Skip to main content
Entire home·Private host

Trailside Retreat in breathtaking Western Loudoun

Holiday home in Hamilton with kitchen

Photo gallery for Trailside Retreat in breathtaking Western Loudoun

Dining
Outdoor dining
Interior
Smart TV
Exterior
Step into this spacious 4-bedroom haven in Loudoun County's picturesque countryside, overlooking the changing seasons of a historic farm. Unwind under the covered porch or take a stroll on the W&OD Trail just behind the house, with bikes available on-site. Start your day with a luxurious coffee and tea bar, then explore local wineries like The Barns of Hamilton Station Vineyard or indulge in fresh produce at Paige’s Pit Stop Farmer’s Market.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 8

Popular amenities

  • Dryer
  • Washer
  • Barbecue grill
  • Kitchen
  • Pet-friendly
  • Parking available

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Trailside Retreat in breathtaking Western Loudoun

This warm and inviting house is located in the gorgeous, pastoral countryside of Loudoun County. It is situated across from one of the longest running farms of Hamilton. Our recently furnished and decorated spacious 4 bedroom abode overlooks breathtaking views of this seasonal changing farm . You will enjoy the expanse of the night sky from the large front yard or comfortably seated under the covered porch. A luxurious coffee and tea bar await you in the morning hours. Then take a stroll or bike ride on the W&OD Trail situated just behind the house. It stretches for miles taking you all the way to Washington DC if you need a hard workout. You will find bikes located in the shed on the property.
Just up the road you will find The Barns of Hamilton Station Vineyard, one of Loudoun County’s finest wineries, Paige’s Pit Stop Farmer’s Market, and The Mercantile offering local produce, groceries, flowers and a full coffee cafe. Minutes from the Appalachian Trail, Great Country Farms, Bear’s Den overlook, and Bear Chase Brewery. You won’t be disappointed visiting our wonderful area. Delicious restaurants, hiking trails, specialty shops, rivers, wineries, breweries and farms await you to be enjoyed.
* Our location is 10 minutes from Leesburg and 10 minutes from Purcellville. The house is stocked with trash bags, dish detergent, dishwasher detergent, laundry soap, shampoo, conditioner, body wash, bath epsom salt, all linens, towels, coffee, sugar, tea, honey, spices, toilet paper, paper towels, hand soap, and when available, farm fresh eggs!
*I am happy to have a basket with a bottle of local wine, cheese, salsa, chips, and chocolates waiting to welcome your arrival. All from locals enjoying the creation of their expertise. This would be an additional charge of $89. Just let me know you would like this service.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Porch/lanai

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location

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 (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

Similar properties

Dining
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
  • Washer
  • Dryer
  • Pet-friendly
  • Free WiFi
10.0 out of 10, Exceptional, 33 reviews
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 21

Check-out

Check-out before 11:00 AM

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

throw bagged trash in outside trash can clean and put your dishes away take all food with you

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets

Children and extra beds

Children are welcome

Events

Events allowed: family gatherings and birthday parties

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 20
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 indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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
Hamilton, VA

What's nearby

  • Hunters Run Wine Tasting Barn - 4 min drive - 4.9 km
  • Morven Park - 5 min drive - 6.7 km
  • Leesburg Corner Premium Outlets - 11 min drive - 17.4 km
  • Stone Tower Winery - 16 min drive - 19.7 km
  • Tysons Corner Center - 37 min drive - 64.1 km

Getting around

  • Harpers Ferry Station - 30 min drive
  • Washington Dulles International Airport (IAD) - 25 min drive

Restaurants

  • ‪Chick-fil-A - ‬5 min drive
  • ‪Starbucks - ‬5 min drive
  • ‪Dunkin' - ‬5 min drive
  • ‪Coach's Corner Grill - ‬5 min drive
  • ‪McDonald's - ‬6 min drive

Frequently asked questions

Is Trailside Retreat in breathtaking Western Loudoun pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Trailside Retreat in breathtaking Western Loudoun ?

On-site parking is available at the property.

What time is check-in at Trailside Retreat in breathtaking Western Loudoun ?

Check-in begins at 4:00 PM.

What time is check-out at Trailside Retreat in breathtaking Western Loudoun ?

Checkout is at 11:00 AM.

Where is Trailside Retreat in breathtaking Western Loudoun located?

Situated in a rural location, this holiday home is steps from Catoctin Valley and within 3 mi (5 km) of The Barns at Hamilton Station Vineyards and Hunters Run Wine Tasting Barn. Patrick Henry College and Purcellville Plaza are also within 6 miles (10 km).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Trailside Retreat in breathtaking Western Loudoun Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 51 out of 54 reviews
Rating 8 - Good. 2 out of 54 reviews
Rating 6 - Okay. 1 out of 54 reviews
Rating 4 - Poor. 0 out of 54 reviews
Rating 2 - Terrible. 0 out of 54 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Nathan V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend Stay

Great location and very clean and fun
Stayed 2 nights in May 2025

10/10 Excellent

John D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Destination Wedding Week

6 adults and one child stayed for 5 days for a extended vacation during a destination wedding. Could add one more child in bunkbed. Accommodations were great and as advertised. Location immediately off of Hwy 7 was ideal. 3 bathrooms on wedding day made a potentially hectic morning a breeze.
Stayed 5 nights in Jun 2025

10/10 Excellent

JENNIFER L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, very clean and very well maintained. We were here for a softball tournament for 4 days of play and it was so nice to come back to a quiet home in the country to relax before the next day of full play. The washer and dryer and 3 bathrooms was worth its weight in gold for us. Grilling out and having time to relax in peace was priceless. We will definitely be back next year and will be booking this fantastic home again.
Stayed 4 nights in Jul 2025

8/10 Good

Emily M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay in Hamilton

It was an excellent place to stay close to Leesburg and Purcellville, right off Route 7. The house was quiet and had a great setup for a family of elementary/middle school-aged kids. I would stay there again and recommend it to other families!
Stayed 3 nights in Jan 2025

10/10 Excellent

Kathleen O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful home perfectly situated outside Leesburg

The houses wonderfully decorated and super clean. Has many amenities. It’s very convenient if you’re visiting Leesburg. Lots of awesome restaurants in the general vicinity and interesting historical sites.
Stayed 4 nights in Mar 2025

10/10 Excellent

Donna A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Harry potter trip

Wonderful place!!!
Stayed 2 nights in Nov 2024

10/10 Excellent

jodie s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hamilton Stay

Beautiful home. Nice location Enjoyed our stay very much
Stayed 2 nights in Nov 2024

10/10 Excellent

Catherine M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Terrific place

Really terrific place. Plenty of room for everyone a large, beautiful yard where we could play with our dog very peaceful and quiet. The whole family really enjoyed the stay.
Stayed 3 nights in Jun 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect for our girl's gathering. Aside from the occasional voices coming from walkers on the bike trail (not bothersome at all) it was very quiet and serene. There was plenty of space to spread out even though we congregated mostly upstairs near the kitchen. We really enjoyed the space outside under the car port. Close access to Downtown Leesburg and Purcellville. Kitchen was stocked enough for our needs, as well as items for the bathrooms. Zero issues with the property which allowed us to enjoy our time together.
Stayed 4 nights in Jul 2025

10/10 Excellent

Jennifer K., Manassas, VA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Nice, clean and fantastic spot to enjoy the walking path and proximity to purcellville and leesburg both
Stayed 2 nights in Nov 2023

10/10 Excellent

Mary-Clare M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Gathering

We used this home for family overflow for a family get together and it was wonderful!
Stayed 3 nights in Oct 2024

10/10 Excellent

Samantha H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family stay

Great place for my family for our weekend visiting friends. Close to them and to wineries and breweries. Clean and plenty of towels and sheets.
Stayed 3 nights in Mar 2024

10/10 Excellent

Bill P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Winery Tour Location

Four of us stayed for a long weekend of wineries and breweries. The house could not have been in a better location an a perfect fit for two couples.
Stayed 4 nights in Aug 2024

10/10 Excellent

Neil W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice place in the country

Large house, good for a big group. Well equipped. Accommodated our need for an early check-in.
Stayed 3 nights in Jan 2025

10/10 Excellent

Jan c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful retreat in Virginia

Everything was wonderful. Very clean, comfortable and beautiful
Stayed 4 nights in May 2024

10/10 Excellent

Sophia G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent VRBO in Loudoun County

We had an excellent stay at Jill’s VRBO! The home was spacious and clean, perfect for a relaxing weekend away. The location also is ideal for going to wineries near Leesburg and Middleburg. And Jill was a very attentive host— she made sure that someone was there to remove the snow from the driveway and responded to any messages we sent promptly.
Stayed 3 nights in Jan 2025

10/10 Excellent

Gerlyn Rose L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Home away from home

It was a wonderful and beautiful home! We had a simple wedding reception under the garage. Thank you jill for accepting us into your home. The guys wanted to mow the lawn just for fun lol. This is definitely a lovely place to rent for a short or long stay. Everything 10 out of 10!
Stayed 6 nights in Apr 2025

10/10 Excellent

Sally W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house

We had such a lovely time in Virginia. This property was so clean and well appointed. We also enjoyed the location right next to the W&OD trail.
Stayed 3 nights in May 2024

10/10 Excellent

Heather L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice get away

Perfect location to the trail for hiking and biking. Close to vineyards. House is very comfortable. Great stay.
Stayed 2 nights in Mar 2024

10/10 Excellent

Elizabeth J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved our stay

House was spotless and well-appointed. Minutes away from shops and restaurants in Purcellville and Leesburg. Thoughtful host provided everything we needed for our girls getaway weekend. Would stay here again!
Stayed 2 nights in Mar 2024

10/10 Excellent

Renee C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cousin’s trip

Met cousins for a “girls weekend” and had a wonderful time. The property and our stay were great! It was comfortable and just perfect for our group to relax and catch up.
Stayed 2 nights in Jan 2024

10/10 Excellent

Lisa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Experience

We had a full family 4 day retreat and Jill’s place was perfect. Lots of room, beds were so comfy and contained all the kitchen and bathroom supplies we needed. Everything was clean - they even had some toys for the kids. Great location…convenient to all activities, restaurants and hiking trails. We would definitely book again. 5 stars!
Stayed 4 nights in Jan 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful and relaxing

This property was beautiful. The house has been updated top to bottom with beautiful finishes. Plenty of room to gather and spread out. Highly recommend.
Stayed 2 nights in Nov 2024

10/10 Excellent

Diane A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

This house is located near wonderful walking paths and a short drive to Leesburg. It worked well for our group of 6 adults. We appreciated the fact that our bedrooms had access to individual bathrooms, each with lots of towels. Additionally, there is plenty of parking.
Stayed 2 nights in Oct 2024

10/10 Excellent

Tammy C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Reunion escape home

This was the perfect home to get away for quiet time from our family reunion! Me, my sister, and her family, stayed with our 2 dogs and it was perfect. Great location and picturesque yard that made for much needed relaxing. The house was very clean and well furnished!
Stayed 3 nights in Jul 2024