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Pretty Little Apt by the Train II

Apartment in Winchester

Photo gallery for Pretty Little Apt by the Train II

Interior
Interior
Point of interest
Living area
Private kitchen

Reviews

9.8 out of 10
Exceptional
1 bedroom1 bathroomSleeps 2

Popular amenities

  • Air conditioning
  • Free WiFi

Explore the area

View map
Winchester, VA
  • Place, Bright Box Theater
    ‪5 min walk‬
  • Place, Shenandoah Valley Discovery Museum
    ‪8 min walk‬
  • Place, Shenandoah University
    ‪3 min drive‬
  • Airport, Martinsburg, WV (MRB-Eastern West Virginia Regional)
    ‪22 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

About this property

Pretty Little Apt by the Train II

This little place is just plain charming.
Lots of light and personality.
Wonderful alternative to the typical hotel experience.
Fabulous for short term rental needs.
Come enjoy Downtown
Flat screen TV/ Record Player FREE PARKING/WIFI
Near Piccadillys Pub, the Walking Mall, our beautiful and historic library, Shenandoah Univ. -5 minute Winchester Med Center -5 min DC. -1.5 hr Skyline Drive -30 min
Free Parking too !

Reach out on social media if you need more. Michele Bouve Hoffman
The space
This vintage apartment above downtown shop is just plain charming. It is decorated with lots of light - and personality!
Enjoy your morning coffee on the porch swing and wait for the train to come by. The main bedroom has a queen sized bed and large closet. There is a turntable and some vinyl there for your enjoyment.
Many guests have been delighted with their stays and have said that the apt. is more spacious than it looks in pics .

Add dates for prices

Amenities

Free WiFi
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 12:00 PM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Quiet hours 10pm to 7 am

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property # 2677700vb

About the area

Winchester

Old Town Winchester, a neighbourhood in Winchester, is home to this apartment. Shenandoah Valley Discovery Museum and Rock Harbor Golf Course are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Apple Valley Square Shopping Center and Northside Station Shopping Center. Looking to enjoy an event or a game while in town? See what's going on at Summit Point Motorsports Park, or consider a night out at Barns of Rose Hill.
View more Apartments in WinchesterOpens in a new window
Map
Winchester, VA

What's nearby

  • Bright Box Theater - 5 min walk - 0.4 km
  • Handley Regional Library - 5 min walk - 0.5 km
  • Shenandoah Valley Discovery Museum - 8 min walk - 0.7 km
  • Museum of the Shenandoah Valley - 19 min walk - 1.7 km
  • Shenandoah University - 3 min drive - 2.8 km

Getting around

  • Martinsburg, WV (MRB-Eastern West Virginia Regional) - 29 min drive

Restaurants

  • ‪Hideaway Café - ‬4 min walk
  • ‪Piccadilly's Public House & Restaurant - ‬1 min walk
  • ‪Water Street Kitchen - ‬6 min walk
  • ‪Paladin Downtown - ‬2 min walk
  • ‪Espresso Bar & Cafe - ‬3 min walk

Frequently asked questions

Is Pretty Little Apt by the Train II pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Pretty Little Apt by the Train II?

As of 17 Dec 2025, prices found for a 1-night stay for 2 adults at Pretty Little Apt by the Train II on 11 Jan 2026 start from AU$294.42, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at Pretty Little Apt by the Train II?

Check-in begins at 3:00 PM.

What time is check-out at Pretty Little Apt by the Train II?

Checkout is at 12:00 PM.

Where is Pretty Little Apt by the Train II located?

Located in Old Town Winchester, this apartment building is within a 10-minute walk of Handley Regional Library, Old Court House Civil War Museum and Bright Box Theater. Mt Hebron Cemetery and Stonewall Jackson's Headquarters are also within 10 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 6 out of 7 reviews
Rating 8 - Good. 1 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Stephanie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again.
Stayed 3 nights in Oct 2025

10/10 Excellent

Sarah B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay and very comfortable apartment. And the host was great to work with. Just a few steps away from the Old Town pedestrian mall. Just know that the restaurant bar/grill across the street has outdoor live music until about 1am on Friday and Saturday nights.
Stayed 2 nights in Sep 2025

10/10 Excellent

Sheryl W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location, location!!We wanted to be by a local cider house…and we were. Walk to all kinds of food and shops. The outside is a little different, but we weren’t there for the outside. Inside is a cute little apartment. Loved our stay.
Across from a pub. This is the drive
Local cider
Local cider
Stayed 1 night in Sep 2025

10/10 Excellent

Barbara B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Convenient and bice

Great time. Love this city
Stayed 2 nights in Apr 2024

10/10 Excellent

Caroline S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a Great VRBO!

In old town! We were seconds away from everything! The apartment is filled with charm and is fully stocked. We were sad to leave! Thanks Michele for being so accessible!
Stayed 3 nights in Apr 2025

10/10 Excellent

Meg B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Place is just as described. Really cute. Large living room dining room and bedroom. Cute old fashioned kitchen. All tastefully decorated and well stocked. Starter coffee. A little strange configuration with bathroom as door to it from bedroom and dining area, but it really was not a problem for a couple. Right next to train but only had horn once in early eve and once in morning. Really easy walk to everywhere. Nice pub across street, and counter style diner just down street. Really great value. Parking easy.
Stayed 1 night in Oct 2025

8/10 Good

Christopher F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time. The location was great we were able to walk to many of the restaurants and historic homes we wanted to visit. Restaurant across the street has loud music Friday and Saturday nights, very busy area. The outside had a ton of trash right around the building that needs to be cleaned up. The apartment itself was very nice and we really enjoyed our stay. Visit Knead Bread right down the street - best place we went!
Stayed 2 nights in Oct 2025

About the host

Hosted by michele bouve hoffman

Host profile image

Languages:

English
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