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Pretty Little Apt by the Train II

Apartment in Winchester

Interior

Private kitchen

Outdoor dining

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.

Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 2

Popular amenities

Air conditioning
Free WiFi

includes taxes & fees

20 Oct - 21 Oct

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

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)

Similar properties

Exterior detail

Kitchen
Washer
Dryer
Pet-friendly

includes taxes & fees

4 Nov - 5 Nov

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

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 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

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 - 2.4 km
Apple Blossom Mall - 4 min drive - 4.2 km
Winchester Medical Center - 5 min drive - 3.9 km

Getting around

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

Restaurants

‪The Hideaway Cafe - ‬4 min walk
‪Piccadilly's Public House & Restaurant - ‬1 min walk
‪Paladin Downtown - ‬2 min walk
‪Water Street Kitchen - ‬6 min walk
‪Roma Old Town Wood-Fired Pizzeria - ‬5 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 19 Oct 2025, prices found for a 1-night stay for 2 adults at Pretty Little Apt by the Train II on 20 Oct 2025 start from NZ$376.01, 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.

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Pretty Little Apt by the Train II Reviews

10

Exceptional

10

Cleanliness

9.6

Location

10/10 Excellent

Barbara B.

8 May 2024

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

Sarah B.

28 Sept 2025

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.

25 Sept 2025

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

Caroline S.

27 Apr 2025

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