Winchester Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

Leavenworth Local Hotel

2.5 star property
8.8 out of 10, Excellent, (333)
"This is our second time to stay and both times the stay was wonderful. The rooms are spacious and clean. They also have friendly helpful staff"
The price is AU$175
includes taxes & fees
15 Sept - 16 Sept
Leavenworth Local Hotel

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

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 AU$608
includes taxes & fees
16 Sept - 17 Sept
Historic David Brewer Victorian

Cottage On Main- In The Heart Of Weston

8.8 out of 10, Excellent, (104)
"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 AU$460
includes taxes & fees
11 Sept - 12 Sept
Cottage On Main- In The Heart Of Weston

Wild Equine Loft Apartment

10.0 out of 10, Exceptional, (14)
"Incredible property in a great location in Weston. "
The price is AU$646
includes taxes & fees
15 Sept - 16 Sept
Wild Equine Loft Apartment

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

The price is AU$265
includes taxes & fees
6 Oct - 7 Oct
The Batch - Tiny House Living On 40 Acres

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.

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 AU$447
includes taxes & fees
11 Sept - 12 Sept
Secluded Cabin near Lake Perry

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

9.8 out of 10, Exceptional, (57)
"My husband and I stayed for our anniversary and it was exactly as promised - short walk to all Weston has to offer, cozy inside, and the food provided was delicious!"
The price is AU$386
includes taxes & fees
14 Sept - 15 Sept
Marr Manor - Studio B&B downtown

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

10.0 out of 10, Exceptional, (57)
"Wonderful stay. Highly recommend"
Fully Renovated Historic Home with bluff views of Missouri River & Valley

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

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 AU$327
includes taxes & fees
11 Sept - 12 Sept
Charming 2-bedroom house in Atchison on quiet brick and tree lined street.

Bee & Bee Bungalow - Studio B&B downtown

10.0 out of 10, Exceptional, (27)
"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 AU$359
includes taxes & fees
16 Sept - 17 Sept
Bee & Bee Bungalow - Studio B&B downtown

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!

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!

10.0 out of 10, Exceptional, (43)
"Great property in great peaceful location even had some toys there for the kids"
Visit the farm!

Wild Feline Retreat

10.0 out of 10, Exceptional, (11)
"We stayed her with some friends for a fun weekend. Great location and great place to stay! "
The price is AU$646
includes taxes & fees
15 Sept - 16 Sept
Wild Feline Retreat

Charming 1-bedroom apartment in downtown historic Weston

9.4 out of 10, Exceptional, (12)
"This mother-in-law suite was clean and cozy, and within easy walking distance to the restaurants and shops."
The price is AU$330
includes taxes & fees
14 Sept - 15 Sept
Charming 1-bedroom apartment in downtown historic Weston
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$175 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Historic David Brewer Victorian: This holiday home rental outside of Winchester 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 that 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 wider area, you’ll find Perry Lake Recreation Area and Delaware State Park.

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.