Pretty Little Apt by the Train II

Photo gallery for Pretty Little Apt by the Train II

A kitchen with a white countertop, a sink, a coffee maker, and a window with a view of trees.
A living room with a sofa, two side tables with lamps, a coffee table, a plant, and a window with curtains.
A compact kitchen with a refrigerator, stove, microwave, and a shelf with various kitchen items.
A porch with a white bench, two metal chairs, a small round table, and a potted plant.
A dining area with a wooden table and chairs, a ceiling fan, and a view into the kitchen.

Reviews

9.6 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Shenandoah Valley Discovery Museum

Popular amenities

  • Free Wi-Fi in public areas
  • Pet-friendly
  • Kitchen
  • Air-conditioning
  • Non-smoking

Explore the area

View map
Winchester, VA
  • Place, Handley Regional Library
    ‪5 min walk‬
  • Place, Bright Box Theater
    ‪6 min walk‬
  • Place, Shenandoah Valley Discovery Museum
    ‪9 min walk‬
  • 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

Spaces

Porch or lanai

Add dates for prices

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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. Nalls Farm Market and Frederick County Fairgrounds are also worth visiting.
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Map
Winchester, VA

What's nearby

  • Handley Regional Library - 5 min walk - 0.5 km
  • Bright Box Theater - 6 min walk - 0.6 km
  • Old Court House Civil War Museum - 6 min walk - 0.6 km
  • Shenandoah Valley Discovery Museum - 9 min walk - 0.8 km
  • Patsy Cline Historic House - 12 min walk - 1.1 km

Getting around

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

Restaurants

  • ‪Hideaway Café - ‬4 min walk
  • ‪50/50 Taphouse - ‬10 min walk
  • ‪Violino Ristorante Italiano - ‬3 min walk
  • ‪Water Street Kitchen - ‬6 min walk
  • ‪Pizzoco Pizza Parlor - ‬8 min walk

Frequently asked questions

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

Yes, this property allows cats and dogs (limit 1 total).

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

9.6

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. 8 out of 10 reviews
Rating 8 - Good. 2 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

9.4/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect for us. We wanted a comfy and relaxing place to stay during a long road trip. The house is cute and Michele was awesome to work with.
Stayed 1 night in Sep 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location for walking around Old Town Winchester!
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was decorated very cute and the bed was comfortable. Very close to shops and restaurants.We had to drive around the block and get out to find the location because you park and enter through the back door.It’s very close to the train stain but was only interrupted by an early morning train once.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Convenient and bice

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

8/10 Good

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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
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