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Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views

Photo gallery for Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views

Exterior
Property grounds
Living area
Living area
Private kitchen

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms3 bathroomsSleeps 6232.3 sq m

Popular amenities

  • Breakfast included
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Greenwood, VA
  • Place, Pollak Vineyards
    ‪3 min drive‬
  • Place, Valley Road Vineyards
    ‪3 min drive‬
  • Place, Blue Ridge Parkway North Entrance
    ‪6 min drive‬
  • Airport, Charlottesville, VA (CHO-Charlottesville-Albemarle)
    ‪38 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 3

1 Single Bed

King Bedroom

1 King Bed

Primary Queen Bedroom

1 Queen Bed

3 bathrooms

En-Suite Bathroom

Toilet · Shower only

Full Bathroom

Toilet · Shower only

Hallway Bathroom

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

About this property

Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views

Welcome to Ramsay Estate Cottage, a gorgeous yellow Cape Cod in the Charlottesville countryside with sweeping views of the Blue Ridge Mountains. This charming 3-bedroom, 3-bathroom home is tastefully decorated in a casually elegant style and offers plenty of space for families or couples.

The cottage features a full kitchen, living and dining area, and a cozy family room perfect for reading or relaxing. Two bedrooms are located on the main level—the primary queen suite with a fireplace and ensuite bath, and a sunny king bedroom with a private hall bath—while the upstairs double twin bedroom and full bath create a quiet retreat for guests. Step out onto the screened porch to take in the fresh air or enjoy your morning coffee surrounded by gardens and mountain views.

Just outside, you are welcome to enjoy a private fire pit area (wood provided) and propane grill, and we invite you to explore the property's meticulous gardens, private vineyards, walking trails, animals, and creek. This historic property is home to five cows, thirty chickens, and eighteen acres of vineyards. We are just minutes from some of the top vineyards on the East Coast, including Chiswell Winery, Septenary, and King Family. Other local attractions include Greenwood Gourmet Grocery and Shenandoah National Park.

Ramsay Estate features additional accommodations and is a lovely retreat for larger groups and wedding parties- inquire with Guesthouses to book the entire estate for your special occasion. The property also has an on-site farm manager who is available to assist you during your stay. This is truly a special experience in the heart of Virginia's wine country!

Hosted by Guesthouses

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Greenwood

Located in Greenwood, this cottage is in a rural area and in the mountains. Crozet Tunnel and Swannanoa Palace are local landmarks, and the area's natural beauty can be seen at Shenandoah National Park and Rockfish Gap Entrance Shenandoah. Ready for a night out? Consider Pippin Hill Farm & Vineyards and Mount Fair Vineyard. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with ecotours, mountain biking and horse riding nearby.
View more Cottages in GreenwoodOpens in a new window
Map
Greenwood, VA

What's nearby

  • Pollak Vineyards - 3 min drive - 3.5 km
  • Valley Road Vineyards - 3 min drive - 6.3 km
  • Blue Ridge Parkway North Entrance - 6 min drive - 10.4 km
  • Rockfish Gap Entrance Shenandoah - 7 min drive - 11.4 km
  • Veritas Vineyard and Winery - 7 min drive - 12.3 km

Getting around

  • Charlottesville Station - 21 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 40 min drive

Restaurants

  • ‪King Family Vineyards - ‬9 min drive
  • ‪Starr Hill Brewery - ‬11 min drive
  • ‪Blue Mountain Brewery - ‬5 min drive
  • ‪The Yellow Mug - ‬9 min drive
  • ‪Praha Bohemian Bakery & Cafe - ‬9 min drive

Frequently asked questions

Is Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views?

As of 4 May 2026, prices found for a 1-night stay for 2 adults at Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views on 18 May 2026 start from NZ$1,140, 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.

How much is parking at Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views?

On-site parking is available at the property.

What time is check-in at Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views?

Check-in begins at 4:00 PM.

What time is check-out at Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views?

Checkout is at 11:00 AM.

Where is Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views located?

Situated in the mountains, this cottage is 1.8 mi (2.9 km) from Pollak Vineyards and within 6 miles (10 km) of Shenandoah National Park and Valley Road Vineyards. King Family Vineyards and Crozet Tunnel are also within 6 miles (10 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. 45 out of 46 reviews
Rating 8 - Good. 1 out of 46 reviews
Rating 6 - Okay. 0 out of 46 reviews
Rating 4 - Poor. 0 out of 46 reviews
Rating 2 - Terrible. 0 out of 46 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Karen A.

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

Always Fabulous

I always enjoy my stay here. The comfy coziness of the house, the beautiful grounds, the friendliness of Matt the groundskeeper- always accessible and accommodating! A great location for all the activities.
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Sarah K.

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

Cozy and so beautiful

We love this cottage!!
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Kelsey P.

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

Perfect location and views in Charlottesville area

My family and I truly enjoyed this property. The rooms were lovely and the views can't be beat. You're so close to area attractions like vineyards, breweries, and hikes.
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Erin S.

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

Adorable house

We loved staying here. The views from the back enclosed porch were spectacular. The house had such great little details and great decor! Well stocked kitchen and comfy beds. A perfect place for my friends and I to have a great girls weekend.
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Melissa B.

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

A great space for families

Came to the area for a wedding, this space was perfect for our family. Our toddler loved running around the outdoor area and our baby loved the screened in porch area. Gorgeous views of the mountains. The property manager was helpful and easy to reach. Couldn’t recommend this house more!
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Harry S.

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

Ramsay cottage

Loved walking the estate and the real fireplace
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Sarah P.

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

Another great stay at Ramsay Estates

I can’t say enough good things about this cottage. So comfortable with plenty of room to spread out. The grounds are stunning. This was our second stay and we will return!
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Verified traveller

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

Enjoyed the stay

This property was very comfortable and in a great location. The view from the screened in porch was fantastic. The property manager was very responsive and the cottage had all the amenities you could need. The blue berry muffins and fresh fruit were a nice touch. We are looking forward to our next trip and staying with you in the future.
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

Sharon M. P.

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

Family Wedding Destination

We rented two properties to accommodate 3 families from Michigan for a family wedding in the area. Outstanding experience! Such a quaint welcoming home!
Stayed 4 nights in Oct 2024
Verified

10/10 Excellent

Karen A.

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

Absolute Perfection

Fantastic location, serene property, adorable cottage, property manager, Matt, was a truly magnificent host; very friendly, knowledgeable, gave us a tour of the property, just super nice and accommodating. House was clean, all the amenities were there, just what our family needed to relax and get away from our usual hustle. Truly can't wait to come back!
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Sarah P.

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

Clean and Quaint Cottage

Perfect space for our family while we visited our UVA student. The 15 minute ride was worth it for the space and serenity. The cottage had everything we needed; super clean; beautiful grounds; great communication. We will be back!
Stayed 2 nights in Nov 2023
Verified

10/10 Excellent

Haven P.

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

Great Place. Everything as expected.

The listing is accurate. Everyone involved was helpful. There were only two of us but the house would have supported more.
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Shari B.

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

Guest Cottage on the Ramsey Estate

The cottage is just so charming. Amenities and the property manager where excellent made sure we had everything. Close to wineries and trail hikes, gift stores and restaurants. The chickens, rooster and cows are adorable. We had fun feeding them and walking some trails right on the property!! We will be back this was our second time staying on the Ramsey Estate.
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Ian N.

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

Beautiful Views and Wonderful Charm

The home and location were even better than described. The beds were comfortable, the kitchen well stocked, and the whole place thoughtfully decorated. We especially loved cool fall evenings by the rustic outdoor fireplace and morning coffee on the screen porch. Beyond the cottage itself, we also enjoyed exploring the rest of the estate, visiting the chickens and cows, and walking in the vineyard. We will definitely stay here again when we are back in Charlottesville.
Stayed 5 nights in Oct 2023
Verified

10/10 Excellent

Henry H.

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

Consultant

Wonderful
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Julie B.

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

Graduation 2023

Our family was able to spend the weekend of UVA graduation in this lovely home on the historic Ramsey Estate. It was a peaceful, dreamy retreat and the perfect place to celebrate an important event. The living room and porch and outside areas were perfect for gathering. The kitchen was well-supplied and the manager was friendly and generous. The interior was absolutely adorable and beyond comfortable. We can't wait to return.
Stayed 4 nights in May 2023
Verified

10/10 Excellent

Laura F.

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

Beautiful setting and perfect location to explore local wineries!

This house was set on a beautiful estate close to many wineries. The view from the screened in back porch was amazing. We loved the house although the kitchen did not have some of the basics that I’m accustomed to seeing: basic spices like salt and pepper, sugar, olive oil. So be prepared if you plan to cook. The bed in the king sized room was really two twins put together in an off way that made the middle arch up. Really though, other than those two things, it was the perfect house for our group. Highly recommend!
Stayed 3 nights in Apr 2023
Verified

10/10 Excellent

Elbridge G.

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

An absolute bit of fantastic!

An experience without equal and one for which I shall always pine. One which lacked even the slightest inkling of something about which to complain, yet if under durress, I had to lodge any, my quips would be that our stay was far too short and that I couldn't buy the Ramsay Cottage. Regardless, Matt, the property's exceptional overseer, was fantastic. He had everything ship shape and bristol fashion upon our arrival and communicated splendldly throughout our stay. We wanted for nothing at all, save more time at this truly grand and beautiful place, one to which I know we shall return again.
Stayed 2 nights in Mar 2023
Verified

10/10 Excellent

Scott R.

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

Great VA countryside getaway

Beautiful property. Stayed here with our two young kids, and the grandparents, for a relaxing birthday weekend getaway. Two main bedrooms were perfect for the adults and the upstairs bedroom was perfect for our kids. Spent most of our time just relaxing in the screened-in porch for coffee and breakfast in the mornings and dinner in the evenings, enjoying the great view of the countryside.Location is ideal, as it’s a straight drive down the road to UVA, and closely situated near many of the local wineries.The cottage had everything we needed.Only thing to request would be a new grill. Two were there. One was rotted out and unusable. The other was functioning but in deteriorating condition and hadn’t been cleaned so the grease flames prevented us from adequately being able to use it despite the nice weather. But, I won’t let this detract from an otherwise great property that we would happily return to.
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Hilary S.

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

As charming the Pictures!

I fell in love with this property from the first photo, and it was just as I had hoped and imagined. A charming cottage in a bucolic setting, whimsically decorated and truly comfortable. We rented all three properties located at Ramsay Estate for our family to attend a wedding held in Crozet. This cottage was where we all had coffee together and planned our days. Being able to sit on that screened porch, overlooking the fields and changing leaves was a perfect start to each day. A living room and a separate sitting area gave enough room for all dozen of us to relax, and since we ate our dinners out, there was no need for a large dining table; the three smaller tables sufficed, and enabled us to mix it up a bit for catch up. The Cottage was immaculate, as were all the homes, and extremely comfortable. The kitchens were well appointed, and the beds ensured a good nights sleep. Matt, the property manager was extremely responsive, and could not have been nicer. One bulb burned out while we there and it was taken care of asap. Really excellent support. I highly recommend this property.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Janet S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
great experience
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Leslie R.

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

Perfect Setting

The house was beautiful and better than described. It's a quaint older farmhouse that's been updated and very well decorated. The scenery was beautiful and we had the run of the entire estate. The farm manager even built us a fire in the outdoor fireplace. We plan to come back.
Stayed 3 nights in Dec 2022
Verified

10/10 Excellent

Joanne L.

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

Gorgeous Property

This is a charming cottage located on a historic estate with fabulous views of the mountains. The cottage is beautifully decorated, impeccably maintained and extremely comfortable (including the beds!). We would definitely stay again!
Stayed 3 nights in Nov 2022
Verified

10/10 Excellent

Amy K.

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

Not a cookie cutter experience

This is not a cookie-cutter property. The house is beautifully decorated with high-quality fabrics and lots of unique touches. The views are amazing and the property extremely well-maintained with a great outdoor firepit space. If you're looking for a great weekend getaway with friends or family in a beautiful setting that's centrally located to wineries, this is your spot.
Stayed 2 nights in Oct 2022
Verified

10/10 Excellent

Marisa F.

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

Great winery location

We had a wonderful weekend. The views from the property are simply stunning. The outdoor fireplace is wonderful. We sat out there each night of our stay and enjoyed the countryside. I would highly recommend this house for your trip to Charlottesville!
Stayed 2 nights in Oct 2022

About the host

Hosted by Guesthouses

Host profile image
We're Guesthouses, a Virginia-based vacation rental management company with deep roots in the community. Founded in 1976, we're proud to be the oldest and most established vacation rental company in the area, with decades of experience caring for homes and hosting guests.

We manage each property as if it were our own, working closely with homeowners and focusing on what truly matters to guests: clean and comfortable spaces, thoughtful details, clear communication, and responsive local support. Our long-standing presence means we know these homes, these neighborhoods, and this region exceptionally well.

Whether you're here for a relaxing getaway, a family visit, or a special occasion, our goal is to provide a seamless, welcoming stay and genuine hospitality from start to finish. We're local, available, and always happy to share recommendations or assist with anything you need to make the most of your time here.

We look forward to hosting you and helping you unlock, explore, and enjoy everything the area has to offer.

Premier Host

They consistently provide great experiences for their guests
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