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Places to stay in Winchester

Book unique places to stay, houses, and more on Airbnb

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Popular amenities for Winchester places to stay

Stay near Winchester's top sights

Engine House Pizza Pub8 locals recommend
Ale-8-One Bottling Co8 locals recommend
Bluegrass Heritage Museum7 locals recommend
Abettor Brewing Company6 locals recommend
Wildcat Willy's Distillery and Restaurant5 locals recommend
Legacy Grove Park4 locals recommend

Other great vacation rentals in Winchester

Guest favorite
A vibrant yellow kayak is positioned along a rocky riverbank, surrounded by dense greenery. The calm water reflects the sky and is flanked by towering cliffs in the background. Lush trees line the river, creating a serene landscape ideal for outdoor activities.
Bungalow in Frankfort
4.94 out of 5 average rating, 107 reviews

Not So Rustic Cabin Near Elkhorn Creek.

IsaacRating, 5 stars1 week ago
Great place and we would definitely stay again.
Guest favorite
Cabin in Beattyville
4.93 out of 5 average rating, 45 reviews

Marji's House

MadisonRating, 5 stars2 months ago
Jamie’s place was peaceful and exactly as described, making it the perfect getaway. On our first morning, we encountered a small issue, but Jamie was incredibly responsive and arrived at the house immediately to resolve it. His prompt assistance truly made our stay even more enjoyable. Overall, I had a fantastic experience and can’t wait to return! Thank you, Jamie, for being such a great host!
Top guest favorite
A serene waterway is framed by lush greenery and trees lining the banks. A small boat can be seen docked at a gentle slope leading down to the water, inviting exploration of the tranquil surroundings.
Home in Olive Hill
5 out of 5 average rating, 13 reviews

A Grayson Lake Getaway

BrianRating, 5 stars4 months ago
stayed here multiple times with a hunting lease of mine close to the area. I plan on spending multiple trips at this location again clean house and Stacey will help you with anything you need 100% recommend
Superhost
The Manor House is situated on a cliffside, surrounded by lush greenery and towering trees. The residence features a wrap-around deck, enhancing its panoramic views of the natural landscape. The circular driveway leads to the entrance, which is framed by expansive woodland.
Cabin in Leeco
4.84 out of 5 average rating, 50 reviews

Jaw Dropping Getaway in the Heart of RRG!

DeannaRating, 5 stars1 week ago
Stacy and Tristan were excellent hosts. They were always available for anything we needed. Communication and response were commendable. Friendly and accommodating. Cabin was super comfy!
Top guest favorite
Cabin in Stanton
4.98 out of 5 average rating, 102 reviews

Briar Patch Cabin-RRG | Fire Pit | Sunset | Wi-Fi

AmberRating, 5 stars1 week ago
This place was great. Had everything we needed. The beds were comfy. The back porch was so peaceful and relaxing. We would def stay here again.
Superhost
A modern kitchen features sleek cabinetry and stainless steel appliances. A spacious island with three bar stools provides seating. Natural light pours in from large windows, enhancing the warm wood flooring. Decorative items and plants complement the minimalist design.
Apartment in Lexington
4.84 out of 5 average rating, 37 reviews

Count Fleet @ 3Forty /2BR Apt/ Walk to Rupp Arena

ToliverRating, 5 stars1 month ago
Great location. Easy parking. Nice layout of the apartment.
Top guest favorite
A spacious front porch is visible, featuring white railings and a wooden floor. The view showcases a vast green lawn and gentle hills in the distance, with trees lining the horizon under a clear blue sky.
Home in McKee
5 out of 5 average rating, 15 reviews

Roca Rental Home

PaulRating, 5 stars1 week ago
Our stay was very nice. Great place, beautiful morning views, and sunsets. We felt right at home while we were there. Close to trails we hiked and nice to come back to and rest. Will check into staying here again if in the area.
Top guest favorite
A spacious bathroom features a large soaking tub centered in the room, complemented by two double sinks with adjacent mirrors. Light wood cabinetry and decorative floral wall art enhance the design. Neutral-toned flooring completes the relaxing atmosphere.
Home in McKee
4.93 out of 5 average rating, 128 reviews

Big Ridge Retreat, LLC

RebeccaRating, 5 stars2 weeks ago
It's a peaceful, serene location. Shirlene is an absolutely amazing host. You'll love it!

Quick stats about vacation rentals in Winchester

  • Total rentals

    20 properties

  • Nightly prices starting at

    $10 before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Winchester?

    Yes! Work meets play with ease at over 10 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winchester?

    Four-legged friends are welcome in Winchester. Choose from more than 10 vacation rentals for guests traveling with pets.

Destinations to explore

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  2. United States
  3. Kentucky
  4. Clark County
  5. Winchester