Ashland vacation rentals

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Top-rated vacation rentals in Ashland

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Guest favorite

Apartment in Ashland

4.94 out of 5 average rating, 255 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 16 – 23

ﺩ.ﺇ459 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

Nov 9 – 16

ﺩ.ﺇ626 per night

Guest favorite

Cottage in Ashland

4.97 out of 5 average rating, 424 reviews

Victorian Garden Carriage House

You will wake in the trees, to the soft prospects of the forested Siskiyou mountains to the west. You'll discover enchanting views at every window, from city streets to a quiet English garden and pond. You are only a few steps from Ashland Plaza, yet the retreat-like environment we offer to all our guests requires that no incense, smoking, vaping or pets are allowed in the Carriage House. The City of Ashland has authorized the Carriage House. Our City Planning Action Number is PA-2013-01701.

Dec 11 – 18

ﺩ.ﺇ734 per night

Guest favorite

Tiny home in Shady Cove

4.95 out of 5 average rating, 198 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 30 – Oct 7

ﺩ.ﺇ553 per night

Guest favorite

Apartment in Ashland

4.97 out of 5 average rating, 115 reviews

Affordable Luxury- One block to Downtown

Welcome to The Matriarch, a historic heritage property in downtown Ashland. This self check-in style accommodations for our Suite 2, means you have the place all to yourself. Stroll to dinner at one of Ashland's finest restaurants or cozy up in the private outdoor living room. Expect thoughtful local touches and attention to every last detail. Soak in the beauty of bold design as you decompress in the large king bed. The Matriarch is our newest addition to the Swank House family.(#18-243)

Dec 3 – 10

ﺩ.ﺇ548 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 22 – 29

ﺩ.ﺇ388 per night

Guest favorite

Guesthouse in Ashland

4.98 out of 5 average rating, 507 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.

Dec 31 – Jan 7

ﺩ.ﺇ510 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

ﺩ.ﺇ442 per night

Guest favorite

Cabin in Ashland

4.94 out of 5 average rating, 224 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!

Aug 25 – Sep 1

ﺩ.ﺇ401 per night

Guest favorite

Camper/RV in Ashland

4.88 out of 5 average rating, 917 reviews

Cozy camping close to town

The 1973 Kit Companion is a 15-foot trailer converted to maximize space and guest experience. Featuring a water dispenser, French press, hot water kettle, lending library, and games; this adorable camper is both functional and gives guests a unique and comfortable space. The “Kit” is small, private, and located conveniently close to Ashland downtown and Interstate 5. Guests who stay in trailer have access to the shared bathroom and shower in the house.

Apr 30 – May 7

ﺩ.ﺇ203 per night

Guest favorite

Guesthouse in Ashland

4.9 out of 5 average rating, 337 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 16 – 23

ﺩ.ﺇ527 per night

Superhost

Guesthouse in Ashland

4.87 out of 5 average rating, 126 reviews

ABBOTT'S COTTAGES- Egret

A cozy hideaway for two tucked into a private corner, the Egret is a perfect place to come home to after enjoying a night at theatre or a walk in the park. Spanish tiles and hand forged iron accents add to the ambiance of this special studio cottage. There are other cottages on the property if you are with a group looking for more than one house. Just let us know!

Aug 9 – 16

ﺩ.ﺇ430 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

Nov 16 – 23

ﺩ.ﺇ846 per night

Guest favorite

Home in Ashland

4.96 out of 5 average rating, 240 reviews

Secluded Forest Log House 15 minutes to Ashland

Jul 22 – 29

ﺩ.ﺇ654 per night

Guest favorite

Home in Ashland

4.91 out of 5 average rating, 194 reviews

Ashland Haus Retreat - 1 block from downtown!

Nov 21 – 28

ﺩ.ﺇ765 per night

Superhost

Home in Ashland

4.95 out of 5 average rating, 107 reviews

Casa Bella

Nov 26 – Dec 3

ﺩ.ﺇ1,333 per night

Guest favorite

Home in Ashland

4.97 out of 5 average rating, 149 reviews

Terra Cottage Inn - Quintesential Ashland

Jan 28 – Feb 4

ﺩ.ﺇ641 per night

Superhost

Home in Grants Pass

4.79 out of 5 average rating, 247 reviews

Modern House in town with Hot Tub and fenced yard.

Feb 21 – 28

ﺩ.ﺇ368 per night

Guest favorite

Home in Grants Pass

4.93 out of 5 average rating, 175 reviews

Cedar Mountain Suite A -Home Theater, Gamer Ready!

Nov 23 – 30

ﺩ.ﺇ426 per night

Guest favorite

Home in Gold Hill

5.0 out of 5 average rating, 109 reviews

Hygge Hideaway. A home for rest and adventure

May 7 – 14

ﺩ.ﺇ524 per night

Show all

Other great vacation rentals in Ashland

Guest favorite

Yurt in Grants Pass

4.97 out of 5 average rating, 653 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

Feb 11 – 18

ﺩ.ﺇ370 per night

Guest favorite

Tiny home in Grants Pass

4.97 out of 5 average rating, 200 reviews

Tiny Cabin in the Woods w/ Hot Tub and Firepit

Feb 4 – 11

ﺩ.ﺇ455 per night

Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 703 reviews

BEE WELL Organic Spa Garden Studio

Aug 4 – 11

ﺩ.ﺇ372 per night

Guest favorite

Cottage in Medford

4.91 out of 5 average rating, 282 reviews

Stunning Private Orchard Property

Oct 4 – 11

ﺩ.ﺇ545 per night

Guest favorite

Guesthouse in Medford

4.97 out of 5 average rating, 231 reviews

Mel-Ohana: your favorite country retreat!

Sep 27 – Oct 4

ﺩ.ﺇ357 per night

Guest favorite

Apartment in Ashland

4.86 out of 5 average rating, 236 reviews

Winner 2023 Best of Ashland! Our Carriage House

Sep 28 – Oct 5

ﺩ.ﺇ685 per night

Guest favorite

Cottage in Ashland

4.99 out of 5 average rating, 143 reviews

The Red Dragon House

Nov 9 – 16

ﺩ.ﺇ708 per night

Guest favorite

Guesthouse in Ashland

4.97 out of 5 average rating, 143 reviews

Manzanita Cottage

Oct 6 – 13

ﺩ.ﺇ685 per night

Show all

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 guesthouse rentals in Ashland have wifi?
Absolutely! We offer over 30 guesthouse 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 cottage rentals in Ashland have a bbq area?
Absolutely! We offer over 10 cottage 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 30 homes with a bbq area, over 40 homes with self check-in, over 10 homes with a gym, over 90 homes with wifi, 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

Cottages

Houses

Apartments

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 Ashland

Home in Grants Pass

Home in Grants Pass

Home in Gold Hill

Other great vacation rentals in Ashland

Yurt in Grants Pass

Tiny home in Grants Pass

Guesthouse in Central Point

Cottage in Medford

Guesthouse in Medford

Apartment in Ashland

Cottage in Ashland

Guesthouse in Ashland

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 guesthouse rentals in Ashland have wifi?

Do house rentals in Ashland have a gym?

Do cottage rentals in Ashland have self check-in?

Do cottage rentals in Ashland have a bbq area?

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

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