Ashland vacation rentals

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Top-rated vacation rentals in Ashland

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Guest favorite

Cottage in Ashland

4.96 out of 5 average rating, 364 reviews

Charming very well appointed cottage !

The Farm Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and updated for comfort & convenience. The cottage overlooks a pasture with 2 barns with the Siskiyous beyond to the south & the Ashland, Grizzly Peak Hills to the east. We are only 2 easy miles from downtown Ashland with multiple wineries close by. There is hiking, swimming at Emigrant Lake nearby as well. If quiet is what you are looking for, the cottage will meet all your needs.

Apr 8 – 15

G$25,392 GYD per night

Guest favorite

Apartment in Ashland

4.94 out of 5 average rating, 256 reviews

Mexico Apartment at Wood Hamlet, by Downtown

The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (low ceiling) Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Private parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Aug 4 – 11

G$26,072 GYD per night

Guest favorite

Guesthouse in Ashland

4.97 out of 5 average rating, 432 reviews

Charming cottage, walk to town.

Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown

Mar 4 – 11

G$35,502 GYD per night

Guest favorite

Tiny home in Shady Cove

4.95 out of 5 average rating, 199 reviews

Modern Tiny House w/ Hot Tub

Located on a hillside in Shady Cove. This is a spacious brand new 300 sq foot tiny home. The tiny house is located on our private property. We request for our guests to be respectful of our home, our neighbors, and surroundings. It is important that our guests treat the outdoor space as if they were camping and not leave any food outside as there is some wildlife in the area. Included is a covered gazebo with curtains on a private deck with a spa, and gas fire pit that also heats your legs.

Sep 28 – Oct 5

G$30,132 GYD per night

Guest favorite

Treehouse in Jacksonville

4.98 out of 5 average rating, 187 reviews

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

Oct 4 – 11

G$43,884 GYD per night

Guest favorite

Guesthouse in Ashland

4.94 out of 5 average rating, 106 reviews

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

Mar 15 – 22

G$22,024 GYD per night

Guest favorite

Guesthouse in Ashland

4.98 out of 5 average rating, 510 reviews

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

Oct 22 – 29

G$29,002 GYD per night

Guest favorite

Farm stay in Ashland

5.0 out of 5 average rating, 117 reviews

Kelly’s Carriage House 4 miles from Ashland

The Carriage House is located on Kelly's Farm four miles from the city of Ashland and less than two minutes from Highway 5. This two story home is 440 sq. ft with two sliding glass doors affording a 360 degree view of the mountains and sunset. There is an upstairs and downstairs deck, a propane grill and kitchen is fully furnished, two burners, countertop oven, and rice maker among other things. Set up for three people using two beds. Dogs are welcomed but we don't accept cats.

Aug 14 – 21

G$27,978 GYD per night

Guest favorite

Yurt in Grants Pass

4.97 out of 5 average rating, 654 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

NO CLEANING FEE! Large 24 ft yurt located on our 5 acre horse property. Gorgeous views to the west. Includes a king size bed, and queen sofa bed. Located in Applegate Valley. Many fabulous wineries nearby. We're 6 miles south of downtown Grants Pass, and 2 miles north of Murphy. Enjoy the hot tub under the stars, or catch a spectacular sunset. It's all good! Please note: ONLY well-behaved children are welcome. If your kids are destructive or abusive, you will be asked to leave.

Mar 30 – Apr 6

G$20,979 GYD per night

Guest favorite

Cabin in Ashland

4.93 out of 5 average rating, 226 reviews

Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil small studio cottage getaway. Our guest cabin has remodeled upgrades and is perfectly located minutes off the 5 freeway and just 3 miles from downtown Ashland's Shakepeare Fetival, Plaza shops, beautiful Lithia Park and Resturants. Venture to local lakes including Crater Lake, historic Jacksonville, and wineries in the pituresque Rogue Valley from our central location. Enjoy the privacy of our gated property with peaceful surroundings!

Nov 13 – 20

G$22,884 GYD per night

Guest favorite

Cabin in Grants Pass

4.98 out of 5 average rating, 413 reviews

The Cozy Cabin (with own private hot tub!)

Come relax and unwind in our cozy, peaceful cabin, tucked away in the beautiful hills of Grants Pass. With mountain views, stunning sunsets and a private wooded environment, it’s the perfect place to get away. Relax, read a good book, take a soak in the hot tub located just steps outside the master suite. The Cozy Cabin is filled with thoughtful touches, from throw blankets to high quality linens and towels, selected to create a welcoming and comfortable atmosphere.

Aug 14 – 21

G$28,977 GYD per night

Guest favorite

Guesthouse in Ashland

4.9 out of 5 average rating, 339 reviews

Private Garden Cottage w Sauna in RR District

Located in the historic Railroad District, our cottage is walking distance from the Shakespeare theater and all the trimmings of downtown. Walk to an award winning coffee shop down the alley and two grocery stores and park. Set between the cottage and our house are beautiful vegetable and flower gardens. There is a great deck for morning coffee and secure bike storage available. Miles of mountain hiking trails are close by. This will be your new spot!

Jan 4 – 11

G$29,843 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Ashland vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Ashland's top sights

Lithia Park198 locals recommend

Oregon Shakespeare Festival267 locals recommend

Ashland Springs Hotel3 locals recommend

Ashland's Own Shop'n Kart38 locals recommend

Brickroom76 locals recommend

Oregon Cabaret Theatre50 locals recommend

Other great vacation rentals in Ashland

Guest favorite

Home in Ashland

4.95 out of 5 average rating, 180 reviews

Coyote Moon

Mar 15 – 22

G$48,033 GYD per night

Guest favorite

Home in Ashland

4.96 out of 5 average rating, 241 reviews

Secluded Forest Log House 15 minutes to Ashland

Aug 23 – 30

G$37,140 GYD per night

Guest favorite

Home in Ashland

4.97 out of 5 average rating, 149 reviews

Terra Cottage Inn - Quintesential Ashland

Nov 1 – 8

G$36,398 GYD per night

Guest favorite

Home in Ashland

4.91 out of 5 average rating, 195 reviews

Ashland Haus Retreat - 1 block from downtown!

Apr 3 – 10

G$43,437 GYD per night

Guest favorite

Home in Grants Pass

4.93 out of 5 average rating, 177 reviews

Cedar Mountain Suite A -Home Theater, Gamer Ready!

Jan 24 – 31

G$21,751 GYD per night

Guest favorite

Home in Ashland

4.95 out of 5 average rating, 107 reviews

Casa Bella

Oct 30 – Nov 6

G$75,660 GYD per night

Guest favorite

Home in Grants Pass

4.98 out of 5 average rating, 143 reviews

Mid Century Modern 2 Bedroom, Walk to Downtown

Sep 21 – 28

G$20,079 GYD per night

Superhost

Home in Grants Pass

4.81 out of 5 average rating, 334 reviews

Modern Studio in the Heart of Grants Pass

Sep 25 – Oct 2

G$14,796 GYD per night

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Other great vacation rentals in Ashland

Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 705 reviews

BEE WELL Organic Spa Garden Studio

Oct 11 – 18

G$18,959 GYD per night

Guest favorite

Guesthouse in Central Point

4.97 out of 5 average rating, 886 reviews

The West Wing Guest House

Jun 30 – Jul 7

G$15,375 GYD per night

Guest favorite

Cottage in Ashland

4.97 out of 5 average rating, 424 reviews

Victorian Garden Carriage House

Dec 19 – 26

G$44,361 GYD per night

Guest favorite

Guesthouse in Ashland

4.95 out of 5 average rating, 314 reviews

Comfortable, Private Guest Lodging

Jul 13 – 20

G$34,371 GYD per night

Guest favorite

Guesthouse in Medford

4.95 out of 5 average rating, 166 reviews

Modern, pet-friendly, private - EV charger level 2

Dec 11 – 18

G$21,311 GYD per night

Guest favorite

Guesthouse in Medford

4.97 out of 5 average rating, 232 reviews

Mel-Ohana: your favorite country retreat!

Jun 28 – Jul 5

G$23,044 GYD per night

Superhost

Cottage in Ashland

4.78 out of 5 average rating, 291 reviews

Oak Street Studio

Feb 5 – 12

G$30,456 GYD per night

Guest favorite

Yurt in Eagle Point

4.97 out of 5 average rating, 216 reviews

Starlight Meadow Yurt

Aug 29 – Sep 5

G$26,769 GYD per night

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Quick stats about vacation rentals in Ashland

Total rentals
280 properties
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
100 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
19K reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Ashland?
Yes! Work meets play with ease at over 140 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Ashland?
Four-legged friends are welcome in Ashland. Choose from more than 100 vacation rentals for guests traveling with pets.
Are there Ashland vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Ashland, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in Ashland?
Ashland has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in private suite rentals in Ashland?
Experience the best of Ashland with our private suite rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Ashland have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ashland have a gym?
Absolutely! We offer over 10 house rentals with a gym in Ashland. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Ashland have self check-in?
Absolutely! We offer over 10 cottage rentals with self check-in in Ashland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ashland have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Ashland. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Ashland?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with self check-in, over 30 homes with a bbq area, over 90 homes with wifi, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Ashland vacation rentals

Top-rated vacation rentals in Ashland

Vacation rentals for every style

Apartments

Cabins

Cottages

Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

Other great vacation rentals in Ashland

Home in Ashland

Home in Ashland

Home in Ashland

Home in Ashland

Home in Grants Pass

Home in Ashland

Home in Grants Pass

Home in Grants Pass

Other great vacation rentals in Ashland

Guesthouse in Central Point

Guesthouse in Central Point

Cottage in Ashland

Guesthouse in Ashland

Guesthouse in Medford

Guesthouse in Medford

Cottage in Ashland

Yurt in Eagle Point

Quick stats about vacation rentals in Ashland

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Ashland?

Are there pet-friendly vacation rentals in Ashland?

Are there Ashland vacation rentals on Airbnb with pools?

Are there family-friendly vacation rentals in Ashland?

How much does it cost to stay in private suite rentals in Ashland?

Do apartment rentals in Ashland have wifi?

Do house rentals in Ashland have a gym?

Do cottage rentals in Ashland have self check-in?

Do house rentals in Ashland have a bbq area?

What are the most popular amenities for House Rentals in Ashland?

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