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Pretty Little Apt by the Train II

Apartment perfectly located for exploring Old Town Winchester

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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 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.
A living room with a sofa, two side tables with lamps, a coffee table, a plant, and a window with curtains.

Reviews

9.6 out of 10
Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 2

Popular amenities

  • Pet friendly
  • Air conditioning

Explore the area

View in a 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)
    ‪25 min drive‬

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About the area

Winchester

Old Town Winchester stay.Within a 10-minute walk of this Old Town Winchester apartment, you'll find Handley Regional Library and Old Court House Civil War Museum. Bright Box Theater and Mt Hebron Cemetery are also within half a mile (1 km).
View more Apartments in WinchesterOpens in a new window

What's nearby

  • Handley Regional Library - 5 min walk - 0.5 km
  • Stonewall Jackson's Headquarters - 6 min walk - 0.6 km
  • Bright Box Theater - 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

  • McDonald's
  • ‪Oak Stone Craft Pizza and Bar - ‬19 min walk
  • ‪Hideaway Café - ‬4 min walk
  • ‪Arby's - ‬3 min drive
  • ‪Wendy's - ‬3 min drive

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 .

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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

  • Pet friendly
  • Welcoming cats and dogs only
  • One pet total

Suitability/Accessibility

  • Smoking not allowed

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)

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

Rules

Quiet hours 10pm to 7 am
Leave linens our cleaners strip them. Put used towels in the tub. Leave A/C’s on/turn off lights /lock door /return key where you got it. Thanks.
Check for all personal items and wash and put away any used dishes — pls leave apt how you found it :) thanks

Pets

  • Pets are welcome
  • Only dogs and cats are allowed
  • Maximum 1 pets
  • Service animals are exempt from fees

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
Onsite 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited.

Frequently asked questions

How close is Pretty Little Apt by the Train II to the airport?

This apartment is 19.8 mi (29-min drive) away from the Martinsburg, WV (MRB-Eastern West Virginia Regional) airport, the closest popular airport to the property.

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

As of Aug 14, 2026, prices found for a 1-night stay for 2 adults at Pretty Little Apt by the Train II on Aug 30, 2026 start from CA $181, excluding 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.

Does Pretty Little Apt by the Train II have an airport shuttle?

Airport shuttle services are not available at this apartment.

Does Pretty Little Apt by the Train II offer free breakfast?

This apartment does not offer free breakfast.

Is there a casino at Pretty Little Apt by the Train II?

No, there is no casino at this apartment.

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

Check-in begins at 3:00 PM.

Is there free parking at Pretty Little Apt by the Train II?

Free parking is not available at this apartment.

Does Pretty Little Apt by the Train II have a pool?

This apartment does not have a pool.

Does Pretty Little Apt by the Train II have a spa?

There are no spa services available at this apartment.

How close is Pretty Little Apt by the Train II to downtown Winchester?

This apartment is 0.2 mi away from Winchester.

Pretty Little Apt by the Train II Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 7 out of 9 reviews
Rating 8 - Good. 2 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

9.4/10

Cleanliness

Reviews

Verified review

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
Verified review

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
Verified review

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
Verified review

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
Verified review

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
Verified review

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
Verified review

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

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