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Compare 360 Vacation Homes in Roseburg with updated reviews, rates, and availability.

Railroad District, steps to downtown, everything you need to enjoy Ashland!
Front of main house on Second Street

Railroad District, steps to downtown, everything you need to enjoy Ashland!

10.0 out of 10, Exceptional, (136)
"Clean. Tidy. comfortable. Well appointed. But we left a pair of walking polls behind and would like Sugar to keep them for us and we will pick them up when we stay again in the fall of 2025. David Roberts"
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Premier Downstairs Flat in Perfect Down Town Location
Exterior

Premier Downstairs Flat in Perfect Down Town Location

10.0 out of 10, Exceptional, (47)
"This was a beautiful and clean home in a perfect location. So close to downtown and the Shakespeare Festival. The walk was easy, well lite and safe. The home was clean and the beds were comfortable. We would definitely recommend and return!!"
Premier Downstairs Flat in Perfect Down Town Location
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Cozy up with a book or your favorite movie & unwind on our chic and comfy couch.

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

9.8 out of 10, Exceptional, (23)
"Gary was amazing, the house was super clean and well stocked. I was on a work trip so i was only there in the evenings, but it was perfect! Id love to ce back!"
The price is AED 476
AED 1,108 total
includes taxes & fees
5 Jan - 6 January 2025
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Charming home, w/hot tub, close to downtown Pet-Friendly!
Interior

Charming home, w/hot tub, close to downtown Pet-Friendly!

10.0 out of 10, Exceptional, (33)
"We had a one night stay at this property with our two dogs on our way to Southern California and met all of our needs. Wonderful fence yard front and back of the house. Wonderful communication with the manager/owner. We had a great time."
The price is AED 643
AED 1,757 total
includes taxes & fees
4 Jan - 5 January 2025
Charming home, w/hot tub, close to downtown Pet-Friendly!
The Rellik House and Winery
Front of property

The Rellik House and Winery

3.5 star property
9.4 out of 10, Exceptional, (3)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
The price is AED 529
AED 1,235 total
includes taxes & fees
5 Jan - 6 January 2025
The Rellik House and Winery
Pet-Friendly Medford Vacation Rental w/ Yard!
Medford Vacation Rental | 4BR | 2BA | 1,694 Sq Ft | 2 Steps to Access

Pet-Friendly Medford Vacation Rental w/ Yard!

9.2 out of 10, Wonderful, (7)
"Great cozy location"
Pet-Friendly Medford Vacation Rental w/ Yard!
Spacious Western Home on 2 acres in the Pines close to Crater Lake
Exterior

Spacious Western Home on 2 acres in the Pines close to Crater Lake

10.0 out of 10, Exceptional, (95)
"Nice place easy to relax with family."
The price is AED 551
AED 1,243 total
includes taxes & fees
30 Dec - 31 Dec
Spacious Western Home on 2 acres in the Pines close to Crater Lake
Secluded Luxury Mtn Getaway Near Crescent Lake!
Crescent Vacation Rental Home | 4BR | 3BA | 3 Stories | 3,828 Sq Ft

Secluded Luxury Mtn Getaway Near Crescent Lake!

9.8 out of 10, Exceptional, (30)
"Huge house with lots of room for family to spread out. Great location for touring area. Day trips to Bend and then Crater Lake. Hot tub was a nice extra well used. Only one shower besides one in master wasn’t ideal for 7 adults but worked out. We lived bonus living space sun room. Made a great yoga studio."
Secluded Luxury Mtn Getaway Near Crescent Lake!
A Restful Studio Near a Creek and Forest - Pets
Everything you need in one room!

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (22)
"Great place, comfortable and clean. The host was very polite."
The price is AED 349
AED 606 total
includes taxes & fees
2 Jan - 3 January 2025
A Restful Studio Near a Creek and Forest - Pets
Jacksonville Mountain Retreat

Jacksonville Mountain Retreat

9.6 out of 10, Exceptional, (61)
"This is a very nice home. "
Jacksonville Mountain Retreat
The Phoenix House- a place to relax and rejuvenate
Interior

The Phoenix House- a place to relax and rejuvenate

8.8 out of 10, Excellent, (6)
"We have stayed there twice now. Our art gallery reception was last night in Medford. Today I visited a friend in Ashland. Debbie’s Diner is very close for breakfast and Starbucks down the road. The house has an elegant feel to it, high ceilings and lots of windows to the backyard. Thank you so much."
The Phoenix House- a place to relax and rejuvenate
ZZ ZANY ZOO II - Townhome, with Carport & Garage
Living Room/Roku Tv

ZZ ZANY ZOO II - Townhome, with Carport & Garage

10.0 out of 10, Exceptional, (78)
"Fun place, clean, quiet. Great host. "
ZZ ZANY ZOO II - Townhome, with Carport & Garage
The Bucket List Retreat
Exterior

The Bucket List Retreat

9.6 out of 10, Exceptional, (24)
"Comfy beds, great location to our activity, accommodating owner who went out of their way to send us something we left behind. Would definitely stay a this property again."
The price is AED 688
AED 1,642 total
includes taxes & fees
5 Jan - 6 January 2025
The Bucket List Retreat
Indigo Collective - Modern Home
Living area

Indigo Collective - Modern Home

10.0 out of 10, Exceptional, (9)
"Adorable & very comfortable."
The price is AED 782
AED 1,773 total
includes taxes & fees
31 Dec - 1 January 2025
Indigo Collective - Modern Home
Hanna's House | 1 block to downtown!
Enjoy your morning coffee in the sunny bay window

Hanna's House | 1 block to downtown!

10.0 out of 10, Exceptional, (160)
"This is a wonderful little space that's within a block of old town Ashland and all its restaurants, coffee shops, and theaters. Wonderful helpfulness and communication from our host, and the space had everything we needed - all with modern remodeling, it seems. We loved it!"
The price is AED 509
AED 1,072 total
includes taxes & fees
5 Jan - 6 January 2025
Hanna's House | 1 block to downtown!
California Cottage: Downtown!

California Cottage: Downtown!

9.6 out of 10, Exceptional, (19)
"The property was so cozy. Exactly like the listing description. Literally a few steps from downtown Jacksonville. Everything that we hoped for!"
The price is AED 528
AED 973 total
includes taxes & fees
1 Jan - 2 January 2025
California Cottage: Downtown!
230-Downstairs-Duplex-Private Bathroom-Mountain View
Exterior

230-Downstairs-Duplex-Private Bathroom-Mountain View

9.8 out of 10, Exceptional, (17)
"Quiet neighborhood; convenient parking; great HVAC system; comfy beds; hot shower; good wine. Owner gives codes day of stay. "
230-Downstairs-Duplex-Private Bathroom-Mountain View
Cheerful 3-Bedroom home in Central Point
Room

Cheerful 3-Bedroom home in Central Point

10.0 out of 10, Exceptional, (17)
"This house is in a very nice, quiet neighborhood but really centrally located to surrounding amenities. A beautiful and clean home - love the way it is decorated!! Jill was a great host. Her response time to any communication was almost instant."
Cheerful 3-Bedroom home in Central Point
Brookdale Meadows sleeps 6
Relax in main Living room with open concept.

Brookdale Meadows sleeps 6

10.0 out of 10, Exceptional, (14)
"Four adults stayed at the house. We were in Medford to visit our family matriarch. We enjoyed spending the evening together cooking dinner, sharing a meal and visiting. The house is the best! Clean, comfortable and so well appointed with quality linens, towels abd cookware."
Brookdale Meadows sleeps 6
Agency Lake Property with View of lake from your front Porch in Chiloquin Oregon
Property grounds

Agency Lake Property with View of lake from your front Porch in Chiloquin Oregon

10.0 out of 10, Exceptional, (59)
"We were in the area for Ride the Rim and property was great - easy access to Crater Lake and nice relaxing place to stay. Maighread was easily available and offered local suggestions. Would stay here again!"
Agency Lake Property with View of lake from your front Porch in Chiloquin Oregon
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Roseburg

Firewater Lodge Cabin Experience
Exterior

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (45)
"We loved everything about our stay here!! Wonderful communication with our host, clean, and quiet were some of our first impressions! Check-in and checkout were simple and everything I could have thought of as a question is answered for me before I think of it. Open and comfortable living area made for a great movie night. We enjoyed playing in the creek and sitting by the fire pit! The kitchen was fully stocked, so appreciated! The beds provided plenty of space for all of us and everyone...
Firewater Lodge Cabin Experience
Crater Lake Resort
Property grounds

Crater Lake Resort

3.0 star property
8.6 out of 10, Excellent, (390)
"Excellent!"
The price is AED 459
AED 506 total
includes taxes & fees
3 Jan - 4 January 2025
Crater Lake Resort
Rocky Point Resort
Front of property

Rocky Point Resort

2.5 star property
8.2 out of 10, Very Good, (342)
"This was a wonderful property. Clean quiet and sun rises amazing. No dining as stated in check in informaion made difficult. Communication was difficult but we got help from 140 store. Overall this place exceeded expectations. Thx to all who helped."
The price is AED 386
AED 438 total
includes taxes & fees
30 Dec - 31 Dec
Rocky Point Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.