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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
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!
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, 49 reviews

Jaw Dropping Getaway in the Heart of RRG!

ColleenRating, 5 stars3 weeks ago
This home is at the end of a private drive and is out on a peninsula overlooking beautiful scenery. The house was plenty big for our family of 13 and guests who visited. The decking around the entire house was lovely and the zip line right next to the property was fun to watch. The kids loved having their own spaces.
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 stars3 days 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
An exterior view of a modern patio area features stacked stone benches surrounding a fire pit. A black metal staircase leads to an upper level, framed by textured brick walls and lush greenery. Paved pathways extend through the outdoor space.
Apartment in Lexington
4.84 out of 5 average rating, 37 reviews

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

ToliverRating, 5 stars4 weeks ago
Great location. Easy parking. Nice layout of the apartment.
Guest favorite
Home in Lexington
4.97 out of 5 average rating, 106 reviews

Hot Tub | Great Location | Patio | Grill | Ping Po

LaineRating, 5 stars3 days ago
I had to rent for a crowd and this was a great place lots of accommodation and amenities
Top guest favorite
A wooden pergola is featured in a grassy yard, complemented by vibrant greenery and a well-maintained path of pavers. The expansive landscape extends in the background, showcasing an open view of the surrounding area.
Home in McKee
5 out of 5 average rating, 15 reviews

Roca Rental Home

PaulRating, 5 stars4 days 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 stars1 week ago
It's a peaceful, serene location. Shirlene is an absolutely amazing host. You'll love it!
Top guest favorite
A rustic cabin is nestled among tall trees, elevated on a ridge. The structure features a wrap-around porch with multiple entry points, surrounded by lush greenery. Clear skies and soft clouds create a serene backdrop, enhancing the cabin's retreat-like atmosphere.
Cabin in Pine Ridge
4.96 out of 5 average rating, 112 reviews

Cliffside Family Retreat w/ View

AnjaRating, 5 stars1 week ago
As a family of 4 we had an awesome stay! The cottage was clean, the beds were comfortable, the view was amazing and the whirlpool very relaxing after hiking. The outside fireplace was great for roasting marshmallows and having nice family evenings.

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

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