Search for vacation rentals in Ashland.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Ashland area to find the perfect spot for your vacay.

315 Maple St
	315 Maple St Ashland, OR $1,650 Vacation Rentals, Unknown 315 Maple St in Ashland is a 1 bedroom 1 bath house with a large fenced in back yard with large storage shed. Pets are negotiable upon owner approval. This home is across the street from the......

Holly St
	Holly St Ashland, OR $2,050 Vacation Rentals, Unknown Fantastic Location with Views Two bedroom one bath with craftsman features. Custom period details with modern updates. Sunroom-entry provides extra living space. Hardwood floors in entry-sunroom,......

Coffee Ln
	Coffee Ln Ashland, OR $1,800 Vacation Rentals, Unknown Adorable 2-bedroom, 1-bath cottage (built in 2023 with upscale finishes) in northern Ashland's 12-cottage West Village community on Coffee Lane. This all-electric, energy efficient home with......

449 Orchard St
	449 Orchard St Ashland, OR $1,350 Vacation Rentals, Unknown Nice, newly constructed modern styled cottage at rear of property. Located near Hann-Strawberry Park, and a mile from the Square. In quiet area at back of property, next to creek. Shared back yard......

300 Harrison St
	300 Harrison St Ashland, OR $2,150 Vacation Rentals, Unknown Great location - above the Boulevard, walk to downtown, Safeway. Appliances include refrigerator, stove. microwave, washer & dryer. Fenced-in backyard. Off-street parking & small building for......

9 Hillcrest St
	9 Hillcrest St Ashland, OR $3,420 Vacation Rentals, Unknown Beautifully restored and updated 1920s Craftsman. Close walk to Festival, Park, downtown. 4 Br, 3 Ba, office, bonus rm, laundry, 2 car garage, wood floors and carpeted bedrooms. Discount if no......

971 B St
	971 B St Ashland, OR $1,850 Vacation Rentals, Unknown Fully furnished two story one bedroom home in the railroad district of Ashland. Only 7 level blocks to downtown Ashland.This home has natural hardwood in the main living areas and carpet in the......

Almeda Dr
	Almeda Dr Ashland, OR $2,300 Vacation Rentals, Unknown Fully furnished in a newer Ashland neighborhood. Contemporary style and beautiful views. The hills to the north and Mt. Ashland to the south. Two bedrooms, two and a half baths. One bedroom is set......

272 N 1st St
	272 N 1st St Ashland, OR $1,250 Vacation Rentals, Unknown Tentatively available mid to late May. Updated photos coming soon! One cat is negotiable with excellent references and upon owner approval, with an additional security deposit of $500.00, and pet......

Sutton Pl
	Sutton Pl Ashland, OR $3,400 Vacation Rentals, Unknown Beautifully Appointed with Outstanding Views Located in The Oaks neighborhood of Ashland. Stunning views on three sides from the Cascades to Pilot Rock. Over three thousand square foot,......

236 1/2 N Mountain Ave
	236 1/2 N Mountain Ave Ashland, OR $1,150 Vacation Rentals, Unknown OWNER WILL PAY FOR ALL UTILITIES, INCLUDING INTERNET. SHARED YARD WITH THE OWNER/ COMMON AREA. SINGLE LEVEL DETACHED FROM THE MAIN HOME IS A STUDIO WITH A KITCHEN, BATHROOM, SPACIOUS ROOM/ DINING......

52 Alida St
	52 Alida St Ashland, OR $1,995 Vacation Rentals, Unknown Tentatively available mid-May. Darling, pet-friendly home; 1 to 2 small to medium pets negotiable upon owner approval, $25.00/monthly pet rent per pet, and an additional security deposit of $500.00......

Orchard St
	Orchard St Ashland, OR $1,350 Vacation Rentals, Unknown Nice, newly constructed modern styled cottage. Located near Hann-Strawberry Park, and a mile from the Square. In quiet area at back of property, next to creek. Shared back yard with owner. One......

220 4th St #3
	220 4th St #3 Ashland, OR $1,350 Vacation Rentals, Unknown If the property is not listed on our website then the property is no longer available. _____________________ DESCRIPTION: This downstairs apartment has been newly renovated. There is luxury vinyl......

88 Brooks Ln
	88 Brooks Ln Ashland, OR $2,200 Vacation Rentals, Unknown This light and bright 3 bedroom, 2.5 bath townhouse boasts a little over 1,600 sq. ft of living space. Open living room that leads to full kitchen with bar area that would be perfect for......

882 B St
	882 B St Ashland, OR $2,800 Vacation Rentals, Unknown New (built in 2022), one story, 3 bedroom, 2 bath home in Ashland's historic Railroad district. Open concept living, dining, kitchen. Custom built-in cabinets/storage in living/dining room. Quartz......

R1243 Greentree Way
	R1243 Greentree Way Ashland, OR $2,100 Vacation Rentals, Unknown Spacious 3 bedroom, 2 bath home, vaulted ceilings, large living room w/ ceiling fan, dining area, open kitchen with Range/Microwave/Dishwasher. Enjoy access to the patio from dining area, large......

674 Jaquelyn St
	674 Jaquelyn St Ashland, OR $2,500 Vacation Rentals, Unknown Introducing a charming 3-bedroom, 2-bathroom home in the desirable location of Ashland, OR. This lovely house features two bedrooms plus an office/bedroom, perfect for those who need a dedicated......

355 W Nevada St
	355 W Nevada St Ashland, OR $2,250 Vacation Rentals, Unknown Longing for elbow room or space to garden? This large mid-century split level home on almost a quarter acre has it! Four bedrooms, two bathrooms, living room with faux fireplace, upstairs bonus......

882 Plum Ridge Dr
	882 Plum Ridge Dr Ashland, OR $2,200 Vacation Rentals, Unknown 882 Plum Ridge Dr. is a 2 bedroom 2 bath 1,513 sq ft condominium in Mountain Meadows, Ashland's only 55+ community. This beautiful home includes a covered front porch entry, lots of windows for......

155 Ohio St
	155 Ohio St Ashland, OR $2,200 Vacation Rentals, Unknown Two bedroom two bath on Ohio Street. Quiet setting with established landscaping. Quality finishes with hardwood floors and two fireplaces that give great ambiance. Spacious kitchen with updated......

560 Weller Ln
	560 Weller Ln Ashland, OR $2,950 Vacation Rentals, Unknown Available now! Beautifully remodeled 3 bedroom (w/optional 4BR), 2.5 bath custom-built home on a tree-lined cul de sac in the Ashland hills. Awesome location less than one mile above the boulevard......

Park St
	Park St Ashland, OR $2,350 Vacation Rentals, Unknown Three bedroom, two bath home. Hardwood floors throughout the living room, dining, kitchen, and family room. Open floor plan. Large kitchen with expansive countertops. Stainless appliances. The main......

2880 Wedgewood Ln
	2880 Wedgewood Ln Ashland, OR $2,300 Vacation Rentals, Unknown Welcome to this charming 3 bedroom, 2 bathroom home located in the desirable Ashland, OR. This lovely property features a lockable custom-built work shed in the backyard with lighting and......

168 Lincoln St
	168 Lincoln St Ashland, OR $1,725 Vacation Rentals, Unknown Cute 2 bedroom, 1 bath house with wood fireplace in living room. There is also central heat and air. Large fenced backyard. Shed and shop detached. Covered front patio. Washer/Dryer hookups. Plenty......

131 Coolidge St
	131 Coolidge St Ashland, OR $1,900 Vacation Rentals, Unknown Cozy home in the beautiful town of Ashland above the boulevard! This charming 2 bed 1 bath property has a new mini split system with AC is perfect for someone looking to move to Ashland! Lovely......

Van Ness Ave
	Van Ness Ave Ashland, OR $1,795 Vacation Rentals, Unknown Sparkling clean 2 bedroom, 1 bath home, just a few blocks from Ashland plaza, located on a quiet alley. An incredible location that is steps to the old Briscoe School playground, Lithia Park,......

1250 1/2 Iowa St
	1250 1/2 Iowa St Ashland, OR $1,495 Vacation Rentals, Unknown Adorable open vaulted ceiling craftsmen cottage style house. Two bedroom one bath. Ceiling fans, Tankless Hot Water Heater, mini split HVAC. Short term rental, monthly, 1 pet appliances, couches if......

Oregon St
	Oregon St Ashland, OR $3,900 Vacation Rentals, Unknown "Above the boulevard" ! GATED upscale home close to SOU. Chef's kitchen with prep island & granite counters. Low VOC paint, wool carpet, spa like main bathroom. Hardwood floors in main living area.......

Harmony Cir
	Harmony Cir Ashland, OR $2,100 Vacation Rentals, Unknown Large 1,886 Sq. Ft. 3 bed/2 bath home with huge, garage-sized bonus room, plus 16x20 detached shop and 8x12 storage shed in quiet south Ashland neighborhood. Corner lot on cul-de-sac nearby shops,......

131 Ohio St
	131 Ohio St Ashland, OR $2,100 Vacation Rentals, Unknown Welcome to the Beautiful Furnished Cottage in downtown Ashland, Oregon! This charming 2-bedroom, 1-bathroom is the perfect place to call home. Located in the heart of Ashland, you'll have easy......

128 S Mountain Ave
	128 S Mountain Ave Ashland, OR $1,450 Vacation Rentals, Unknown Welcome to this charming 2-bedroom, 1-bathroom duplex located in the heart of Ashland, OR. This cozy home features hardwood floors throughout, adding a touch of warmth and elegance to the space.......

9 Nutley St
	9 Nutley St Ashland, OR $3,000 Vacation Rentals, Unknown Description Perfect for someone who appreciates the convenience of being downtown & the feeling of living in the woods, or for a couples retreat, writer's get away, thespian devotee refuge, outdoor......

Parkside Dr
	Parkside Dr Ashland, OR $3,000 Vacation Rentals, Unknown A unique well maintained home is available for rent as soon as April 9th.This three bedroom two bath is located less than 10 blocks from Lithia Park. A lush garden of trees, shrubs and flowers......

785 Pracht St
	785 Pracht St Ashland, OR $2,150 Vacation Rentals, Unknown Adorable single level 1940's cottage in a wonderful location. Step into this home and immediately feel the warmth and charm- from the original doug fir floors to the vintage Wedgewood range. The......

247 7th St
	247 7th St Ashland, OR $1,775 Vacation Rentals, Unknown Welcome to the charming Cute Cottage in the Railroad District of Ashland! This cozy 1 bedroom, 1 bathroom home features brand new washer/dryer, laminate flooring, a lovely patio for outdoor......

407 Harrison St
	407 Harrison St Ashland, OR $1,800 Vacation Rentals, Unknown Quiet studio cottage with sleeping loft 4 blocks from SOU, 4 blocks from downtown. Full kitchen, full bath with large soaking tub, large living room with high ceilings, loft bedroom, large screened......

Scenic Dr
	Scenic Dr Ashland, OR $2,750 Vacation Rentals, Unknown Clean, spacious, and comfortable home in Ashland, great, friendly neighborhood. Short walk to downtown. Three bedrooms two bathrooms, ~1300 sq. ft. with off street parking. Fully remodeled, new......

Patterson St
	Patterson St Ashland, OR $4,000 Vacation Rentals, Unknown This is a split level family home. Perfect for older children or elderly parents. Also, would be great for two couples or friends The top level has all amenities , dishwasher, washer and dryer, hot......

187 Harrison St
	187 Harrison St Ashland, OR $1,525 Vacation Rentals, Unknown This single level 1 bed/ 1 bath is close to town and SOU campus! This unit has been newly remodeled! High ceiling and all new kitchen cabinets and counters! There is a shared laundry room on-site......