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Entire apartment

Pretty Little Apt by the Train II

2.0 star property
Apartment in Winchester

Photo gallery for Pretty Little Apt by the Train II

Interior - Pretty Little Apt by the Train II (Winchester)
TV - Pretty Little Apt by the Train II (Winchester)
Private kitchen - Pretty Little Apt by the Train II (Winchester)
Interior - Pretty Little Apt by the Train II (Winchester)
TV - Pretty Little Apt by the Train II (Winchester)
Welcome to this charming downtown apartment, full of light and personality. Enjoy your morning coffee on the porch swing, listening for the train in the distance. The main bedroom has a queen-sized bed and large closet, plus a turntable with vinyl records to set the mood.

Reviews

9.8 out of 10
Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 2

Popular amenities

  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

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 .

Property amenities

Internet

  • Available in the apartment: WiFi

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Porch/lanai

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

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Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age - 21

Check-out

Check-out before 12:00 PM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

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

  • ‪Piccadilly's Public House & Restaurant - ‬1 min walk
  • ‪Hideaway Café - ‬4 min walk
  • ‪Water Street Kitchen - ‬6 min walk
  • ‪Roma Old Town Wood-Fired Pizzeria - ‬5 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.

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.

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Pretty Little Apt by the Train II Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens 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

Cleanliness

9.8

Location

Reviews

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