This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Ashland Vacation Rentals Show this location only Back to top
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The Victorian Secret - Just Steps from Theatres, Restaurants & Park
2BR/2BA
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Sleeps 4-6
– Ashland #62216
$200 - $250 per night 2 night min stay
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Idyllic House & Cottage W/ English Country Gardens - Groups Welcome
3BR+/2BA
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Sleeps 8-10
– Ashland #172702
From $145 - $250 $ US
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Lake Side Lodge Kids and Pets Welcome. Short Drive to Ashland
3BR+/2.5BA
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Sleeps 10-12
– Ashland #1792
$250/nt all taxes included
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Charming Country Retreat, Minutes to Ashland!
2BR+/2.5BA
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Sleeps 8
– Ashland #345636
$200 per night 2 night min stay
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Location-Comfort-Luxury - Just Steps from Ashland's Plaza
5BR+/6BA
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Sleeps 2-16
– Ashland #152492
$85- $195/nt/unit
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Beautiful Turn-of-the-Century Farmhouse on Working Horse Ranch
4BR+/5BA
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Sleeps 1-16
– Ashland #44014
$325 per night 2 night min stay
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Beautifully Remodeled 2 Blocks from Theater and Town!
1BR+/1BA
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Sleeps 2-4
– Ashland #407195
$175 per night
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Abbott'S Cottages - Delightful Cottages - Close to Theatres
3BR+/2BA
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Sleeps 10
– Ashland #181789
$150- $250/nt
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Town Center -2 Modern Executive Townhomes with Full Security
2BR/2BA
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Sleeps 4
– Ashland #286244
$225- $325/nt
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Charming Craftsman House and Studio, 4/3, Close to Theatres
4BR+/3BA
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Sleeps 10-14
– Ashland #239720
From $200/nt
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Adorable, Immaculately Clean, Spacious & Comfortable 2 Bedroom
2BR+/1BA
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Sleeps 4-6
– Ashland #308963
$125 - $175 per night 2 night min stay
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Bad Taste *B -N- B*
3BR+/2BA
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Sleeps 8-10
– Ashland #38030
From $115/nt - $2200/mo
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Romantic Country Cottage with European Ambiance
1BR+/1BA
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Sleeps 3
– Ashland #305090
$165 per night 3 night min stay
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Delaunay House....One Block from Town and Shakespeare.
4BR+/4BA
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Sleeps 8-14
– Ashland #88337
$110 - $135 per night 2 night min stay
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The Perfect Vacation Cottage
2BR+/2BA
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Sleeps 6
– Ashland #175956
$225 - $275 per night 2 night min stay
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Artycottage... June 9-14 Not Booked 20% Off 4 Nights
1BR+/1.5BA
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Sleeps 4
– Ashland #205948
$150/nt - $975/wk
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Beautiful 1 Bed Apartment in Historic Home 3 Blocks to Downtown
1BR+/1BA
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Sleeps 2-4
– Ashland #289973
140.00 TO 160.00 PER NIGHT
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Beautiful Historical Home 2 Blocks from Theater and Plaza!
2BR+/1BA
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Sleeps 4-6
– Ashland #406820
$225 per night 2 night min stay
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Classic Victorian- Sleeps 2-8...a Short Stroll to the Theatres
3BR+/2.5BA
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Sleeps 8
– Ashland #302211
From $240/nt full house
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Best House to Visit Oregon Shakespeare Festival
4BR+/4BA
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Sleeps 10-12
– Ashland #89026
$350/nt
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Beautiful Garden Cottage in Downtown Ashland
2BR+/2BA
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Sleeps 5-8
– Ashland #252823
$3660 per month 30 night min stay
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Ist Class Reviews! Beautiful House, Peaceful Creekside Setting
2BR/2BA
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Sleeps 4
– Ashland #289543
250.00
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Asian Inspired Escape with View - Just 3 Miles from Downtown
4BR+/3BA
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Sleeps 8-12
– Ashland #318531
$400 per night 3 night min stay
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Frieda's House: 'Gorgeous Vintage Artist Home with Mt.Views '
4BR+/2.5BA
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Sleeps 6-12
– Ashland #176506
$2500 - $6000
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Stunning, Modern, up Scale House, Walk to Town
2BR+/1BA
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Sleeps 4
– Ashland #135974
$150.00
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Heaven and Earth - Luxury Mtn Retreat Villa
4BR+/3.5BA
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Sleeps 10-16
– Ashland #106758
$250-$450/nt- $2250/wk
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Charming Light Filled Home Close to Theatres
2BR+/1BA
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Sleeps 6-7
– Ashland #347557
$175 per night 2 night min stay
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Elegant Townhome Near Ashland's Shakespeare Theaters
3BR/2.5BA
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Sleeps 6
– Ashland #339655
From $2400 - $3000/mo.
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Meadow House ~a Sanctuary in the Heart of the Colestin Valley
3BR+/3BA
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Sleeps 8-12
– Ashland #374452
$130-$190/nt - $850- $1250/wk
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Sweet & Cheerful Studio, Short Walk to Shakespeare
Studio/0BA
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Sleeps 2-3
– Ashland #471639
$150 per night 2 night min stay
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A Zen-Like Getaway! Just Minutes to Ashland! Beautifully Appointed!
2BR/1BA
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Sleeps 4
– Ashland #368473
$125 - $150 per night 2 night min stay
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Stunning Studio, Italian Motif, Walk to Town
Studio/1BA
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Sleeps 0-2
– Ashland #368352
$99- $125.00
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Helman House-Three Blocks from the Oregon Shakespeare Festival
2BR/1.5BA
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Sleeps 5-6
– Ashland #151735
$150 - $250 per night 2 night min stay
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Charming Historic District Cottage
1BR+/1BA
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Sleeps 2-4
– Ashland #152162
From $150/nt - $850/wk - $2700/mo
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New Listing 'Cabin in the Tree Tops'
4BR+/4BA
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Sleeps 10-12
– Ashland #440724
$425 per night 3 night min stay
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Quiet, Peaceful, Family or Romantic Getaway, Ashland
2BR+/1BA
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Sleeps 7
– Ashland #326005
$175 per night 2 night min stay
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2nd Street Cottages -- Just Steps from Theaters & Downtown
4BR+/3BA
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Sleeps 8-14
– Ashland #402580
From $220- $420/nt
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Ashland's Favorite Family Lodging, 1 Block to Theaters!
8BR+/6BA
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Sleeps 31
– Ashland #442846
$824 - $1030 per night 1 night min stay
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Little Creek Ranch Cottage & Garden Studio - Groups Welcomed
4BR+/2BA
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Sleeps 5-9
– Ashland #303654
$100 - $165/nt ( $700 - $990/wk)
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Location, Comfort and Charm - the Perfect Combination
2BR/2BA
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Sleeps 4
– Ashland #418679
$1800 per month Oct - April
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Private & Affordable Retreat with Magical Views
1BR/1BA
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Sleeps 2
– Ashland #409677
$125 per night, $750 per week
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Cabin#14 on Beautiful Hyatt Lake. Mountain Views Near Ashland.
1BR+/1BA
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Sleeps 2-6
– Ashland #360787
$169-$209/nt, $850/wk
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'Garden Cottage in the Historic District' - Walk Downtown!
3BR+/2BA
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Sleeps 3-6
– Ashland #187079
$3,500/mo
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Best View in Ashland! Vacation Rental or Month to Month.
2BR/2BA
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Sleeps 4
– Ashland #345741
$1250.00/ $1700.00 a mo
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Luxurious Home with Expansive Views on 6 Private Acres...
6BR+/4.5BA
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Sleeps 10
– Ashland #340422
From $375/nt
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Studio House Close to Downtown Plaza
1BR/1BA
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Sleeps 3
– Ashland #457370
$85 - $105 per night 2 night min stay
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Oak Hideaway - Handicap Accessible Vacation Cottage, Downtown Ashland
2BR+/1BA
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Sleeps 6
– Ashland #447574
$185 - $230 per night 1 night min stay
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Quiet Comfortable Country Home Five Minutes from Shakespeare
4BR+/2BA
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Sleeps 7-8
– Ashland #303158
$200- $350 per night.
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The Cypress House a Main St. Home ~ Walk to Theaters & More...
3BR+/2BA
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Sleeps 6
– Ashland #406005
1850- 3500
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The Lavender Country Estate in Charming Ashland Oregon
4BR/3BA
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Sleeps 8-10
– Ashland #54028
$600/nt - $4,000/wk - $13,000/mo
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Stone's Throw Bungalow ~ Charming Craftsman, Walk to Plays, Licensed
1BR/1BA
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Sleeps 1-2
– Ashland #254791
$100 - $125 per night 2 night min stay
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Walk to Town from This Charming and Updated Cottage.
2BR+/2BA
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Sleeps 6
– Ashland #422587
$100 - $200 per night 2 night min stay
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Peaceful Garden Setting - Downtown - Sleeps 6..Love Kids
3BR/2BA
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Sleeps 7
– Ashland #203556
$150 - $250
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Beautiful and Well Appointed Home, Spacious and Immaculate!
2BR+/2.5BA
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Sleeps 8
– Ashland #409870
$225 - $275 per night 2 night min stay
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Terra Cottage Inn - Ashland, Oregon
2BR/1BA
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Sleeps 4
– Ashland #65608
$320/2nt - $875/wk - $2850/mo
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High Street Cottage Artists' Garden Cottage Clean & Perfect
2BR/1BA
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Sleeps 4
– Ashland #114242
From $335/2nt - $975/wk - $3200/mo
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Cozy Guesthouse Steps Away from Downtown Ashland/Shakespeare
2BR+/1BA
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Sleeps 4-6
– Ashland #395392
$150 - $200 per night 2 night min stay
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Large Family Dream Home - 5 Miles from Ashland's Shakespeare
4BR+/3.5BA
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Sleeps 11-12
– Ashland #391850
$400 per night 2 night min stay
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'Sweet Little Garden Studio'
1BR+/1BA
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Sleeps 2
– Ashland #344663
$65nt - $390
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Large Craftsman.Views. Outdoor Space. 10 Min to Town & Theatre
5BR/2.5BA
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Sleeps 11-12
– Ashland #402058
$300- 375/nt
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A Remote, Private Retreat But Centrally Located, 2 Mi from Lithia Park
3BR/3BA
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Sleeps 8-12
– Ashland #458734
$400 per night 2 night min stay
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The Victorian Cottage
3BR/2BA
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Sleeps 4-6
– Ashland #173490
$2,500 per month
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New Chalet 15 Minutes from Ashland!
3BR/2.5BA
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Sleeps 6-10
– Ashland #263887
$225/nt - $1200/wk (low)
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Spectacular Views! Private Jacuzzi, Wifi, 52' Hdtv
3BR/2BA
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Sleeps 8
– Ashland #327146
$225/nt
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Getaway in the Trees, Walking Distance to Town
1BR/1BA
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Sleeps 2
– Ashland #354469
$110 per night 1 night min stay
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Shakespeare Lair
1BR/0BA
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Sleeps 2
– Ashland #445693
$1200 per month 30 night min stay
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Quan Yin Cottage
1BR+/1BA
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Sleeps 2
– Ashland #355736
$1250 per month 30 night min stay
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Beautiful Studio Cottage 2 Blocks from Downtown and Theaters
Studio+/1BA
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Sleeps 2-4
– Ashland #142767
$975/month
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Charming, Cozy Cottage, a Perfect Getaway Spot.
2BR/2BA
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Sleeps 4-6
– Ashland #449869
$200 per night 3 night min stay
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The Roost at Barking Raven Inn- Quiet, Private & Walk to Town
1BR/1BA
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Sleeps 2
– Ashland #395065
$120 - $175 per night 2 night min stay
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In the Heart of the Theater District
2BR/2.5BA
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Sleeps 4
– Ashland #373578
$300 per night 3 night min stay
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One Block to Theater, Park and Town -- Walk Everywhere!
1BR+/1BA
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Sleeps 1-4
– Ashland #454721
$1200 per month 30 night min stay
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Walk to Theatres in Ashland from This Charming Home
3BR+/1BA
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Sleeps 6-8
– Ashland #115319
$110- $195/nt
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Easy 10 Min. Walk to Plaza in Pristine Garden Setting! Monthly Rental
1BR+/1BA
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Sleeps 2-3
– Ashland #394913
1,400.00 per month
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La Dolce Vita 'the Sweet Life'
1BR/1BA
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Sleeps 2
– Ashland #147201
$149-$175nt - $900- $1050/wk
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Abigail's Cottage - 10 Minute Walk to Plaza & Theaters!
2BR/1.5BA
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Sleeps 6
– Ashland #462296
$225 per night 2 night min stay
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Beautiful Hyatt Lake - Camper's Cove Resort
2BR+/1BA
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Sleeps 6
– Ashland #295473
149/nt for 2 people + $10.00 per personj
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The Brenden House, Walk to Theaters
3BR+/2.5BA
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Sleeps 6-8
– Ashland #220743
$250 per night 2-4 night min stay
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Cottage Walking Distance Down Town Ashland! Month to Month
1BR+/1BA
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Sleeps 2-4
– Ashland #264300
$1300.00- $2000/mo
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Vacation Rental in Ashland, OR
3BR/2BA
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Sleeps 8-10
– Ashland #88151
$75- $175/nt
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Spring Special: 15% Off a Two-Night Stay
1BR+/1BA
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Sleeps 4
– Ashland #421751
$150 - $195 per night 2 night min stay
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Brand New Close to Downtown Small House
1BR/1BA
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Sleeps 1-2
– Ashland #114688
From $1200/mo
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3 Bedroom Flat in the Heart of Ashland
3BR+/2BA
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Sleeps 8
– Ashland #422568
from $150/night- $260/night $ US
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Stroll to Shakespeare - Carriage House Studio Apartment
1BR+/1BA
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Sleeps 2-3
– Ashland #431247
$125/night plus tax,2 night minimum
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Ashland/Talent - Unique Large Studio Apartment in the Country
1BR/1BA
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Sleeps 2
– Ashland #199225
$100/nt
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Stay on the Best Street in Ashland!
1BR+/1BA
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Sleeps 2-4
– Ashland #181670
From $1,000 to $1,200 a mo.
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Beautiful, New, Designer House
1BR+/1BA
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Sleeps 3-5
– Ashland #227652
$2600
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The Dogwood Suite at Tudor House Vacation Rentals
1BR/2BA
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Sleeps 3-4
– Ashland #446391
$99 - $159 per night 2 night min stay
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2 Bedroom Flat in the Heart of Ashland
2BR+/1BA
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Sleeps 5
– Ashland #426891
From $150/night- $260/night
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Fully Furnished Studio in Ashland, All Utlities Included!
Studio/1BA
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Sleeps 2
– Ashland #446186
$850 - $925 per month 30 night min stay
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Sheepcourt Retreat, Private House on an Acre, Near Park
1BR/1BA
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Sleeps 2
– Ashland #356136
$2800 a month
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The Greensprings Retreat - 20 Minutes to Downtown Ashland
3BR/2BA
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Sleeps 6-10
– Ashland #460863
$250 per night 2 night min stay
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Charming 3 BR/2 BA Ranchette with Views/ Privacy and No Tax!
3BR/2BA
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Sleeps 6-8
– Ashland #254423
$225/nt
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The Maple Apartment at Tudor House Vacation Rentals
2BR/2BA
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Sleeps 4
– Ashland #476319
$99 - $169 per night 2 night min stay
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Hanna's House- Your Home Away from Home,
1BR/1BA
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Sleeps 2
– Ashland #371879
From $130- 160/nt, 2 nt minimum
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Mountain Views. Walk to Town. Very Quiet - Dog Welcomed
1BR/1.5BA
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Sleeps 1-2
– Ashland #460704
$945 - $980 per week 7-14 night min stay
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Beautiful and Well Appointed Home, Spacious and Immaculately Clean!
2BR+/2.5BA
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Sleeps 8
– Ashland #983800ha
$225 - $275 per night 2 night min stay
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Exceptional Ashland Home
3BR/1BA
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Sleeps 5
– Ashland #205164ha
$1500 per month 30 night min stay
- Ashland Hot Springs Cottage with in-Room Mineral Bath 1BR/1BA – Sleeps 2 – Ashland #290258ha
- Helman House-Close to Restaurants, Shakespeare, & Lithia Park 2BR+/2BA – Sleeps 6 – Ashland #205590ha
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The Victorian Secret - Just Steps from Theatres, Restaurants & Park
2BR/2BA
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Sleeps 4-6
– Ashland #62216
Overview of Ashland Vacation Rentals
Ashland Vacation Rentals in South Oregon’s Rogue Valley
Southern Oregon’s fertile Rogue Valley was originally inhabited by the Rogue Indians and settled by pioneers around 1846. Visitors to Ashland vacation rentals will find it somewhat easier to get here nowadays. The region is serviced by Medford International Airport and by car is accessed from Interstate 5. The area has a mild climate with distinct seasons. The warm summers and good snow during the winter make it an ideal year-round vacation area.
Ashland Vacation Houses for Historic Towns
The town of Ashland is just 15 miles from the border with California at the southern end of this stunning valley. With its backdrop of the 7,500-foot high Mount Ashford and its setting in the foothills of the Siskiyou Mountains, Ashland makes a great vacation base. Ashland lodging offers a variety of outdoor activities with the benefits and convenience of a town. The town has charming neighborhoods with wide streets and a variety of parks and gardens. It is great place to relax and walk or bike around. The nearby town of Medford is renowned for its wineries and vineyards. Here, visitors can enjoy wandering the market to buy direct from the growers with specialties of jams and jellies, beautifully fresh vegetables, cheeses and fruits fresh from the orchards. To make the most of a vacation here, visitors will enjoy the many scenic routes to explore here. Among these is Grants Pass, an old river town where the pace of life remains a tranquil one. At the Rogue River Loop, visitors will find a loop of natural attractions, including the southern end of the Oregon Trail. A walking tour takes in sites like the area of the Rogue Indian Wars, the Grave Creek Covered Bridge and a stop at the historic Wolf Creek Inn.
Ashland Vacation Houses Are ideal for the Great Outdoors All Year-Round
Ashland vacation houses in this valley region are ideal to explore the valleys of South Umpqua and the Illinois Valley. South Umpqua is home to many historic old towns like Canyonville, Days Creek, Myrtle Creek, Riddle, and Tri City. Each is unique but all offer a chance to explore a rural way of life. There are various museums to discover as well as outdoor pursuits like fishing, boating, and hiking. The Illinois Valley is on route to the Wild Rivers Coastline of Oregon. One of Oregon’s best state parks is here, at Lake Selmac. Nearby, stop to view the meadows of carnivorous plants such as Cobra Lillies and spectacular wild flowers. Famous for its "Land of Umpqua," the city of Roseburg is a great place with many natural areas to discover. Here, two branches of the Umpqua River meet to form a glorious river. Visitors can experience whitewater rafting, explore the waterfalls, hike the trails by the river, and anglers can fish for salmon and steelhead. The Highway of the Waterfalls is a designated National Scenic Byway, filled with some of the most incredible waterfalls and nature trails leading to hidden away fishing holes. This area is perfect for winter activities such as downhill and cross country skiing and snowmobiling.
Ashland Lodging Includes Spacious Family Homes and Cozy Cabins
There is a wide variety of Ashland vacation houses around Mount Hood. Whether visitors require a spacious home for 15 or a cozy cabin for two with a hot tub, visitors will find a great place waiting here. Each home comes equipped with everything you need for a great vacation, including fully equipped kitchens, patios or decks with furniture and BBQs, and luxuries like wifi internet access and games areas. Some are waterfront properties; some are in the forests and some by the golf course. Wherever you want to be, the perfect place awaits you.