Is this Old Town Winchester apartment pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Old Town Winchester apartment have a swimming pool?

No, this Old Town Winchester apartment does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

Is Old Town Winchester apartment a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this apartment 2 stars or guests have recommended them suitable for families. As reported by the owner or manager, the apartment has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Old Town Winchester apartment wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Old Town Winchester apartment has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Old Town Winchester apartment?

Based on the information reported by the owner or manager, the Old Town Winchester apartment indicates 1 day stay policy at this apartment. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Old Town Winchester apartment?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Pretty Little Apt by the Train II | Apartment in Winchester

Q: How much does it cost per night to stay in Old Town Winchester apartment?

Best-rates for the Old Town Winchester apartment starts from $164 per night with includes Child Friendly, Internet, Air Conditioner, TV, Security/Safety, Bedding/Linens, Wellness Facilities, Fireplace/Heating, Laundry with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

9.8 (7 Reviews) | 1 Bedroom 1 Bathroom 2 Guests

Old Town Winchester Apartment | Pretty Little Apt by the Train II

1 Bedroom Apartment in Old Town Winchester, Winchester

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 .

Pretty Little Apt by the Train II is located in Old Town Winchester. Pretty Little Apt by the Train II provides accommodation, featuring Internet, Air Conditioner, TV, among other amenities. This Apartment features Internet, Air Conditioner, TV, to make your stay a comfortable one.

Pretty Little Apt by the Train II has 1 Bedroom , 1 Bathroom, and max occupancy of 2 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have rated it 2, and VRBO labeled it a top-rated Apartment because of the excellent services rendered by the owner or manager of this Apartment, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Apartment has a friendly neighborhood, and the Old Town Winchester has interesting places to visit. If you want to learn more about the Apartment in Old Town Winchester, such as places to visit and things to do nearby, you can check below to learn more.

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

Air Conditioner

Security/Safety

Bedding/Linens

Wellness Facilities

Fireplace/Heating

Child Friendly

Internet

Laundry

Facility Overview

Air Conditioner

Heating

Air conditioning

Bathrooms

Hair dryer

Towels provided

1 bathroom

Toilet paper

Soap

Bedroom

Bed sheets provided

1 bedroom

Pet Friendly

No pets allowed

Accessibility

Smoke-free property

Entertainment

TV with cable/satellite service

General

English

Guest Services

Iron/ironing board

Internet

Free WiFi

Outdoors

Porch or lanai

Security/Safety

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

Child Policy

Children are welcome.

Event Policy

No events allowed

Pet Policy

Pets not allowed

Smoking Policy

Smoking is not permitted

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 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 onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

Sarah B.

Sep 29, 2025 04:34:29 AM

Review Score: 10

Summary: 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.

See All Reviews