Winchester Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Winchester

Exterior
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
10.0 out of 10, Exceptional, (240)
"Everything was great. your not far from the amish bakery or meat markets. went for serpent mound. the lake on the property is gorgeous, its just a 1/4 mile away and up a step hill. my dad couldn't walk it but if you can make it it is very nice. kitchen is great. showers are good too."
Rustic Cabin with modern amenities and 1 acre stocked 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, (95)
"The cabin was beautiful and the cleanest place we have ever rented. Very well stocked, wonderful outdoor space. The host was very friendly, quickly responsive to any needs or questions. We really enjoyed our stay and hope to go back."
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
Fridge, microwave, oven, stovetop
The Bear Den (Secluded in Amish Country and peaceful)
10.0 out of 10, Exceptional, (16)
"Everything was wonderful!"
The price is ￥16,459
￥26,648 total
includes taxes & fees
May 26 - May 27
The Bear Den (Secluded in Amish Country and peaceful)
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
Beautiful Rocky Fork 2BR Cozy Cottage
10.0 out of 10, Exceptional, (87)
"We really enjoyed our stay in this cute little cottage. Great location and Robin was very helpful during our stay. Would definitely recommend and stay here again!"
Beautiful Rocky Fork 2BR Cozy Cottage
Property grounds
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
10.0 out of 10, Exceptional, (307)
"This is a wonderful property. Quiet, serene, spotless, welcoming."
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
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 ￥19,594
￥26,648 total
includes taxes & fees
May 26 - May 27
Cowboy Saloon Cabin
1 bedroom, bed sheets
Private cabin on 80 acre farm in Adams County Ohio
10.0 out of 10, Exceptional, (6)
"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
Oven, stovetop, dishwasher
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
10.0 out of 10, Exceptional, (12)
"We had a great weekend. The owner was very responsive and the house and property was beautiful."
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Exterior
Flash Lodge Add-on Cabin-Pamela's Diamond
9.6 out of 10, Exceptional, (19)
"Thanks for the stay!"
The price is ￥13,637
￥20,691 total
includes taxes & fees
May 25 - May 26
Flash Lodge Add-on Cabin-Pamela's Diamond
Exterior
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
10.0 out of 10, Exceptional, (12)
"This allowed all my brothers and sister along with grandchildren to enjoy each others company!!"
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
3 bedrooms, desk, iron/ironing board, WiFi
Beautifully renovated 3BR house w/lake views
10.0 out of 10, Exceptional, (16)
"Perfect size and location for our getaway. The gameroom was great for the kids, great fire pit for the adults. Close to all that Rocky Fork has to offer."
Beautifully renovated 3BR house w/lake views
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
Exterior
Lazy Spread Cabin. Secluded wooded cabin tucked away with all the amenities
10.0 out of 10, Exceptional, (8)
"Amazing property. Has everything you'd want in a rental."
Lazy Spread Cabin. Secluded wooded cabin tucked away with all the amenities
View from property
Your luxury cottage in the country - Murphin Ridge - Amish built
9.8 out of 10, Exceptional, (84)
"Beautiful space. No TV or internet , but that was okay! We did find a few large black ants and mouse poop on a bed pillow. But hey, we are so close to nature. Would definitely stay if in the are again. ✌Pam"
The price is ￥20,378
￥35,998 total
includes taxes & fees
May 30 - May 31
Your luxury cottage in the country - Murphin Ridge - Amish built
Property grounds
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
10.0 out of 10, Exceptional, (10)
"We really enjoyed our weekend here. It was great for the four of us and lots of trails near by to hike."
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
Spa
Rustic Lodge with private cabins / 6 person hot tub and camp fire
10.0 out of 10, Exceptional, (21)
"The home is Beautiful. Everything a family needs is there. Board games, darts, karaoke, corn hole, and steaming TV services. The location is convenient to local attractions. The two individual cabins are very cozy and well appointed. We had a couple small issues that the hosts took care of immediately. A bathroom in the upstairs of the home would be a great addition. We would highly recommend this property."
Rustic Lodge with private cabins / 6 person hot tub and camp fire
Property grounds
Secluded cabin located in Amish country
10.0 out of 10, Exceptional, (66)
". . . because this place is such a treasure, we don't want the secret to get out. If it gets too popular, it'll be hard to book again - and we're definitely booking again! Great location, clean, well-outfitted, QUIET and just simply delightful. When you're ready to relax, unwind and unplug, this is your sweet spot."
Secluded cabin located in Amish country
Marina
Hunter Lodge (Secluded in Amish Country and peaceful)
10.0 out of 10, Exceptional, (17)
"We enjoyed our stay at Hunter Lodge. Cabin was clean and comfortable. Great place to stay while hiking in the area."
The price is ￥16,459
￥26,648 total
includes taxes & fees
May 26 - May 27
Hunter Lodge (Secluded in Amish Country and peaceful)
Property grounds
Nature's Nook Cabin
9.8 out of 10, Exceptional, (71)
"This place is amazing if your looking to get away from everything but who your with this is the place. It’s out of a Norman Rockwell painting the log cabin interior to the recurring bear theme. The bed is super comfortable hot tub grill and snacks round out the welcome home feel. We will definitely stay again. "
Nature's Nook Cabin
Property grounds
Hippie Soul - Entertainment District .2 Downtown Maysville<br>
9.8 out of 10, Exceptional, (9)
"Hippie Soul is a charming, beautiful property. It's well appointed & very comfortable. What a wonderful location. I'd absolutely stay here again."
The price is ￥13,167
￥20,762 total
includes taxes & fees
May 31 - Jun 1
Hippie Soul - Entertainment District .2 Downtown Maysville<br>
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

Exterior
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
10.0 out of 10, Exceptional, (240)
"Everything was great. your not far from the amish bakery or meat markets. went for serpent mound. the lake on the property is gorgeous, its just a 1/4 mile away and up a step hill. my dad couldn't walk it but if you can make it it is very nice. kitchen is great. showers are good too."
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Lobby sitting area
Countryside Inn & Suites
2.5 star property
7.0 out of 10, Good, (397)
"Carpets in hallway was nasty had food grass mud.etc. bed was hard as a rock and sounds like your crunching aluminum cans when you turn over or any kind of movement "
The price is ￥13,518
￥15,309 total
includes taxes & fees
Jun 3 - Jun 4
Countryside Inn & Suites
Front of property
French Quarter Inn
3.0 star property
8.8 out of 10, Excellent, (625)
"Great location "
The price is ￥15,518
￥17,272 total
includes taxes & fees
Jun 9 - Jun 10
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.

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:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals close to top attractions in Winchester, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals that Winchester has to offer?

Beautiful Rocky Fork 2BR Cozy Cottage: Visitors like this Winchester vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like 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 larger area, you’ll find Serpent Mound and Rocky Fork State Park.

What’s a vacation rental in Winchester like?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Winchester. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.

Recent reviews of Winchester properties
Expedia verified reviews

Get away from it all! Restored 1800 log cabin modern amenities 40 private acres

Get away from it all! Restored 1800 log cabin modern amenities 40 private acres

5/5 Excellent
Lovely Place
"This is a wonderful property. Quiet, serene, spotless, welcoming."
A verified traveler stayed at Get away from it all! Restored 1800 log cabin modern amenities 40 private acres
Posted 2 days ago
Get away from it all! Restored 1800 log cabin modern amenities 40 private acres