Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Exterior
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
10.0 out of 10, Exceptional, (243)
"Our group of old ladies (we range 55-74) stayed here for a weekend getaway. It was the best place we've every been. The kitchen has everything you could need to prepare anything! Just walking in the front door we were awe struck by the spaciousness and the welcoming feeling of the cabin. It was clean, comfortable, quiet and just what we were looking for. We can hardly wait to go back again."
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
Property grounds
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
10.0 out of 10, Exceptional, (308)
"This is a wonderful property. Quiet, serene, spotless, welcoming."
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
Fridge, microwave, oven, stovetop
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
10.0 out of 10, Exceptional, (97)
"This cabin was perfect for my husband and I and my daughter and two grandsons. It was equipped with everything we needed. We spent alot of time at the lake fishing, having coffee in the morning listening to the wildlife and also having a fire each night. Even the firewood was provided. I highly recommend this cabin and we will definitely be back!"
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
Hunter Lodge (Secluded in Amish Country and peaceful)
Marina
Hunter Lodge (Secluded in Amish Country and peaceful)
10.0 out of 10, Exceptional, (20)
"Clean, comfortable and quiet. We enjoyed our stay very much."
The price is €164
includes taxes & fees
30 Jun - 1 Jul
Hunter Lodge (Secluded in Amish Country and peaceful)
The Bear Den (Secluded in Amish Country and peaceful)
Fridge, microwave, oven, stovetop
The Bear Den (Secluded in Amish Country and peaceful)
10.0 out of 10, Exceptional, (17)
"Very clean and quiet…perfect for birding and relaxing!"
The price is €164
includes taxes & fees
30 Jun - 1 Jul
The Bear Den (Secluded in Amish Country and peaceful)
Amish-built cabin, serene and peaceful with pond and private dock for fishing.
2 bedrooms, bed sheets
Amish-built cabin, serene and peaceful with pond and private dock for fishing.
10.0 out of 10, Exceptional, (10)
"Quiet. Peaceful. Stunning sunset and sunrise views. Close to good hiking including Quiveringhearts. The owner was delightfully accessible as was her employee. The cats were a handful but we got used to them. They calmed down after they were fed understandably!"
Amish-built cabin, serene and peaceful with pond and private dock for fishing.
Cowboy Saloon Cabin
Property grounds
Cowboy Saloon Cabin
9.8 out of 10, Exceptional, (6)
"This tiny house was perfect for my sister in law and I. We had an event in Georgetown and this location was close and easy. There were no softball games while we were there, but if there were games it would be a very different stay as it is about 10 feet from the field. For us, it was quiet and lovely. I had booked one of the other cabins that didn't have a restroom and Pamela was WONDERFUL to work with and change us to a cabin with a restroom. I would definitely stay at this property again."
The price is €163
includes taxes & fees
1 Jul - 2 Jul
Cowboy Saloon Cabin
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
Property grounds
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
10.0 out of 10, Exceptional, (14)
"My husband and I stayed here Father’s Day weekend with 90° temps. Instead of camping, we decided to stay here and we were well taken care of! The place was well stocked Inside and out. Propane grill is ready to go &firewood ready for the fire pit. Inside was comfortable, easy to relax with the AC along with friendly and well-behaved canines visiting. ♥️ Ken and Cindy are nearby if there are any needs but absolutely gave us the space on our own to enjoy!! The area is as real rural as it gets with...
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Oven, stovetop, dishwasher
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
10.0 out of 10, Exceptional, (13)
"For the last four years, we have a family weekend with 14-18 people. We've rented a different place every year. This has been by far the best place for our group. The place really is massive. We could have comfortably fit another 4-6 people. Instead of people sleeping 4 in a room, each group had their own space. The common areas are large, and there's a nice outdoor area with a fire pit. If you have a large group, it doesn't get much better than this. The only con is really that it's close to...
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Property grounds
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
10.0 out of 10, Exceptional, (55)
"Our 2nd Fall stay here and another great time!! 16 guys and plenty of room for all. Great yard space for cornhole & can jam. Love the fire ring. Some rain our last night, but plenty of room inside for card games. GREAT PLACE!! GREAT DEAL!!"
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Lazy Spread Cabin. Secluded wooded cabin tucked away with all the amenities
Exterior
Lazy Spread Cabin. Secluded wooded cabin tucked away with all the amenities
10.0 out of 10, Exceptional, (9)
"Our stay at Lazy Spread Cabin was nothing short of exceptional. Tucked away in a serene rural area, this cabin offers everything you could possibly need for a relaxing getaway. Firstly, the cabin is impressively well-equipped with all the comforts of home and more. From the meticulously clean spa and outdoor fire pit to the spacious sitting areas and comfortable beds, every detail is carefully thought out. The bbq was clean and with it we made some yummy hamburgers. The location is...
The price is €165
includes taxes & fees
15 Jul - 16 Jul
Lazy Spread Cabin. Secluded wooded cabin tucked away with all the amenities
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
Exterior
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
10.0 out of 10, Exceptional, (15)
"My yearly extended family get together was very enjoyable at this beautiful property. The swimming pond was most appreciated in the summer heat and the water temp was perfect, not too warm nor cold. The kitchen is well stocked, the outdoor bar / grill with direct TV and fire pit was a great gathering spot. The location is a little remote, but still an easy drive to Serpent Mound, hiking, breweries, wineries, Portsmouth Murals, and the world's largest horseshoe crab in Hillsboro!"
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
URBAN GETAWAY - .6 Downtown Maysville/Entire House
Property grounds
URBAN GETAWAY - .6 Downtown Maysville/Entire House
9.8 out of 10, Exceptional, (16)
"We had everything we needed, and enjoyed the house a lot! The house is beautiful, while still keeping its old charm."
The price is €118
includes taxes & fees
9 Jul - 10 Jul
URBAN GETAWAY - .6 Downtown Maysville/Entire House
Your luxury cottage in the country - Murphin Ridge - Amish built
View from property
Your luxury cottage in the country - Murphin Ridge - Amish built
9.8 out of 10, Exceptional, (86)
"Great stay in a beautifully designed and appointed space. Modern and tranquil. All the windows bring the sites and the sounds of nature inside. Will definitely be back."
The price is €220
includes taxes & fees
15 Jul - 16 Jul
Your luxury cottage in the country - Murphin Ridge - Amish built
SECLUDED PARADISE! 3-Lvl Home on 8 Acres in Amish Country! 4 Bedrms/3 Full Baths
Property grounds
SECLUDED PARADISE! 3-Lvl Home on 8 Acres in Amish Country! 4 Bedrms/3 Full Baths
9.8 out of 10, Exceptional, (121)
"We appreciated our stay at The Sanctuary. The host was very on point with response times and providing "key" information. Easy check-in process. Host was very helpful with accommodation needs, providing good space for our family. Very nice kitchen, well-equipped and functional. Very clean with comfortable beds. Free Wi-Fi available, limitations on use, definitely a place to "unplug". Family certainly enjoyed their stay at The Sanctuary."
SECLUDED PARADISE! 3-Lvl Home on 8 Acres in Amish Country! 4 Bedrms/3 Full Baths
Newly renovated unit in downtown Maysville’s Entertainment District.
Property grounds
Newly renovated unit in downtown Maysville’s Entertainment District.
10.0 out of 10, Exceptional, (23)
"Enjoyed our visit and accommodations! Spacious, clean and great location! Will definitely check on this property’s availability the next time we visit!"
Newly renovated unit in downtown Maysville’s Entertainment District.
Flash Lodge Add-on Cabin-Pamela's Diamond
Exterior
Flash Lodge Add-on Cabin-Pamela's Diamond
9.4 out of 10, Exceptional, (21)
"Very nice very hard to find"
The price is €128
includes taxes & fees
7 Jul - 8 Jul
Flash Lodge Add-on Cabin-Pamela's Diamond
Private cabin on 80 acre farm in Adams County Ohio
1 bedroom, bed sheets
Private cabin on 80 acre farm in Adams County Ohio
10.0 out of 10, Exceptional, (7)
"We had a lovely time in this cozy cabin. Just what we needed to unplug and unwind for a delightful weekend. Hosts were communicative and helpful and we will likely stay again if we come to the area."
Private cabin on 80 acre farm in Adams County Ohio
Secluded cabin located in Amish country
Property grounds
Secluded cabin located in Amish country
10.0 out of 10, Exceptional, (68)
"This place was perfect for a peaceful weekend getaway trip. Easy to find and everything inside was so cozy and clean. Plenty of state parks and hiking trails around the area, would definitely come back again and explore more!"
Secluded cabin located in Amish country
Peaceful Getaway! Amish-Built, 6 Private Acres & Stocked Pond--All Amenities!!
Exterior
Peaceful Getaway! Amish-Built, 6 Private Acres & Stocked Pond--All Amenities!!
10.0 out of 10, Exceptional, (102)
"so beautiful and peaceful!"
Peaceful Getaway! Amish-Built, 6 Private Acres & Stocked Pond--All Amenities!!
Don't see what you're looking for?
See all available properties in Winchester
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.

Other types of properties in Winchester you may be interested in

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Exterior
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
10.0 out of 10, Exceptional, (243)
"Our group of old ladies (we range 55-74) stayed here for a weekend getaway. It was the best place we've every been. The kitchen has everything you could need to prepare anything! Just walking in the front door we were awe struck by the spaciousness and the welcoming feeling of the cabin. It was clean, comfortable, quiet and just what we were looking for. We can hardly wait to go back again."
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Countryside Inn & Suites
Lobby sitting area
Countryside Inn & Suites
2.5 star property
7.0 out of 10, Good, (412)
"Great option for proximity to East Fork State Park "
The price is €104
includes taxes & fees
2 Jul - 3 Jul
Countryside Inn & Suites
French Quarter Inn
Front of property
French Quarter Inn
3.0 star property
8.8 out of 10, Excellent, (635)
"The in room whirlpool did not work. The mattress was old No drinking water available No hot breakfast Tuesday morning "
The price is €103
includes taxes & fees
9 Jul - 10 Jul
French Quarter Inn
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.

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, apart-hotels, 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 favorite 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 depends 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 €118 per night. Entering your travel dates in the search wizard you might find 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 holiday rentals 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?

The Manor at Maysville Golf Course View: This holiday home rental outside of Winchester is located next to a golf course, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Winchester?

While you're exploring the area, Adams Lake State Park and Rocky Fork Lake State Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Serpent Mound and Rocky Fork Lake.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.

Recent reviews of Winchester properties
Expedia verified reviews

Quality Inn

Quality Inn

5/5 Excellent
"Best hotel "
A verified traveller stayed at Quality Inn
Posted 2 days ago
Quality Inn