One of the few properties with video games available for guests.
Discover nearby landmarks
Walk to Weisinger Family Winery
4 bedrooms4 bathroomsSleeps 12
Popular amenities
Private pool
Spa pool on site
Onsite parking available
Dog-friendly
Kitchen
Washing machine
Explore the area
Ashland, OR
Weisinger Family Winery
Place, Weisinger Family Winery
17 min walk
Southern Oregon University
Place, Southern Oregon University
4 min drive
Oregon Shakespeare Festival
Place, Oregon Shakespeare Festival
8 min drive
Medford, OR (MFR-Rogue Valley Intl.)
Airport, Medford, OR (MFR-Rogue Valley Intl.)
22 min drive
Rooms & beds
4 bedrooms (sleeps 12)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Single Bunk Beds
Bedroom 4
1 King Bed
4 bathrooms
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Bathroom 3
Bathtub · Toilet · Shower only
Bathroom 4
Bathtub · Toilet · Shower only
Spaces
Kitchen
Office
Garden
About this property
Luxury Ashland Mountain Escape: Pool, Hot Tub
Summary:
Live the Southern Oregon paradise life at the Jefferson Estate — a fabulously appointed home on 8 acres, perfect for group getaways or small gatherings.
Take in views of Grizzly Peak while fishing in the small stocked pond, or soak in the seasonal outdoor pool or hot tub while enjoying the quiet of nature.
Play games on the lawn, read by the living room fireplace, or try your hand at the billiards table.
The kitchen is fully equipped to live out all your entertaining dreams, and a screened sun porch provides the perfect setting for late afternoon noshes and nibbles. A Swank House property.
The Space:
Jefferson Estate is a four bedroom, single-level home that’s ideal for family getaways, girls’ weekends, book clubs, weddings, and reunions. Twelve people sleep comfortably, and sleeping pads are available for crashing by the gas fireplace or out on the screened patio.
The generous open living spaces welcome you and your guests to relax, entertain, eat, drink, play games and enjoy good company. Our biggest hope is that you’ll make yourself comfortable in this luxurious home away from home.
Guest Access:
You have the place to yourself.
The Neighborhood:
Located on 8 acres yet only 3 miles to Oregon Shakespeare Festival. Jefferson Estate is close in and private for your whole group. Please note that you may see our horse staff off in the distance training or giving lessons in the horse arena. The residence is located at the back of the property with gate access only to the home.
Getting Around:
Jefferson Estate sits conveniently just minutes from the South Ashland I-5 freeway entrance (although you’ll feel like you’re miles away from anyone). It’s really the best of both worlds — you’ll feel like you are in the country, but only steps away from the action of downtown Ashland’s famous food and theatre scene.
We’re also just a few minutes from Emigrant Lake, and several local wineries. In fact, you can walk to Weisinger Family Winery (about .5 miles away), and drive to Irvine and Roberts tasting room (a favorite!) in a matter of minutes.
This home is approximately 8-minutes from downtown Ashland’s Plaza and the Oregon Shakespeare Festival theatre.
Other Things to Note:
A note for families with littles: the pool, hot tub and pond are not fenced-in from the rest of the property. Please be extra attentive with small children around this home’s open bodies of water.
No Swimming in the pond.
Bring your own fishing poles for bass and bluegill
IMPORTANT: Jefferson Estate is professionally maintained to provide a comfortable and enjoyable experience for every guest.
Routine landscaping service is typically scheduled on Monday mornings during standard business hours. Depending on seasonal needs, maintenance may last approximately 1–3 hours and can include the use of lawn equipment.
Pool maintenance is also performed periodically during daytime hours to help keep the pool clean, safe, and ready for guest use. Whenever possible, these services are scheduled between reservations or while guests are away from the property.
The estate is located on a larger rural property adjacent to irrigated pastureland. In rare cases, neighboring property owners or utility personnel may need access to nearby areas for emergency irrigation or agricultural-related maintenance. While these situations are uncommon and outside of our control, we do our best to minimize any disruption and coordinate work around guest stays whenever possible.
We understand that privacy is an important part of your experience and work closely with all service providers to maintain the property with minimal interruption. We appreciate your understanding as we care for the estate to the high standards our guests expect.
Lost & Found policy:
1. We will hold found items for up to 30 days after your checkout date.
2. If you'd like the item shipped, you'll be responsible for the shipping cost plus a $25 handling and management fee, which covers locating, storing, and coordinating the return.
3. If you're planning to return to the area, we're happy to hold your item for pickup within the 30-day holding period.
4. Any unclaimed items remaining after 30 days may be donated or disposed of.
Interaction with Guests:
We take your privacy very seriously and do not intrude on your vacation. However, if you need any assistance, we are here to help and are always available by text.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Historic Dunn Ranch Ashland Oregon. Sleeps 12 to 14 Great for large groups.
Ashland
Historic Dunn Ranch Ashland Oregon. Sleeps 12 to 14 Great for large groups.
Ashland Group Retreat! The RedTail Inn offers 3 full suites within one booking, sleeping up to 12. Great location for the Shakespeare Festival. Ample space for your large family or friend group.
Siskiyou-Hargadine Historic District
Ashland Group Retreat! The RedTail Inn offers 3 full suites within one booking, sleeping up to 12. Great location for the Shakespeare Festival. Ample space for your large family or friend group.
Events allowed: family gatherings and birthday parties
default
Pets
Pets allowed: dogs (limit 1 total)
Charge may apply
default
Smoking
Smoking is not permitted
Please do not exceed maximum occupancy. Failure to do so may result in removal from property with no refund.
Important information
You need to know
Property # 3903229vb
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: 12
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 and a first aid kit
About the area
Ashland
Located in Ashland, this villa is in the mountains and on the waterfront. The area's natural beauty can be seen at North Mountain Park and Cascade-Siskiyou National Monument, while Oregon Shakespeare Festival and Schneider Museum of Art are cultural highlights.
Oregon Shakespeare Festival - 8 min drive - 7.2 km
Lithia Park - 8 min drive - 7.2 km
Getting around
Medford, OR (MFR-Rogue Valley Intl.) - 27 min drive
Restaurants
Dutch Bros Coffee - 5 min drive
Taco Bell - 4 min drive
Xerxes Mediterranean Grill - 4 min drive
Wild Goose Cafe & Bar - 4 min drive
Oak Tree Northwest Bar & Grill - 4 min drive
Frequently asked questions
Does Luxury Ashland Mountain Escape: Pool, Hot Tub have a pool?
Yes, this property has a pool.
How much does it cost to stay at Luxury Ashland Mountain Escape: Pool, Hot Tub?
As of 2 August 2026, prices found for a 1-night stay for 2 adults at Luxury Ashland Mountain Escape: Pool, Hot Tub on 27 September 2026 start from NZ$2,991, 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.
Is Luxury Ashland Mountain Escape: Pool, Hot Tub pet-friendly?
Yes, this property allows dogs (limit 1 total).
How much is parking at Luxury Ashland Mountain Escape: Pool, Hot Tub?
On-site parking is available at the property.
What time is check-in at Luxury Ashland Mountain Escape: Pool, Hot Tub?
Check-in begins at 3:00 PM.
What time is check-out at Luxury Ashland Mountain Escape: Pool, Hot Tub?
Checkout is at 11:00 AM.
Where is Luxury Ashland Mountain Escape: Pool, Hot Tub located?
Situated on the waterfront, this villa is 0.8 mi (1.2 km) from Weisinger Family Winery and 3 mi (4.9 km) from Southern Oregon University. Schneider Museum of Art and Emigrant Lake are also within 6 miles (10 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This property was wonderful for our family of 5 teens. The kitchen was well stocked, beds comfortable and it also had a nice quiet and calm feel. Can't wait to come back.
Every Swank House’s unique history and architecture has guided its updated design. We honor each home’s narrative while turning up the dial on its comfort and conveniences. From mid-century modern to contemporary Victorian, every design decision has been influenced by best parts of a home’s past. We get our kicks from the challenge of authentic restoration, balanced with stylish design for the modern traveler.
What makes this property unique
This Ashland gem is truly one of a kind. With ample space to spread out and come together, Jefferson Estate will be the perfect backdrop for your group vacation or special event. The kids will stay busy with indoor and outdoor games (Pac-Man and bocce ball), while adults will love the quiet conveniences — soaking tubs, plush bedding, gas fireplace, and views you won’t find anywhere else in Southern Oregon. Live the Southern Oregon paradise life at the Jefferson Estate — a fabulously appointed home on 8 acres, perfect for group getaways and wedding parties. Take in views of Grizzly Peak while fishing in the small stocked pond, or soak in the seasonal outdoor pool or hot tub while enjoying the quiet of nature (and soothing babble of the backyard’s water feature). Play games on the lawn, read by the living room fireplace, or try your hand at the billiards table. The kitchen is fully equipped to live out all your entertaining dreams, and a screened sun porch provides the perfect setting for late afternoon noshes and nibbles.
Premier Host
They consistently provide great experiences for their guests