Entire apartment

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. - Pretty Little Apt by the Train II (Winchester)
A compact kitchen with a refrigerator, stove, microwave, and a shelf with various kitchen items. - Pretty Little Apt by the Train II (Winchester)
A dining area with a wooden table and chairs, a ceiling fan, and a view into the kitchen. - Pretty Little Apt by the Train II (Winchester)
A porch with a white bench, two metal chairs, a small round table, and a potted plant. - Pretty Little Apt by the Train II (Winchester)
A living room with a sofa, two side tables with lamps, a coffee table, a plant, and a window with curtains. - Pretty Little Apt by the Train II (Winchester)
Pretty Little Apt by the Train II provides everything that you need. Guests can connect to free WiFi in public areas.

Reviews

9.6 out of 10
Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 2

Popular amenities

  • Pet-friendly
  • Air-conditioning

Add dates for prices

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 .

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

  • 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

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 allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs and cats only
1 total pets

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

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. Visit our Winchester travel guide
View more Apartments in Winchester
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.

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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. 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

Cleanliness

9.8

Location

Reviews

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