condotels
Historic David Brewer Victorian
Fridge, microwave, oven, stovetop

Historic David Brewer Victorian

10.0 out of 10, Exceptional, (7)
"This is a beautiful, historic home that is comfortable and welcoming. The decor and information provided about the rooms and former residents was very interesting. We enjoyed our stay! "
The price is ￥31,535
￥63,780 total
includes taxes & fees
Sep 8 - Sep 9
Historic David Brewer Victorian
Cottage On Main- In The Heart Of Weston
Fridge, microwave, oven, stovetop

Cottage On Main- In The Heart Of Weston

8.8 out of 10, Excellent, (103)
"Enjoyed this sweet city. This rental was very nice. Beds very comfortable, breakfast items very plentiful, well stocked paper products. Very close to stores and restaurants. Owner was very helpful, great rental for 5 ladies. "
The price is ￥36,272
￥44,356 total
includes taxes & fees
Sep 7 - Sep 8
Cottage On Main- In The Heart Of Weston
Wild Equine Loft Apartment
Stovetop

Wild Equine Loft Apartment

10.0 out of 10, Exceptional, (14)
"Absolutely loved the place! Better than the listing even described and fantastic service from the owners. Highly recommend!"
The price is ￥51,669
￥62,832 total
includes taxes & fees
Sep 10 - Sep 11
Wild Equine Loft Apartment
The Guest House on Seneca with King Bed
Terrace/patio

The Guest House on Seneca with King Bed

10.0 out of 10, Exceptional, (5)
"Stayed twice-Nice place & great host!!"
The Guest House on Seneca with King Bed
The Batch - Tiny House Living On 40 Acres
Terrace/patio

The Batch - Tiny House Living On 40 Acres

The price is ￥16,926
￥25,619 total
includes taxes & fees
Sep 8 - Sep 9
The Batch - Tiny House Living On 40 Acres
Quaint house on the bluffs overlooking the scenic Missouri River.
Property grounds

Quaint house on the bluffs overlooking the scenic Missouri River.

10.0 out of 10, Exceptional, (38)
"Marvelous location with an amazing view of the river"
Quaint house on the bluffs overlooking the scenic Missouri River.
Fully Renovated Historic Home with bluff views of Missouri River & Valley
Exterior

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

10.0 out of 10, Exceptional, (55)
"Wonderful stay. Highly recommend"
Fully Renovated Historic Home with bluff views of Missouri River & Valley
Secluded Cabin near Lake Perry
Fridge, microwave, oven, stovetop

Secluded Cabin near Lake Perry

9.0 out of 10, Wonderful, (2)
"Very nice the owners have thought about everything! We were very impressed of the inside of the house. Highly recommend!"
The price is ￥18,559
￥43,261 total
includes taxes & fees
Sep 7 - Sep 8
Secluded Cabin near Lake Perry
The Landing is a Cheerful 3 bedroom 2 bath home!
Fridge, microwave, oven, stovetop

The Landing is a Cheerful 3 bedroom 2 bath home!

10.0 out of 10, Exceptional, (32)
"Enjoyed our stay! "
The Landing is a Cheerful 3 bedroom 2 bath home!
Marr Manor - Studio B&B downtown
1 bedroom, iron/ironing board, WiFi, bed sheets

Marr Manor - Studio B&B downtown

9.8 out of 10, Exceptional, (56)
"We have stayed several times and have never been disappointed"
The price is ￥28,870
￥37,407 total
includes taxes & fees
Sep 10 - Sep 11
Marr Manor - Studio B&B downtown
Charming 2-bedroom house in Atchison on quiet brick and tree lined street.
Fridge, microwave, oven, stovetop

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"This property is newly renovated and very clean. The owner was very easy to communicate with and made our stay in Atchison great. Highly recommend!"
The price is ￥21,467
￥32,264 total
includes taxes & fees
Sep 10 - Sep 11
Charming 2-bedroom house in Atchison on quiet brick and tree lined street.
Bee & Bee Bungalow - Studio B&B downtown
1 bedroom, iron/ironing board, WiFi, bed sheets

Bee & Bee Bungalow - Studio B&B downtown

10.0 out of 10, Exceptional, (26)
"What a perfect place to stay in Weston! Very clean and it had everything we needed. The owners went above and beyond to make our stay very memorable!!"
The price is ￥28,870
￥35,137 total
includes taxes & fees
Sep 10 - Sep 11
Bee & Bee Bungalow - Studio B&B downtown
Family-Friendly Lansing Home with Covered Balcony!
Coffee/tea maker, highchair, cookware/dishes/utensils

Family-Friendly Lansing Home with Covered Balcony!

8.6 out of 10, Excellent, (11)
"Everything was perfect, and the location for every place we needed to go was awesome Thank You "
Family-Friendly Lansing Home with Covered Balcony!
Historical home w gardens in Unique North Lawrence. ACROSS FROM TRAIN DEPOT
Terrace/patio

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

10.0 out of 10, Exceptional, (1)
"Great location! Convenient to downtown and all of Lawrence. I used to live downtown so I know about the trains. Yes you can hear them as it clearly states in the description. We actually liked the rumble of the trains after the horns. Home is great with everything anyone could need. Great courtyard that I imagine in the spring is bloomed and beautiful. Host was easy to communicate with and very responsive. If trains bother you don’t stay here but if you know Lawrence you know this is a great...
Historical home w gardens in Unique North Lawrence. ACROSS FROM TRAIN DEPOT
NEW! Fully Remodeled 1910 Craftsman Style Home
Fridge, microwave, oven, stovetop

NEW! Fully Remodeled 1910 Craftsman Style Home

10.0 out of 10, Exceptional, (32)
"This house is perfect for our family of 9. Plenty of room and feels like home! We have stayed here multiple times! "
NEW! Fully Remodeled 1910 Craftsman Style Home
The Black Thistle a historical church in downtown Tonganoxie!
Dining

The Black Thistle a historical church in downtown Tonganoxie!

10.0 out of 10, Exceptional, (16)
"Great place to stay, highly recommend. "
The Black Thistle a historical church in downtown Tonganoxie!
Visit the farm!
Interior

Visit the farm!

10.0 out of 10, Exceptional, (42)
"We stayed at this lovely farm house for Benedictine graduation weekend. Its 20 min from Atchison on back country roads. It was beautiful inside and out. Christine made us feel so welcome and provided everything we needed. Wish we could stay longer."
Visit the farm!
Wild Feline Retreat
3 bedrooms, WiFi, bed sheets

Wild Feline Retreat

10.0 out of 10, Exceptional, (11)
"Melissa was an amazing host and the homemade blueberry muffins were spectacular and such a wonderful touch! "
The price is ￥51,669
￥62,832 total
includes taxes & fees
Sep 10 - Sep 11
Wild Feline Retreat
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

Find out more about Winchester

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:

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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?

Historic David Brewer Victorian: Visitors like this Winchester vacation home rental. It is near skiing and equipped with air-conditioning and laundry facilities 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.

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 Delaware State Park.

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.