25 Best Ashland Apartments on Holiday Lettings - Vacation rentals

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27 Vacation rentals

24

Vacation cottage in Ashland

Oregon / Ashland

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about children
  • Air conditioning
Cottage, 1 bedroom, 1 bath (Sleeps 2) Country cottage above detached garage less than 10 minutes from downtown but feels like it’s far from the madding crowd. Hiking and biking right out your door. This 500+ sq. ft., new, fully furnished, self-contained, one bedroo …see more

from $145 / night

$950 / week

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from $145 / night

11

Vacation home in Ashland

Oregon / Ashland

3 10 2 nights min

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
Meadow House, built in 2000, features natural wood and plaster throughout, a well-stocked cook's kitchen with fresh eggs and milk in the refrigerator, and the quiet of off-grid living. The three bedroom, two bath house sleeps up to ten comfortably with 3 twin beds in t …see more

from $295 / night

$1859 - $2559 / week

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from $295 / night

7

Ashland Vacation apartment rental

Oregon / Ashland

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated crafts …see more

from $300 / night

$1900 / week

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Responds fast!
avg. 3 hours 58 minutes

from $300 / night

23

Ashland Vacation studio rental

Oregon / Ashland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Private garden
Just a stone's throw to the plaza, a licensed one-bedroom vacation rental suite is tucked behind one of Ashland's charming craftsman-style bungalows. Your private gated entrance, located behind the house, opens onto a peaceful garden and quaint patio - a wonderful place …see more

from $135 / night

$825 / week

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Responds fast!
avg. 3 hours 51 minutes

from $135 / night

(7) Excellent 

9

Vacation log cabin in Ashland

Oregon / Ashland

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
A “lake cabin” vacation can become a reality at Hyatt Lake Resort, approximately 22 miles east of Ashland on Rt. 66. The forest surrounds the cabin, which is located at “Campers’ Cove.” From the front deck you can BBQ while viewing the lake, enjoy the Jacuzzi or just …see more

from $149 / night

$895 - $1175 / week

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from $149 / night

(3) Very Good 

23

Vacation apartment rental

Oregon / Ashland

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Private cottage apartment with full kitchen and living area adjacent to family home. Covered porch and garden area to enjoy. Less than 15 minutes to Shakespeare Festival and downtown Ashland. Fresh eggs, local bread, jam, 1/2 and 1/2, milk and butter are stocked in fri …see more

from $100 / night

$600 / week

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from $100 / night

(21) Excellent 

15

Vacation log cabin with tennis court in Ashland

Oregon / Ashland

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
Beautiful log cabin in the Southern Oregon Cascade Mountains. Located very privately on 160 acres of mountain meadowland. Cabin sleeps up to 6 people, but the only door is on the downstairs bath with sleeping beds in the open loft and also downstairs. Full kitchen, f …see more

from $180 / night

$1100 - $1800 / week

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from $180 / night

(2) Excellent 

12

Ashland Vacation cottage rental

Oregon / Ashland

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street park …see more

from $175 / night

$1295 - $1575 / week

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from $175 / night

(7) Excellent 

20

Vacation cottage in Ashland

Oregon / Ashland

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Abigail's Cottage within walking distance to the city center, is licensed by the city of Ashland (Business License #007411 & Planning Action #06-275) and Jackson County, (#1581566C) and meets required health, safety and fire codes. Comfortable two bedroom 1 1/2 bath c …see more

from $185 / night

$1295 - $2345 / week

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Responds fast!
avg. 3 hours 5 minutes

from $185 / night

(2) Very Good 

15

Ashland Vacation cottage rental

Oregon / Ashland

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street park …see more

from $175 / night

$1295 - $1575 / week

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from $175 / night

7

Vacation apartment rental

Oregon / Ashland

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated c …see more

from $195 / night

$1200 / week

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Responds fast!
avg. 3 hours 58 minutes

from $195 / night

(1) Excellent 

31

Vacation home in Ashland

Oregon / Ashland

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Have a truly memorable trip to Oregon when you stay at this gorgeous 4-bedroom, 3-bathroom Ashland home, which sleeps 13. Enjoy the best of outdoor living with a private fishing pond and plenty of patio space with spectacular views! This Ashland vacation rental home is …see more

from $375 / night

$2394 - $2625 / week

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from $375 / night

9

Cottage rental in Ashland

Oregon / Ashland

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
We are located in the heart of Ashland. Only 2 blocks from Downtown. Enjoy the open Garden and Great location to all Restaurants, Shops, Theaters and Local Sporting Events. We are 3 blocks from University of Southern Oregon. Full Kitchen, Bedroom/Queen, Wall mounted r …see more

from $84 / night

$584 / week

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from $84 / night

21

Home rental in Ashland

Oregon / Ashland

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Beautiful, historic, fully renovated home with four bedrooms, three full baths and a fabulous welcoming front porch. Can be rented with Garden Suite, a 2 bedroom, 2 full bath house that sleeps five. Perfect location for your visit to Ashland. Historic Railroad Distri …see more

from $420 / night

$2940 / week

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Responds fast!
avg. 2 hours 3 minutes

from $420 / night

8

Ashland Vacation cottage rental

Oregon / Ashland

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Private garden
Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half a mile from theaters, Plaza and Downtown. Let this charming, historic home fill you with a sense of well-being and luxury. There are two bedrooms, …see more

from $195 / night

$1200 / week

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Responds fast!
avg. 2 hours 58 minutes

from $195 / night

(10) Excellent 

10

Vacation cottage in Ashland

Oregon / Ashland

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Ask about children
  • Air conditioning
Nestled into one of Ashland's best neighborhoods, the Terra Cottage Inn is a clean and beautiful, hand-crafted artists' cottage. Full of art, hand thrown pottery, custom built furniture and all the amenities to make this a true luxury experience. Quality comfortable b …see more

from $160 / night

$875 / week

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Responds fast!
avg. 1 hour 11 minutes

from $160 / night

(6) Excellent 

10

Ashland Vacation cottage rental

Oregon / Ashland

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Ask about children
  • Air conditioning
Set in Ashland's best neighborhood, this 1931 cottage has been lovingly restored and set up to address your every need. Cozy and incredibly clean, filled with art, hand-made pottery, antiques and hand crafted furniture. Comfortable beds, high quality linens and a fully …see more

from $165 / night

$975 / week

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Responds fast!
avg. 1 hour 11 minutes

from $165 / night

9

Ski studio to rent in Ashland

Oregon / Ashland

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Ski
  • Air conditioning
  • Private garden
Our property is located in the quaint Shakespearean town of Ashland, Oregon. The town has exceptional and award winning contemporary plays and the largest Shakespearean theater in the United States. We offer boating, hiking trails throughout the area. We hav …see more

from $150 / night

$950 - $1125 / week

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Responds fast!
avg. 44 minutes

from $150 / night

14

Vacation home in Ashland

Oregon / Ashland

3 9 2 nights min

  • 3 bedrooms
  • Sleeps 9
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Private garden
Welcome to the Blue Hyacinth in Blossom View Cottages. Walk to downtown and OSF or sit back and relax at the Blue Hyacinth, part of Blossom View Cottages. This is a luxurious and comfortable home in Ashland's historic railroad district. Downtown Ashland, the theaters, a …see more

from $285 / night

$1750 - $2100 / week

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Responds fast!
avg. 2 hours 58 minutes

from $285 / night

6

Vacation home in Ashland

Oregon / Ashland

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
STAY Overlooking beautiful meadows, the light filled studio sleeps up to six with two queen beds in the loft rooms and a double sofa-bed downstairs. The Farrmhouse Studio also features a wood stove and a full kitchen stocked with dry goods. On-Farm Store has all our …see more

from $200 / night

$1260 - $1610 / week

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from $200 / night

(2) Excellent 

25

Ashland Vacation cottage rental

Oregon / Ashland

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Fully restored vintage cottage in a quiet neighborhood just steps away from downtown Ashland and the theater. Surrounded by lovely gardens assuring a private and serene environment. The cottage is tastefully decorated , is immaculate and has 2 bedrooms, 2 baths, offi …see more

from $285 / night

$1925 / week

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from $285 / night

(1)  

17

Vacation farmhouse in Ashland

Oregon / Ashland

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Wonderful Craftsman-style FARMHOUSE built in 1912 and BUNKHOUSE on a working horse ranch just 3 minutes from downtown Ashland, home of the renowned Shakespeare festival and Britt festivals in nearby historic Jacksonville. 'FARMHOUSE' has 4 bedrooms and 2 full bat …see more

from $325 / night

$1950 - $2475 / week

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from $325 / night

18

Vacation home in Ashland

Oregon / Ashland

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Car not necessary
  • Air conditioning
  • Private garden
Our cottage is where you want to stay in Ashland! From its fantastic location to its custom craftsman design to the overall comfort, you'll be delighted with your choice! Just 3 level blocks from the downtown Ashland Plaza and Shakespeare festival. Along with clean, …see more

from $120 / night

$1000 - $1600 / week

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from $120 / night

10

Vacation home in Ashland

Oregon / Ashland

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Air conditioning
  • Private garden
This is a very beautiful modern unique property. Two bedrooms, sitting room/kitchenette all custom designed, Italian fixtures, exquisite cherry wood floors, marble bathroom, wireless internet, cable TV, HBO/ Showtime, central air/heater, and a stunning view of the pr …see more

from $200 / night

$1200 - $1550 / week

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Responds fast!
avg. 44 minutes

from $200 / night

(5) Excellent 

11

Ashland Vacation cottage rental

Oregon / Ashland

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
THE GARDEN SUITE IS A CHARMING TWO BEDROOM, 2 FULL BATH COTTAGE THAT COMFORTABLY WELCOMES 5 GUESTS. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great …see more

from $240 / night

$1680 / week

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from $240 / night

20

Vacation home in Ashland

Oregon / Ashland

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Pet friendly
This house is located on our ranch. It is 5 miles from downtown Ashland. It is 3 miles to local airport & 3.5 miles to local golf course. The views of the mountains, pastures, wildlife, cows & horses are very beautiful. It is relaxing and enjoyable. This home has har …see more

from $300 / night

$2000 / week

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from $300 / night

(5) Excellent 

16

Ashland Vacation cottage rental

Oregon / Ashland

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
THE HERITAGE SUITE IS A DELIGHTFUL 4 BEDROOM, 3 FULL BATH COTTAGE THAT ACCOMMODATES 8 GUESTS COMFORTABLY. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with …see more

from $420 / night

$2940 / week

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from $420 / night

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