Entire home

Trailside Retreat in breathtaking Western Loudoun

Photo gallery for Trailside Retreat in breathtaking Western Loudoun

Exterior
Living area
Living area
Living area
Interior

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 8

Popular amenities

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

Explore the area

Map
Hamilton, VA
  • Tally Ho Theatre
    ‪10 min drive‬
  • Morven Park
    ‪13 min drive‬
  • Stone Tower Winery
    ‪17 min drive‬
  • Washington, DC (IAD-Washington Dulles Intl.)
    ‪25 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Single Bunk Bed

Bedroom 4

1 King Bed

3 bathrooms

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Porch or lanai
Kitchen
Dining area

About this property

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 manager

Jill Fowler
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings and birthday parties
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Pets

Pets allowed: dogs (limit 2 total)
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Smoking

Smoking is not permitted
throw bagged trash in outside trash can clean and put your dishes away take all food with you

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
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

About the area

Hamilton

Located in Hamilton, this holiday home is in a rural area. The area's natural beauty can be seen at Audubon Naturalist Society Rust Nature Sanctuary and Veterans Park at Bulls Bluff, while Tally Ho Theatre and Earth and Fire Gallery are cultural highlights. Purcellville Skating Rink and Museum of Hounds and Hunting are also worth visiting.
Map
Hamilton, VA

What's nearby

  • The Barns at Hamilton Station Vineyards - 2 min drive - 1.8 km
  • Tally Ho Theatre - 10 min drive - 9.9 km
  • Leesburg Corner Premium Outlets - 12 min drive - 15.2 km
  • Morven Park - 13 min drive - 11.6 km
  • Stone Tower Winery - 17 min drive - 15.5 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
  • ‪McDonald's - ‬6 min drive
  • ‪The Purcellville Pub - ‬6 min drive
  • ‪Monk's BBQ - ‬8 min drive

Frequently asked questions

Is Trailside Retreat in breathtaking Western Loudoun pet-friendly?

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

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. W&OD Trail and Washington & Old Dominion Trail Regional Park are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 41 out of 44 reviews
Rating 8 - Good. 2 out of 44 reviews
Rating 6 - Okay. 1 out of 44 reviews
Rating 4 - Poor. 0 out of 44 reviews
Rating 2 - Terrible. 0 out of 44 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

8/10 Good

Jeff P.

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

Very Comfortable Home

Convenient location and well kept home. There is no carpeting in the house, so if you have young ones, it will be noisy.
Stayed 2 nights in Dec 2024

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

Robert R.

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

50th Anniversary celebration

This property was perfect. We were able to host an outdoor picnic for family. Lot's of room for the kids to run and play. We were able to set up everything under the carport. Really enjoyed walking on the bike trail in the mornings.
Stayed 5 nights in Nov 2024

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

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

Jill S.

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

Short Getaway for Teen Son's Fall Break

The property is one of the best VRBO rentals that we have stayed in. I felt like it was clean and tidy in comparison to other ones. My only complaint would be trail access. We wanted to walk the dogs on the trail, but there were no directions on how to access it. The owner responded quickly to my question, but I shouldn't have had to ask. We had to walk down the road a few houses and use someone's driveway. The trail was nice! (We drove into DC two days and needed to exercise our dogs from sitting in cages for 6 hours.) Also, the exterior picture made it look like it was way out in the open. However, there is a house next door that is fairly close and the trail is basically in the backyard. We enjoyed the fresh eggs! There was plenty of inside space and lots of toiletries. We didn't need to bring or buy any soap, paper products, shampoo, etc! As another reviewer stated, the temp between the floors is noticeable. We would definitely stay again.
Stayed 3 nights in Oct 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

Mary W.

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

Girls wine/birthday weekend

Wonderful, relaxing, quiet location, house was convenient and clean. Would like to have had firewood upon arrival and the deck cleared off from leaf debris. Jill was responsive to our questions. It would’ve been helpful if directions were left on how to enter the trail behind the house. Would highly recommend this property for a great getaway!😀🍷
Stayed 3 nights in Oct 2024

10/10 Excellent

Marion K.

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

Perfect for the Solheim Cup!

Four of us enjoyed our stay, using Trailside Retreat as our base while attending the Solheim. It was perfect for our purposes. The kitchen is large and well-appointed. Communication with Jill is timely. Highly recommend! Our only wish would be for separate controls for the heating/cooling unit for upstairs and downstairs. (A mini-split would take of it). The fresh eggs were a nice touch!
Stayed 4 nights in Sep 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

6/10 Okay

Regina S.

Liked: Check-in
Disliked: Communication

Irene Road

The beds were comfortable. The water pressure in the showers sucked, very little pressure and took longer to rinse my hair. There were spiders and webs in the house. Dust on tables. Smell of carpet freshener wasn’t very nice. Pictures were deceiving. The bathroom in the master upstairs was tiny without counter space to leave your belongings. The cleaners didn’t even sweep off the deck we did and previous tenants left food on the outdoor grill and cheese on the trash can. The outdoor furniture hadn’t been wiped off, there were cob webs all over it I expected more for the money.
Stayed 3 nights in Aug 2024

10/10 Excellent

Diane P.

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

Family celebration

Stayed 3 nights in Mar 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

10/10 Excellent

Beth Ann H.

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

Convenient location to attend a Leesburg wedding!

The best VRBO we've stayed in by far. Topping the list of what we appreciated was cleanliness. You get that fresh-cleaned smell the moment you walk in the door! So well stocked. I packed extra TP, paper towels, etc that I never even got out. Kitchen is particularly well stocked. Very tastefully decorated. Lower-level bedroom, full bath and living area make it nice to give some folks their own space. Short, easy drive to Leesburg & Purcellville. And Jill is an incredibly kind and attentive host. She went above and beyond to accommodate us and make us feel comfortable. Thank you Jill!
Stayed 3 nights in Jul 2024

10/10 Excellent

Tina D.

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

Sibling ebike trip

The property presented as posted on VRBO. We were able to utilize all aspects of the house and grounds dispite the heat.
Stayed 8 nights in Jun 2024

10/10 Excellent

Richard F.

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

Nice

Everything was nice and clean. Had what we needed for a long weekend. Location is wonderful close to everything.
Stayed 4 nights in Jun 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

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

SavedbyGrace

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

Peaceful

The property is as described on the website. The outside and inside are both well maintained. The decor is very nice and the furniture including the beds are comfortable. We had a group of family staying for our son’s wedding. The downstairs has its own bedroom, bathroom and living room. Great to have the separation at times. We wish we could have had time to enjoy the deck and fire pit. We would definitely stay again.
Stayed 4 nights in May 2024

10/10 Excellent

Rick H.

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

Perfect spot for the family events in Loudoun County

We had 6 adults and 1 baby stay here for a family wedding that was close by at one of the "barn" venues. The place is as advertised. Very clean and updated. The host was very gracious and communication was outstanding. Now that we know about it, we will book again for the next family event in Virginia. Highly recommend.
Stayed 3 nights in May 2024

About the host

Hosted by Jill Fowler

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests