See all properties
Entire apartment

Pretty Little Apt by the Train II

2.0 star property
Apartment in Winchester

Choose dates to view prices

Photo gallery for Pretty Little Apt by the Train II

Interior
Outdoor dining
TV
Private kitchen
TV

Reviews

9.8 out of 10
Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 2

Popular amenities

  • Air conditioning
  • Free WiFi

Explore the area

View in a 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

Room options

You may also like

Ad
Snack bar

TRU By Hilton Winchester

Winchester
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
9.0 out of 10, Wonderful, 755 reviews
$79 nightly
The price is $86
Dec 1 - Dec 2
Total with taxes and fees
TRU By Hilton Winchester

About the neighborhood

Winchester

Located in Old Town Winchester within a 5-minute walk of Handley Regional Library, this apartment is within a 15-minute stroll of Old Court House Civil War Museum.
View more Apartments in WinchesterOpens in a new window

What's nearby

  • Bright Box Theater - 5 min walk - 0.3 miles
  • Handley Regional Library - 5 min walk - 0.3 miles
  • Shenandoah Valley Discovery Museum - 8 min walk - 0.5 miles
  • Museum of the Shenandoah Valley - 19 min walk - 1.1 miles
  • Shenandoah University - 3 min drive - 1.8 miles

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

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 .
The apartment is air-conditioned and features a separate bedroom. The apartment also includes an ironing board.

Similar properties

Interior
Rosamond nice downtown studio apt
  • Kitchen
  • Air conditioning
  • Parking available
  • Microwave
8.0 out of 10, Very Good, 2 reviews
$170 nightly
The price is $193
Nov 24 - Nov 25
Total with taxes and fees
Rosamond nice downtown studio apt

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

  • 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

Rules

Quiet hours 10pm to 7 am

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 3:00 PM
  • Check-out: 12:00 PM
  • Minimum check-in age: 21

We should mention

Details about charges, deposits, or other important information:

  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.

Frequently asked questions

What's there to see within easy reach of this apartment?

This apartment is situated in Old Town Winchester within a 10-minute walk of Bright Box Theater, Shenandoah Valley Discovery Museum, and Handley Regional Library. You'll also find Patsy Cline Historic House and Old Court House Civil War Museum less than a mile away.

Is parking available on site at this apartment?

No, this apartment doesn't offer parking.

Is this apartment associated with a casino?

No, this apartment is not connected to a casino.

Is there an indoor pool at this apartment?

No, there is no indoor pool at this apartment.

Does Pretty Little Apt by the Train II have a hot tub?

No, there isn't a spa tub at this apartment.

Does this apartment provide breakfast?

No, this apartment doesn't offer breakfast.

Does this apartment allow pets to stay free of charge?

No, pets aren't allowed at this apartment.

What is the closest airport to this apartment?

The closest major airport to this apartment is Martinsburg, WV (MRB-Eastern West Virginia Regional), which is 19.8 mi away (29 minutes by car).

Are there rooms with balconies that I can book at Pretty Little Apt by the Train II?

Yes, every apartment at Pretty Little Apt by the Train II comes with a porch.

Pretty Little Apt by the Train II Reviews

Reviews

9.8

Exceptional

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

Reviews

10/10 Excellent

Meg B., -

Liked: Cleanliness
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

10/10 Excellent

Stephanie L.

Liked: Cleanliness
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

8/10 Good

Christopher F.

Liked: Cleanliness
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

10/10 Excellent

Sarah B., Grapevine, TX

Liked: Cleanliness
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
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

Caroline S.

Liked: Cleanliness

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

Barbara B., Hampton Virginia

Liked: Cleanliness

Convenient and bice

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