Ashland holiday homes

We found 282 holiday rentals — enter your dates for availability
Discover a selection of 108 homes, 56 apartments and other holiday rentals in Ashland that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a garden. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Ashland

Showing deals for:1 Jan - 8 Jan

Fire pit. Perfect for chilly nights.
Pool
Living room
Front of house
Exceptional
(38 reviews)

Come stay at our farmhouse! A place to integrate all the beauty surrounding you!

Ashland

8% off
NZ$10,791
for 7 nights, 1 room
NZ$1,542 per night
includes taxes & fees
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!
Kitchen
Kitchen
Winter scene
Exterior
Exceptional
(133 reviews)

Tranquil setting surrounded by panoramic mountain views, grazing horses

Phoenix

11% off
NZ$1,820
for 7 nights, 1 cottage
NZ$260 per night
includes taxes & fees
Tranquil setting surrounded by panoramic mountain views, grazing horses
Spacious front patio with fire pit & nice views of the mountains
Kitchen with new full size stainless steel appliances Coffee, teas or hot cocoa
Walkway between the two suites with a lock off door for your privacy if you want
Private kitchen
Exceptional
(49 reviews)

Ashland's Mountain View Vacation Rental.

Ashland

8% off
NZ$3,535
for 7 nights, 1 cottage
NZ$505 per night
includes taxes & fees
Ashland's Mountain View Vacation Rental.
Your friendly host(s) are often in the small cabin in case you need anything. :)
Dining
Living area
Living area
Exceptional
(9 reviews)

Gorgeous Lakeside BarnHOUSE + SAUNA!

Ashland

18% off
NZ$3,690
for 7 nights, 1 home
NZ$527 per night
includes taxes & fees
Gorgeous Lakeside BarnHOUSE + SAUNA!
Room
Private kitchen
Outdoor dining
Interior
Wonderful
(11 reviews)

Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!

Ashland

15% off
NZ$2,501
for 7 nights, 1 home
NZ$357 per night
includes taxes & fees
Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!
Exterior detail
Living area
Living area
Interior
Exceptional
(54 reviews)

East Main Downtown Bungalow

Ashland

15% off
NZ$2,031
for 7 nights, 1 home
NZ$290 per night
includes taxes & fees
East Main Downtown Bungalow
Interior
Exterior detail
Private kitchen
Interior
Exceptional
(5 reviews)

ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!

Ashland

12% off
NZ$1,850
for 7 nights, 1 cottage
NZ$264 per night
includes taxes & fees
ABBOTT'S COTTAGES- Cardinal cottage. 1 bedroom/1 bath, short walk to downtown!
Room
Property grounds
Private kitchen
Interior
Exceptional
(17 reviews)

Gorgeous custom Airstream with spectacular views only 4 mi. to Ashland

Talent

8% off
NZ$1,308
for 7 nights, 1 home
NZ$187 per night
includes taxes & fees
Gorgeous custom Airstream with spectacular views only 4 mi. to Ashland
Private kitchen
Property grounds
Exterior
Interior
Exceptional
(5 reviews)

ABBOTT'S COTTAGES- The Lark. 2 bedroom cottage, just two blocks to downtown

Ashland

8% off
NZ$3,295
for 7 nights, 1 cottage
NZ$471 per night
includes taxes & fees
ABBOTT'S COTTAGES- The Lark. 2 bedroom cottage, just two blocks to downtown
Private kitchen
Exterior
Outdoor dining
Living area
Exceptional
(10 reviews)

ABBOTT'S COTTAGES - Falcon. 2 bedroom/2 bath within walking distance to downtown

Ashland

8% off
NZ$3,572
for 7 nights, 1 home
NZ$510 per night
includes taxes & fees
ABBOTT'S COTTAGES - Falcon. 2 bedroom/2 bath within walking distance to downtown
Property grounds
Exterior
Titania kitchen - granite countertops, all the essentials, table can seat 4-6.
Living area
Exceptional
(87 reviews)

Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Ashland

8% off
NZ$2,646
for 7 nights, 1 apartment
NZ$378 per night
includes taxes & fees
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Room
Terrace/patio
Exterior detail
Private kitchen
Exceptional
(5 reviews)

ABBOTT'S COTTAGES, Avocet cottage- 3 bdrm/2bath, walking distance to downtown

Ashland

12% off
NZ$3,361
for 7 nights, 1 home
NZ$480 per night
includes taxes & fees
ABBOTT'S COTTAGES, Avocet cottage- 3 bdrm/2bath, walking distance to downtown
Interior
Private kitchen
Room
Dining
Exceptional
(8 reviews)

Galaxy-Themed, Fastest WiFi, 3 King Beds Home

Medford

6% off
NZ$3,598
for 7 nights, 1 home
NZ$514 per night
includes taxes & fees
Galaxy-Themed, Fastest WiFi, 3 King Beds Home
Private kitchen
Exterior detail
Room
Outdoor dining
Exceptional
(6 reviews)

ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown

Ashland

8% off
NZ$1,742
for 7 nights, 1 apartment
NZ$249 per night
includes taxes & fees
ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown
Living area
Exterior
Exterior detail
Private kitchen
Exceptional
(86 reviews)

Premier Downstairs Flat in Perfect Down Town Location

Ashland

16% off
NZ$3,572
for 7 nights, 1 home
NZ$510 per night
includes taxes & fees
Premier Downstairs Flat in Perfect Down Town Location
Titania kitchen
Oberon
Titania kitchen
Property grounds
Exceptional
(136 reviews)

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Ashland

7% off
NZ$2,135
for 7 nights, 1 apartment
NZ$305 per night
includes taxes & fees
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Private kitchen
Primary bedroom
Living area
Dining
Exceptional
(49 reviews)

New Downtown 3 Bedroom Upstairs Flat with views

Ashland

16% off
NZ$3,662
for 7 nights, 1 home
NZ$523 per night
includes taxes & fees
New Downtown 3 Bedroom Upstairs Flat with views

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The captivating area of Ashland awaits your stay

Enjoy the area's entertainment, theatre scene and opera with a rental holiday home in Ashland. Travellers to this welcoming city praise the festivals, gardens and cafes. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Ashland

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Ashland a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mount Ashland Ski Area (7.8 mi / 12.5 km)
  • EdenVale Winery (9.3 mi / 15 km)
  • Centennial Golf Club (9.4 mi / 15.1 km)
  • Rogue Valley Country Club (10.6 mi / 17.1 km)
  • Paschal Winery (5 mi / 8.1 km)
  • Rogue Creamery (16.3 mi / 26.2 km)

Exploring the gardens and other natural features in Ashland

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Ashland is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Lithia Park (0.5 mi / 0.9 km)
  • Emigrant Lake (6.3 mi / 10.2 km)
  • Hyatt Reservoir (12.9 mi / 20.8 km)
  • Howard Prairie Lake (16.1 mi / 26 km)
  • Lake of the Woods (28 mi / 45.1 km)
  • North Mountain Park (0.7 mi / 1.2 km)

Transport to and around Ashland

The nearest airport is in Medford, OR (MFR-Rogue Valley Intl.), located 14.4 mi (23.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Klamath Falls, OR (LMT-Klamath Falls Intl.), which is 49.7 mi (79.9 km) away.

Frequently asked questions

What is the best area to stay in Ashland when booking a holiday rental?
When considering a holiday rental in Ashland, Oregon, a popular area to stay is the downtown district. This vibrant neighbourhood is renowned for its charming atmosphere, with an array of boutique shops, delightful cafes, and restaurants serving up local cuisine. A highlight of this area is the Oregon Shakespeare Festival, which draws theatre enthusiasts from far and wide, offering a rich programme of performances throughout the year.Another appealing area is the Ashland Creek neighbourhood, which provides a more tranquil setting, ideal for nature lovers. Here, you can enjoy easy access to the stunning trails of Lithia Park, a beautiful expanse of greenery great for leisurely strolls or picnics. This park is also home to the beautiful Japanese Garden and a lovely duck pond, making it a fantastic spot for relaxation and outdoor activities.Both neighbourhoods have a variety of properties available, ranging from quaint cottages to modern apartments, ensuring that visitors can find accommodation that suits their needs and preferences.
Where are the best Ashland ski resort rentals?
For those looking for ski resort rentals near Ashland, the closest ski area is Mount Ashland, located just a short drive from the town. In Ashland itself, travellers can find a variety of accommodations, including charming lodges and cosy cabins that cater to both couples and families. Many of these properties come equipped with essential amenities such as fully stocked kitchens, comfortable living spaces, and often stunning views of the surrounding mountains.In addition to these lodgings, travellers can also explore nearby rental options in the scenic area of Talent, which is just a few miles from Ashland. Here, visitors can find properties that may feature spacious backyards, hot tubs, and easy access to hiking trails, superb for unwinding after a day on the slopes.Furthermore, Ashland is not just a ski destination; it is also renowned for its vibrant arts scene, particularly the Oregon Shakespeare Festival, which adds cultural richness to the area. Many accommodations in Ashland offer proximity to local shops and restaurants, ensuring a well-rounded experience for those looking to enjoy both winter sports and the local charm.
What is the most popular type of holiday rental accomodation in Ashland?
In Ashland, holiday houses are the most popular type of holiday rental, with approximately 352 available throughout the area. These properties are often situated in charming neighbourhoods close to the Oregon Shakespeare Festival and the beautiful Lithia Park, making them ideal for visitors wanting to explore the local culture and outdoor activities. Most holiday houses come equipped with spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation, superb for families or larger groups.Apartments also feature prominently, with around 200 options offering a more compact stay. These typically include essential amenities such as kitchen facilities, comfortable living areas, and sometimes balconies to enjoy the surrounding views. Cottages, numbering about 160, provide a quaint alternative with a homely feel, often set in serene locations that allow for a peaceful retreat.While cabins and chalets are less common, with around 72 cabins and several chalets available, they offer great experiences for those looking to immerse themselves in nature.
Are there any family house rentals in Ashland?
In Ashland, Oregon, there are a substantial number of family-friendly house rentals available, with around 87 options to choose from. This charming town is renowned for its vibrant arts scene and stunning natural surroundings, making it an excellent choice for family getaways. Properties in the area typically offer spacious living areas, fully equipped kitchens great for preparing family meals, and outdoor spaces where children can play and explore.Visitors can find homes in various neighbourhoods, such as the historic district, which is close to the renowned Oregon Shakespeare Festival, providing easy access to cultural performances and events. Additionally, many rentals are conveniently located near parks like Lithia Park, where families can enjoy picnics, hiking trails, and playgrounds.
Can I rent a holiday home with a pool or hot tub in Ashland?
In Ashland, there are several holiday homes available for rent that feature pools and hot tubs, with around 11 options to choose from. This picturesque town, known for its vibrant arts scene and proximity to the stunning Rogue Valley, offers a variety of neighbourhoods where these properties can be found. Many rentals are situated near the beautiful Lithia Park, providing a serene environment for relaxation.Travellers can expect a range of amenities in these holiday homes, including private pools, hot tubs for unwinding after a day of exploring, and spacious outdoor areas superb for gatherings. Fully equipped kitchens are common, allowing for self-catering, while some properties may also include features such as barbecue grills and fire pits, enhancing the outdoor living experience.
Are there pet-friendly house rentals in Ashland?
In Ashland, there are numerous pet-friendly house rentals available, with a variety of options suiting different tastes and preferences. Many of these holiday homes feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like patios or gardens where pets can enjoy some fresh air.The surrounding area is rich in cultural and natural attractions, making it a great destination for travellers with pets. Ashland is home to beautiful parks, including Lithia Park, which offers expansive green spaces, walking trails, and ponds that are superb for leisurely strolls with your furry companions. Additionally, the town is known for its vibrant arts scene, including the renowned Oregon Shakespeare Festival, providing visitors with plenty of entertainment options while enjoying a pet-friendly atmosphere.
Are there any remote work holiday rentals in Ashland?
In Ashland, Oregon, there are numerous remote work-friendly holiday rentals available, with around 648 options to choose from. This charming town is known for its vibrant arts scene and the famous Oregon Shakespeare Festival, making it an appealing destination for those looking to combine work and leisure. Many of the properties come equipped with essential amenities for remote work, such as reliable Wi-Fi access in both public areas and private rooms, ensuring that guests can stay connected while enjoying their surroundings.Travellers can expect to find a range of accommodations, from cosy cottages to spacious homes, often featuring comfortable workspaces, full kitchens for meal preparation, and inviting outdoor areas for relaxation. Ashland's picturesque landscape, including nearby hiking trails and the scenic Lithia Park, provides ample opportunities for breaks and outdoor activities after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Ashland?
In Ashland, popular rental amenities include kitchens, allowing guests to prepare their own meals, and onsite parking for convenience. Many properties also feature decks or patios, providing a pleasant outdoor space to relax and enjoy the surroundings. Additionally, a coffee and tea maker is commonly found in rentals, ensuring guests can easily brew their favourite hot beverages. For those travelling with pets, many accommodations in the area permit pets, making it easier for families to bring their furry companions along.
When is the best time to visit Ashland for a holiday rental?
The best time to visit Ashland for a holiday rental is during the summer months of June to August, with July being particularly popular. This peak season draws visitors eager to experience the vibrant setting of the Oregon Shakespeare Festival, which showcases an array of outstanding performances in a beautiful outdoor setting.With warm temperatures averaging around 25 to 30 degrees Celsius, summer in Ashland is superb for enjoying outdoor activities. The lush landscapes provide a stunning backdrop for hiking, exploring local parks, and participating in various festivals that celebrate the region's rich culture and community spirit.For those looking for a more budget-friendly option, consider planning your trip in December. Although it's the low season, the winter months offer a serene charm, with the possibility of light snowfall and festive holiday decorations throughout the town. This quieter time allows for a more relaxed exploration of Ashland's local art galleries, quaint shops, and delightful eateries.
What are the top attractions in Ashland?
In Ashland, visitors can engage in a vibrant cultural scene and stunning natural beauty. The Oregon Shakespeare Festival, located in the heart of the town, is a significant draw, showcasing a range of performances throughout the year, attracting theatre enthusiasts from all over. Nearby, Lithia Park offers a picturesque setting with its beautiful gardens, walking paths, and tranquil duck ponds, superb for leisurely strolls or picnics.The downtown area is filled with charming shops, cafés, and art galleries, allowing visitors to explore local crafts and enjoy a meal or coffee at one of the many inviting spots. For those interested in outdoor activities, the surrounding area provides opportunities for hiking, particularly in the nearby Cascade-Siskiyou National Monument, which boasts scenic trails and breathtaking views.
Are all fees included in the Ashland holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Ashland holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Ashland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Ashland holiday homes?
You can find great discounts on holiday homes in Ashland on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Ashland holiday home booking on Bookabach?
To find Ashland holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Ashland?
A long-stay holiday home in Ashland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Ashland holiday home?
Book your Ashland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Ashland?
Prices for holiday homes in Ashland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Ashland to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.