Jackson Area Rentals
From $467 per night (USD)VRBO
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Wake to breathtaking sunrises over the rolling hills! Front sitting area and fire pit offer the perfect spot for mornin ...
From $467 per night (USD)VRBO
From $144 per night (USD)Expedia
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
33 foot RV on 3/12 acre gated property, surrounded by rolling hills of vineyards and wine estates. Fruit trees, gardens, ...
From $144 per night (USD)Expedia
From $254 per night (USD)VRBO
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wake to breathtaking sunrises over the rolling hills! Front sitting area and fire pit offer the perfect spot for mornin ...
From $254 per night (USD)VRBO
From $156 per night (USD)VRBO
Adventure Getaway/Spacious One Bedroom in Beautiful Central Point, Oregon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay comfortably in Central Point at this 1-bedroom unit. The bedroom overlooks a farm as well as views to Mount McLough ...
From $156 per night (USD)VRBO
From $170 per night (USD)VRBO
Beautiful Setting w/ Pool, Hot Tub & Golf Views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Relax and recharge in this peaceful private studio guest house, perfectly situated on the beautiful Rogue Valley Country ...
From $170 per night (USD)VRBO
From $134 per night (USD)Expedia
Cozy 3-Bed Home | Patio, W/D, Yard & Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy a summer getaway in this renovated 3BR/1.5BA Medford home! Cool off in A/C, relax outside by the fire pit, and coo ...
From $134 per night (USD)Expedia
From $249 per night (USD)VRBO
Cozy Log Cabin in the Applegate Valley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the serene beauty of the Applegate Valley in this cozy 2-bedroom, 2-bathroom log cabin nestled among the vines ...
From $249 per night (USD)VRBO
From $220 per night (USD)Expedia
RIVERLIFE ON THE ROGUE RIVER
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
RIVERLIFE is waiting for you at this phenomenal private beach oasis. Watch our Osprey, “walley”, catch trout and steelhe ...
From $220 per night (USD)Expedia
From $123 per night (USD)VRBO
Cozy 1-bedroom apartment in awesome Medford with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This fully furnished one-room apartment offers a quiet, comfortable retreat in a beautifully preserved historic home min ...
From $123 per night (USD)VRBO
From $140 per night (USD)Expedia
Ashland Garden Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perfect for a romantic getaway or a peaceful retreat. Come experience the beauty and charm of Ashland in this cozy cott ...
From $140 per night (USD)Expedia
From $151 per night (USD)VRBO
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to The White Rabbit Retreat — a peaceful guesthouse just 5 minutes from Jacksonville. Surrounded by open fields ...
From $151 per night (USD)VRBO
From $269 per night (USD)Expedia
4-bedroom house in lovely Medford with AC, Close to Rogue X, beautiful patio.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Consider this house your home away from home while you visit Medford. This terrific property boasts 4 bedrooms, includin ...
From $269 per night (USD)Expedia
From $151 per night (USD)VRBO
Fish, Raft & Hike: Southwest OR Couple’s Retreat!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step-Free Access | BBQ Ready | Mountain Views Escape the hustle and bustle with your loved one and book this 1-bathroom ...
From $151 per night (USD)VRBO
From $144 per night (USD)VRBO
Lori Lane House
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
5 Blocks from downtown Ashland! The space This is a two story home. One bedroom with a queen bed and private bath locate ...
From $144 per night (USD)VRBO
From $99 per night (USD)VRBO
Juliet Cottage - 2 bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Ashland, this adorable cottage is a dream. With 2 cozy bedrooms and a refreshing bathroom, guests will feel r ...
From $99 per night (USD)VRBO
From $300 per night (USD)Expedia
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We are delighted to share our family's second home with other Ashland-lovers and hope you find it to be a happy place f ...
From $300 per night (USD)Expedia
From $297 per night (USD)VRBO
Pet friendly 3 Bedroom home near Jacksonville
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Minutes away from the Historic town of Jacksonville & downtown Medford. Constructed around the early 1900's the home has ...
From $297 per night (USD)VRBO
From $81 per night (USD)VRBO
Historic Water Tower
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Medford at this lovely house. This phenomenal property features 2 bedrooms with a cozy queen bed and a comfort ...
From $81 per night (USD)VRBO
From $358 per night (USD)VRBO
4 Bedroom Home in the Heart of the Historic- Jacksonville, OR
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled right in the heart of the historical district in Jacksonville, OR, This mid century modern retreat offers all th ...
From $358 per night (USD)VRBO
From $166 per night (USD)Expedia
The Monarch - charming cottage in prime downtown Jacksonville w/AC + luxury bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to this charming cottage in Jacksonville. This marvelous one-bedroom retreat features a cozy king bed, a well-eq ...
From $166 per night (USD)Expedia
From $378 per night (USD)VRBO
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience timeless charm in this fully renovated 2BR, 1.5BA home inspired by historic Williamsburg architecture. With 8 ...
From $378 per night (USD)VRBO
From $483 per night (USD)Expedia
Relax, Reconnect, Explore Scenic Retreat + Pool, Treehouses & Adventure Nearby
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Enchanted Escape at the Foot of Table Rock – Sleeps 8+ Discover a hidden gem tucked beneath the majestic Lower Table Roc ...
From $483 per night (USD)Expedia
From $217 per night (USD)VRBO
Immaculate and private 2-bedroom house, close to everything, pet friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover this beautiful new 2-bedroom gem minutes away from Medford. This charming house features 1 king bed and 1 queen ...
From $217 per night (USD)VRBO
From $274 per night (USD)Expedia
Charming 1-bedroom cottage in welcoming Ashland with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your cozy cottage in Ashland with 1 bedroom is the perfect retreat for guests seeking a charming and lovely getaway. Equ ...
From $274 per night (USD)Expedia
From $292 per night (USD)VRBO
The Siskiyou House
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Medford Oregon! This updated two story, smoke free home has 5 bedrooms with brand new memory foam mattresses ...
From $292 per night (USD)VRBO
From $170 per night (USD)Expedia
River Bend Cottage 1-bedroom Barndominium with Wildlife Abounding
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This brand new 1-bedroom cottage in Shady Cove is perfect for your escape. The cozy space features a lovely king bed and ...
From $170 per night (USD)Expedia
From $255 per night (USD)VRBO
Peaceful Forest Recreation Retreat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Relax and recreate with family and friends at this peaceful retreat in the woods. Built in 1940, this beautifully restor ...
From $255 per night (USD)VRBO
From $255 per night (USD)Expedia
Charming Lovely 1940s Bungalow
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Take it easy at this unique and tranquil getaway in Ashland Oregon. Nestled in the heart of Southern Oregon, Ashland is ...
From $255 per night (USD)Expedia
From $173 per night (USD)VRBO
Beautiful Log Home with City View!! 2 bedroom 2 bath home in the mountain woods.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for a quiet and serene place to stay, look no further! Our log home in the woods is a prefect choice to be away ...
From $173 per night (USD)VRBO
From $116 per night (USD)VRBO
Amazing Tiny Home On The Pristine Applgate River In Beautiful Southern Oregon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience a one-of-a-kind getaway on the pristine Applegate River, where serenity, sustainability, comfort and adventur ...
From $116 per night (USD)VRBO
From $661 per night (USD)VRBO
Spacious farmhouse in close proximity to vineyards; great for large groups
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 20
Welcome to this charming farmhouse in Talent. This beautiful property boasts 7 bedrooms, including 2 king beds, 2 queen ...
From $661 per night (USD)VRBO
From $158 per night (USD)Expedia
Rosewood Studio by WanderLodges
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the *NEW* Rosewood Studio A cozy space just minutes from downtown, offering ultimate privacy with your o ...
From $158 per night (USD)Expedia
From $205 per night (USD)VRBO
East Medford Home Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in a charming cul-de-sac in E Medford, this beautiful home offers a relaxing atmosphere throughout and is suited ...
From $205 per night (USD)VRBO
From $231 per night (USD)Expedia
Owl Creek Cabin Mountain Getaway near Ashland, Oregon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This property is a secluded mountain getaway in the Southern Cascades near Ashland Oregon. The cabin is stocked with dis ...
From $231 per night (USD)Expedia
Click For PricingVRBO
Historic Heritage House in the heart of Ashland! Walking distance to downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Heritage House at Second Street Cottages! Located in the historic railroad district, walking distance to ...
Click For PricingVRBO
From $487 per night (USD)Expedia
Private vineyard sanctuary for 6. Savor coffee at sunrise in the backyard oasis, soak in the hot tub under starry skies, and enjoy this elegant spacious retreat with mountain views, minutes from Historic Jacksonville and Applegate’s wine country.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked in a private valley at the base of Woodrat Mountain, Starry Oak is a 41-acre estate offering seclusion, sweeping ...
From $487 per night (USD)Expedia
From $510 per night (USD)VRBO
Railroad District, steps to downtown, everything you need to enjoy Ashland!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This delightful cottage in Ashland is a charming retreat for guests. With 2 cozy bedrooms featuring 2 queen beds and 1 t ...
From $510 per night (USD)VRBO
From $173 per night (USD)Expedia
Walk to Rogue X: Medford Family Home w/ Large Yard
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Near Water Park, Events & Sports | Covered Patio | Dog Friendly w/ Fee This Medford vacation rental your gateway to Sou ...
From $173 per night (USD)Expedia