Entire home

Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views

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

A grassy outdoor area with three wooden chairs under a tree, overlooking a hilly landscape. - Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views (Greenwood)
A garden pathway surrounded by neatly trimmed hedges and a variety of plants. - Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views (Greenwood)
A two-story house with a front porch, a garage, and a well-maintained lawn. - Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views (Greenwood)
A cozy room with a round wooden table, cushioned seating, and a view of greenery through large windows. - Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views (Greenwood)
A living room with a sofa, a dining table, and chairs. There is a painting on the wall and a window with curtains. - Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views (Greenwood)
You can look forward to free breakfast, a garden, and laundry facilities at Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 62500 sq ft

Popular amenities

  • Breakfast included
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Add dates for prices

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!

    Bookings for 3 or more nights include complimentary access to The Greencroft Club for pool, racquet sports, and dining. Please note that a booking and confirmation agreement will also be sent via email/text to review and sign upon booking.

    Hosted by VA Guesthouses

Property amenities

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Free breakfast available
  • Chef service
  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • DVD player
  • Smart TV with cable/satellite channels

Outdoor areas

  • Garden
  • Gas grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Concierge services
  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • In a rural location
  • In the mountains

Things to do

  • Basketball nearby
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Mountain biking nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

General

  • Garden
  • Housekeeping (on request)
  • Unit size: 2,500 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

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

Pets

Pets not allowed

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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

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, hiking/biking trails, and mountain biking nearby. Visit our Greenwood travel guide
View more Cottages in Greenwood
Map
Greenwood, VA

What's nearby

  • A body of water reflecting sunlight with clouds in the sky.
    Pollak Vineyards
    3 min drive - 3.5 km
  • A picnic setup with a bottle of King Family Viozner wine, snacks, and a bottle of Reddi Wip.
    King Family Vineyards
    6 min drive - 8.2 km
  • A vineyard with rows of grapevines, a wooden barn, and autumn-colored trees in the background.
    Veritas Vineyard and Winery
    7 min drive - 12.3 km
  • Valley Road Vineyards
    3 min drive - 6.3 km
  • Blue Ridge Parkway North Entrance
    6 min drive - 10.4 km

Getting around

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

Restaurants

  • Chiles Peach Orchard
    6 min drive
  • Blue Mountain Brewery
    5 min drive
  • King Family Vineyards
    9 min drive
  • The Yellow Mug
    9 min drive
  • Mudhouse
    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 is parking?

Onsite 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?

Check-out 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 mi (10 km) of Shenandoah National Park and Chiles Peach Orchard. Valley Road Vineyards and King Family Vineyards are also within 6 mi (10 km).

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Ramsay Estate Cottage – Historic Vineyard Retreat with Mountain Views 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. 46 out of 48 reviews
Rating 8 - Good. 1 out of 48 reviews
Rating 6 - Okay. 1 out of 48 reviews
Rating 4 - Poor. 0 out of 48 reviews
Rating 2 - Terrible. 0 out of 48 reviews

9.8

Cleanliness

10

Location

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
An exceptional property! It is quite historic and unique. The cottage is attractive, well decorated and nestled amidst gorgeous farmland/ mountain scenery. This was a perfect home for my family (including children) to stay during a recent wedding weekend, making our time even more memorable for all. Thank you to our gracious hosts.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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

Cozy and so beautiful

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Consultant

Wonderful
Stayed 2 nights in May 2023
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

6/10 Okay

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Ramsey Estate has beautiful scenery out the back. It's quiet. The decor was really fun and unique. Beds were comfortable. The house has a lot of character and space. It's an older estate.
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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