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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 123 Apartments in Winchester with updated reviews, rates, and availability.

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
Terrace/patio

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

9.6 out of 10, Exceptional, (13)
"Gorgeous Fall foliage @ a quaint cabin close to everything "
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
Hidden Gem Charming 2-bedroom apartment in delightful Lexington
Interior

Hidden Gem Charming 2-bedroom apartment in delightful Lexington

2.0 star property
Hidden Gem Charming 2-bedroom apartment in delightful Lexington
Lexington Apt. with parking & private entrance Preview listing
Exterior

Lexington Apt. with parking & private entrance Preview listing

10.0 out of 10, Exceptional, (123)
"Clean, well supplied and convenient location. Well satisfied. No problems at all."
The price is AED 268
AED 545 total
includes taxes & fees
31 Mar - 1 Apr
Lexington Apt. with parking & private entrance Preview listing
Chic Main Street Retreat < 7 Mi to KY Horse Park!
Coffee/tea maker

Chic Main Street Retreat < 7 Mi to KY Horse Park!

10.0 out of 10, Exceptional, (55)
"Beautiful, spacious, well equipped loft on a charming small town downtown."
Chic Main Street Retreat < 7 Mi to KY Horse Park!
This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Exterior

This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

9.0 out of 10, Wonderful, (18)
"Check in was easy. Small but perfect for me and my S/O. The bed broke while sleeping Night 2. Messaged the P.M. Took a little while but she finally messaged back. They sent someone out and it was fixed when we got back from dinner. Overall, 4.5/5 would stay again. Area is quiet residential and had wonderful neighbors. 5 blocks from everything you need. "
The price is AED 311
AED 783 total
includes taxes & fees
27 Mar - 28 Mar
This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.
Quaint Apartment in Historic Georgetown!
Fridge, microwave, stovetop, coffee/tea maker

Quaint Apartment in Historic Georgetown!

9.8 out of 10, Exceptional, (41)
"Property was such a great place to use as a home base for our stay "
Quaint Apartment in Historic Georgetown!
Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75
Fridge, microwave, oven, stovetop

Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75

2.0 star property
9.6 out of 10, Exceptional, (5)
"Our children had an adventure planned with their cousins, so we came down for the day and needed a place to stay and this was perfect. Good beds for everyone and an easy check-in. The host reached out to make sure we had everything we needed and everything was perfect."
The price is AED 334
AED 858 total
includes taxes & fees
27 Mar - 28 Mar
Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75
Luxury on Main / South
Fridge, microwave, oven, stovetop

Luxury on Main / South

10.0 out of 10, Exceptional, (36)
"Always a experience. "
The price is AED 349
AED 668 total
includes taxes & fees
30 Mar - 31 Mar
Luxury on Main / South
Treetops Solar Sanctuary
Property grounds

Treetops Solar Sanctuary

10.0 out of 10, Exceptional, (70)
"It makes no sense to stay in a hotel when this unit is available. Perfect for a single or couple. Close to Chevy Chase and downtown. Very clean and has all you need for a comfortable stay. Dru is a first class host. Very attentive. "
The price is AED 235
AED 611 total
includes taxes & fees
31 Mar - 1 Apr
Treetops Solar Sanctuary
PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT! New building Urban Studio
Fridge, microwave, oven, stovetop

PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT! New building Urban Studio

9.4 out of 10, Exceptional, (64)
"Host was very helpful and accom9dating. Great coffee shop and breackfast/brunch right across the street. I highly reccomend."
PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT! New building Urban Studio
The Tiny Feather Summ
Aerial view

The Tiny Feather Summ

9.2 out of 10, Wonderful, (10)
"The Tiny Feather is so cute! We enjoyed the comfy beds and outdoor living space. Our daughter didn’t want to leave at the end of the weekend!"
The Tiny Feather Summ
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
Property grounds

Newly Renovated 2BR Apartment w/ Free Parking in Downtown

10.0 out of 10, Exceptional, (31)
"We have stayed at this property twice and it's really great. Looks just like the photos, clean and well appointed. We were located close enough to walk to downtown and restaurants. Great value. Eee would stay here over and over"
Newly Renovated 2BR Apartment w/ Free Parking in Downtown
Stylish Studio Apartment in Downtown Lexington
Iron/ironing board, WiFi

Stylish Studio Apartment in Downtown Lexington

2.0 out of 10, (1)
"The first night we stayed here, we got locked out of the house because the batteries for the automatic lock had died. We called the maintenance guy, but he was not able to get in as there was not a spare key where the owner said it was. The owner stopped answering his phone and essentially left us stranded. We ended up having to crawl through a window to get in. Additionally, the water pressure in the shower is no more than a trickle."
Stylish Studio Apartment in Downtown Lexington
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Property grounds

Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

9.8 out of 10, Exceptional, (89)
"Good place. Beds a little hard for older people"
The price is AED 441
AED 841 total
includes taxes & fees
30 Mar - 31 Mar
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment
Private kitchen

The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment

7.8 out of 10, Good, (6)
"Beautiful remodeled older house into apartments. I love this place. Second time I stayed there!! Only issue is that it's hard to work the dead bolt on entry door. Great hosts. Great accomodations!"
The Colonels Apartment is a freshly renovated 3bedroom 1bath downtown Richmond apartment
Springside Equine Getaway
Smart TV, books

Springside Equine Getaway

10.0 out of 10, Exceptional, (8)
"We enjoyed staying spring side for the holiday. Baked four pies in the fully stocked kitchen to share at our family thanksgiving down the road. Will definitely be back when we’re next in town. "
The price is AED 496
AED 830 total
includes taxes & fees
7 Apr - 8 Apr
Springside Equine Getaway
Location location location-#15015318-1
Exterior

Location location location-#15015318-1

10.0 out of 10, Exceptional, (26)
"The property was warm and convenient to everything around town . It was super clean, warm, and spacious for us. It had all of the amenities that we needed. The beds were very comfortable. "
Location location location-#15015318-1
Comfy Upstairs 2 bed/1 bath near EKU in Richmond
Fridge, microwave, oven, stovetop

Comfy Upstairs 2 bed/1 bath near EKU in Richmond

10.0 out of 10, Exceptional, (27)
"I came to visit my brother and it was perfect for a quick stay to spend time with him while getting to see EKU. Very clean and accurate listing, highly reccomend!"
The price is AED 312
AED 526 total
includes taxes & fees
27 Mar - 28 Mar
Comfy Upstairs 2 bed/1 bath near EKU in Richmond
Luxury On Main / East
Private kitchen

Luxury On Main / East

10.0 out of 10, Exceptional, (1)
"I truly enjoyed my stay in this beautiful apartment. "
The price is AED 349
AED 668 total
includes taxes & fees
30 Mar - 31 Mar
Luxury On Main / East
Peaceful Location in walking distance to the University & Hospitals
Microwave, oven, stovetop, coffee/tea maker

Peaceful Location in walking distance to the University & Hospitals

Peaceful Location in walking distance to the University & Hospitals
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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Other property types in Winchester

Natural Bridge State Resort Park
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1510)
"Staff was very nice! The view was amazing "
The price is AED 426
AED 470 total
includes taxes & fees
8 Apr - 9 Apr
Natural Bridge State Resort Park
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
Exterior

Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (63)
"The cabin was great! A perfect cabin to enjoy a peaceful weekend. We loved it! The only bad thing was you Definitely need a 4X4! To get up the driveway. "
The price is AED 378
AED 784 total
includes taxes & fees
30 Mar - 31 Mar
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
Terrace/patio

Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!

9.2 out of 10, Wonderful, (75)
"They helped us out ASAP before we drove out due to inclimate weather conditions. Offered us multiple other safe locations or cancellation/rescheduling and communicated consistently.Our cabin was clean as a whistle with every little thing we may have forgotten accomodated. It's super cute,comfortable and perfect for a getaway in the trees!!"
The price is AED 565
AED 970 total
includes taxes & fees
14 Apr - 15 Apr
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
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.

Frequently asked questions

What's it like to stay at an apartment in Winchester?
There are plenty of places to stay with in the larger Lexington area, with 944 lodging choices including 169 apartments. Any visit to a new destination can be a culinary trip so why not visit the local restaurants?
How do you know if an apartment is the best choice for you?
An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, but also for families who want the conveniences of home.
What's a favorite apartment for a stay in Winchester?
Here are some of the more popular apartments in the area: 2nd Story Historic Downtown 2BR with Modern Amenities: Includes free WiFi and sofa beds. Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!: Located 30.3 mi/48.8 km away in Stanton. Amenities include private patios. Access to a hot tub is available on site. Private One Bedroom Apartment in Downtown Lexington near Rupp Arena: It’s situated in Lexington, 18.3 mi/29.4 km away. Includes free WiFi, private patios, and fireplaces. This apartment is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.: 16.5 mi/26.6 km away in Lexington. Free WiFi and Smart TVs are included. Lexington Apt. with parking & private entrance Preview listing: It’s located in Lexington, 21.1 mi/34 km from Winchester. Includes free WiFi and private patios.
What can I expect from the weather in Winchester?
Weather is only one factor, but it can really affect your travel plans, especially if you are planning a longer stay in Winchester. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.
What should I see and do in Winchester?
Winchester is known for its restaurants. Lykins Park and College Park are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Other places in town to visit include Southwind Golf Course and Cassell Creek Golf Course.
What's the best way to get to and around Winchester?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Blue Grass Airport (LEX), which is located 23 mi (37.1 km) from the heart of the city. If you’d like to venture out around the area, you may want a rental car for your journey.