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Find Extended Stay Hotels in Winchester, KY

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Top Winchester Extended Stay Hotels | Reserve now, pay later

Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 star property
Winchester
8.4 out of 10, Very Good, (997)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
$81 nightly
The price is $89
Nov 23 - Nov 24
Total with taxes and fees
Best Western Winchester Hotel
Private kitchen
The Perch - NEW / Downtown!

The Perch - NEW / Downtown!

Winchester
10.0 out of 10, Exceptional, (2)
"The place was amazing! Very clean and comfortable. Great Italian restaurant down the street. Delicious dounuts around the corner.We went down to go into Lexington for Bourbon and wine tours. Would have liked to have a folder/ binder with information on what is in the area ( we did explore downtown) and also for information about checking out.We had 4 adults and could have used more towels (had 1 towel for each person) But we did make due.All in all would give this place 5 stars! We will be...
United States
Angela G.
$238 nightly
The price is $259
Nov 17 - Nov 18
Total with taxes and fees
The Perch - NEW / Downtown!
Dining
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.

Winchester
10.0 out of 10, Exceptional, (42)
"What a lovely property! We only got to stay one night, but would have enjoyed a longer stay. The house is super roomy, with lots of comfy places to sleep. We enjoyed the game room immensely as we were winding down from a long day on the road. Easy access to food and shopping. "
United States
Angela P.
$307 nightly
The price is $338
Dec 1 - Dec 2
Total with taxes and fees
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min.
Lobby
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3.0 star property
Lexington
8.6 out of 10, Excellent, (1211)
"Our stay was really good . Look forward to staying again!"
United States
Connie
$84 nightly
The price is $98
Nov 27 - Nov 28
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Property amenity
Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

2.5 star property
Lexington
9.2 out of 10, Wonderful, (365)
"Great place to stay!"
United States
Kristin
$85 nightly
The price is $98
Nov 17 - Nov 18
Total with taxes and fees
Everhome Suites Lexington - Horse Park
Exterior
Holiday Inn Express & Suites Richmond by IHG

Holiday Inn Express & Suites Richmond by IHG

2.5 star property
Richmond
9.0 out of 10, Wonderful, (902)
"The rooms were super clean, bed was comfy & the staff very friendly "
United States
Amy
$89 nightly
The price is $98
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express & Suites Richmond by IHG
View from room
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 star property
Slade
8.6 out of 10, Excellent, (1772)
"Beautiful autumn stay."
United States
Cheryl
$86 nightly
The price is $95
Dec 6 - Dec 7
Total with taxes and fees
Natural Bridge State Resort Park
House (1 Bedroom) | Interior
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2)
"This cabin was 100% the cleanest and nicest I’ve ever stayed in. Adorable, had everything needed for a comfortable stay. "
United States
Amy
$216 nightly
The price is $239
Nov 24 - Nov 25
Total with taxes and fees
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Terrace/patio
Home2 Suites by Hilton Georgetown

Home2 Suites by Hilton Georgetown

3.0 star property
Georgetown
9.6 out of 10, Exceptional, (1000)
"Excellent front desk personnel "
United States
Martha
$98 nightly
The price is $108
Nov 30 - Dec 1
Total with taxes and fees
Home2 Suites by Hilton Georgetown
Exterior
Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

3.0 star property
Lexington
9.6 out of 10, Exceptional, (462)
"Nice stay"
United States
george
$105 nightly
The price is $122
Nov 23 - Nov 24
Total with taxes and fees
Staybridge Suites Lexington S Medical Ctr Area by IHG
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.
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Frequently asked questions

What are the best extended stay hotels in Winchester?
Whether you're visiting Winchester for work or taking a well-deserved extended vacation, one of our 7 long-term rentals will be your perfect fit. These properties come with an average guest review rating of 8.9 and homely comforts including a kitchen, making them a favorite for long stays. Want amenities like a business center, a swimming pool and the ability to cook for yourself? Holiday Inn Express Lexington East - Winchester, an IHG Hotel ticks those boxes and more. Also consider Hampton Inn Winchester. Begin your day with a cup of coffee and a plate of freshly cooked eggs and then get exploring. This extended stay in Winchester comes with free internet services and a swimming pool.
Why book an extended stay hotel in Winchester through Expedia?
If you're searching for a long-term rental for your extended stay in Winchester, Expedia's got you covered. Filter your search results by price, location and rating to find your perfect long-term stay. Some of these great properties may even offer discounted weekly rates. Want to learn how to snag the best deals? Sign up to become an Expedia member for free and save tons of cash with special offers — plus you'll earn reward points on every booking. Our extended stay hotels in Winchester come with amenities like kitchens and dining areas, so even though you're miles away, you can still experience the feeling of home.
What can I expect from an extended stay hotel?
Featuring amenities such as kitchens, laundries and dining areas, extended stay hotels in Winchester can be a comfortable and wallet-friendly alternative to standard accommodations. Make home-cooked meals and wash your own clothes. Sometimes offering discounted weekly rates, extended stay hotels range from simple studios to luxurious and large options that'll fit everyone. They also offer many of the amenities you'd expect to find in a standard hotel, like housekeeping and 24/7 guest services. If you're searching for flexibility, privacy and a comfy retreat for a few weeks or longer, an extended stay hotel is just the ticket.

Top Winchester Hotel Reviews

Hyatt Place Lexington

Hyatt Place Lexington

10/10 Excellent
"Everything went swimmingly and the room is perfect and clean."
Jeffrey 1-night trip
Posted 6 days ago
Hyatt Place Lexington
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

10/10 Excellent
"The room was renovated, all new, very nice and clean. The staff was kind and helpful. Location of the hotel close to I-75 and easy to reach. I can really recommend this hotel."
Carla 1-night trip
Posted 7 days ago
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

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