Cottage
10.0(236 Reviews)
1 Bedroom
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $288/Night
7 Nights - US $2,014
Ashland Holiday Rentals
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Compare Villas, Resorts, & Rentals in Ashland
10.0
House
10.0(4 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
View- Air Conditioner
US $961/Night
7 Nights - US $6,728
House
10.0(10 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $377/Night
7 Nights - US $2,642
House
10.0(171 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $302/Night
7 Nights - US $2,113
House
10.0(3 Reviews)
3 Bedrooms
8 Guests
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
US $287/Night
7 Nights - US $2,007
House
10.0(124 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $473/Night
7 Nights - US $3,309
House
10.0(108 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $300/Night
7 Nights - US $2,097
Apartment
10.0(106 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $179/Night
7 Nights - US $1,250
House
10.0(103 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $337/Night
7 Nights - US $2,362
Luxury Holiday Rentals in Ashland
Over 463+ Luxury Holiday Rentals in or Near Ashland
Apartment
10.0(1 Review)
8 Bedrooms
22 Guests
- Kitchen
- Air Conditioner
Child Friendly
TV
US $1,510/Night
7 Nights - US $10,569
Cabin
4 Bedrooms
14 Guests
- Kitchen
- Air Conditioner
Security/Safety
US $1,402/Night
7 Nights - US $9,813
Cabin
10.0(1 Review)
2 Bedrooms
8 Guests
- Kitchen
- Air Conditioner
- Child Friendly
- Security/Safety
US $1,219/Night
7 Nights - US $8,533
Hotel
10.0(1 Review)
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $1,198/Night
7 Nights - US $8,385
House
9.8(20 Reviews)
5 Bedrooms
14 Guests
Hot Tub- Parking
Ocean View- Balcony/Terrace
US $1,189/Night
7 Nights - US $8,320
Apartment
10.0(5 Reviews)
5 Bedrooms
14 Guests
- Kitchen
- Air Conditioner
- Security/Safety
US $1,077/Night
7 Nights - US $7,540
Apartment
10.0(7 Reviews)
8 Bedrooms
14 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $1,053/Night
7 Nights - US $7,370
Apartment
8.8(6 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,037/Night
7 Nights - US $7,262
House
10.0(1 Review)
5 Bedrooms
14 Guests
- Hot Tub
- Parking
Pool- Kitchen
US $1,019/Night
7 Nights - US $7,136
Top-Rated Holiday Rentals with a Pool in Ashland
Over 49+ The Best Private Villas and Holiday Rentals in Ashland with a Pool
House
10.0(36 Reviews)
3 Bedrooms
10 Guests
Private Pool- Hot Tub
- Pool
Spa
US $568/Night
7 Nights - US $3,979
Apartment
10.0(27 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $292/Night
7 Nights - US $2,046
House
10.0(19 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Pool
- Spa
US $728/Night
7 Nights - US $5,095
Hotel
10.0(3 Reviews)
- Parking
- Pool
- Air Conditioner
Internet
US $212/Night
7 Nights - US $1,485
House
10.0(2 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $733/Night
7 Nights - US $5,130
US $230/Night
7 Nights - US $1,610
US $207/Night
7 Nights - US $1,451
US $201/Night
7 Nights - US $1,405
Bed & Breakfast
9.8(42 Reviews)
1 Bedroom
Breakfast- Parking
- Pool
- Spa
US $336/Night
7 Nights - US $2,353
Pet-Friendly Holiday Rentals in Ashland
Over 177+ Pet-Friendly Holiday Rentals in or Near Ashland
Cottage
10.0(65 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $332/Night
7 Nights - US $2,323
Apartment
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $161/Night
7 Nights - US $1,127
US $408/Night
7 Nights - US $2,857
House
10.0(64 Reviews)
1 Bedroom
5 Guests
- Parking
- Spa
- Balcony/Terrace
- Kitchen
US $211/Night
7 Nights - US $1,474
House
10.0(1 Review)
5 Bedrooms
11 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $505/Night
7 Nights - US $3,533
Apartment
10.0(54 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $211/Night
7 Nights - US $1,480
House
10.0(18 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $216/Night
7 Nights - US $1,514
Cottage
10.0(13 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $245/Night
7 Nights - US $1,712
Apartment
10.0(12 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $265/Night
7 Nights - US $1,852
Large Holiday Rentals and Private Villas in Ashland
Over 44+ Large Holiday Rentals and Private Villas in or Near Ashland
House
9.4(9 Reviews)
2 Bedrooms
12 Guests
- Parking
- Spa
- Ocean View
- Balcony/Terrace
US $371/Night
7 Nights - US $2,600
Bed & Breakfast
9.9(26 Reviews)
7 Bedrooms
14 Guests
- Breakfast
- Parking
Skiing- Balcony/Terrace
US $235/Night
7 Nights - US $1,645
Villa
10.0(50 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $489/Night
7 Nights - US $3,424
House
9.6(17 Reviews)
8 Bedrooms
24 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Air Conditioner
US $1,017/Night
7 Nights - US $7,117
House
10.0(4 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $395/Night
7 Nights - US $2,767
Cabin
10.0(1 Review)
4 Bedrooms
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $591/Night
7 Nights - US $4,139
House
9.8(27 Reviews)
4 Bedrooms
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $564/Night
7 Nights - US $3,948
Villa
9.8(9 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $862/Night
7 Nights - US $6,035
House
9.6(85 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $624/Night
7 Nights - US $4,371
Wheelchair Accessible Holiday Homes in Ashland
Over 30+ Wheelchair Accessible Holiday Homes in or Near Ashland
Cottage
9.8(58 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $220/Night
7 Nights - US $1,543
Bed & Breakfast
9.1(123 Reviews)
6 Bedrooms
12 Guests
Oceanfront- EV Charge Station
- Parking
- Pool
US $180/Night
7 Nights - US $1,260
US $113/Night
7 Nights - US $788
Condo
5.0(4 Reviews)
1 Bedroom
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $335/Night
7 Nights - US $2,345
House
1 Bedroom
2 Guests
- Parking
- Kitchen
- Internet
Pet Friendly
US $152/Night
7 Nights - US $1,064
Condo
5.0(1 Review)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $810/Night
7 Nights - US $5,670
Condo
5.0(1 Review)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $275/Night
7 Nights - US $1,925
House
4.9(10 Reviews)
4 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $211/Night
7 Nights - US $1,477
House
4.7(39 Reviews)
6 Bedrooms
11 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $648/Night
7 Nights - US $4,536
Ashland Private Villas and Holiday Homes Under $200
Over 166+ Ashland Private Villas and Holiday Homes Under $200
US $136/Night
7 Nights - US $955
House
10.0(3 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Balcony/Terrace
- Child Friendly
Barbecue/Outdoor Cooking
US $174/Night
7 Nights - US $1,218
US $167/Night
7 Nights - US $1,171
House
10.0(9 Reviews)
2 Bedrooms
8 Guests
- Air Conditioner
- Internet
Laundry
Bedding/Linens
US $186/Night
7 Nights - US $1,304
Apartment
9.4(9 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Internet
US $181/Night
7 Nights - US $1,269
Apartment
10.0(7 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,390
Apartment
10.0(6 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $187/Night
7 Nights - US $1,308
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $84/Night
7 Nights - US $587
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Pet Friendly
US $123/Night
7 Nights - US $859
Instantly Bookable Holiday Homes in Ashland
Over 259+ Instantly Bookable Holiday Homes in or Near Ashland
House
10.0(94 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $503/Night
7 Nights - US $3,524
House
9.8(65 Reviews)
1 Bedroom
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $251/Night
7 Nights - US $1,756
House
10.0(43 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $229/Night
7 Nights - US $1,603
Cabin
10.0(15 Reviews)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Security/Safety
US $492/Night
7 Nights - US $3,443
House
10.0(11 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $274/Night
7 Nights - US $1,918
House
10.0(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $211/Night
7 Nights - US $1,479
House
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $362/Night
7 Nights - US $2,534
House
10.0(6 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $203/Night
7 Nights - US $1,421
House
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $476/Night
7 Nights - US $3,332
Book a Last Minute Place to Stay in Ashland
About Casai's Private Villas and Holiday Rentals in Ashland
Discover more than 472 vacation rentals available in Ashland. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Ashland.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Ashland, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Ashland. On average, places to stay near Ashland offer 663.7 ft², with nightly prices averaging US $302.
With Casai, finding and comparing holiday rentals in Ashland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Ashland, OR
There are 472 Ashland, OR Holiday Rentals
- Prices for a holiday home in Ashland start at US $59
- Top rated vacation home in Ashland is The Ashland Cottage, walk to town
- Most popular short term in Ashland is Stratford Inn
- Cheapest place to stay in Ashland is Timbers INN and Suites
- Most expensive holiday rental in Ashland is Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.
Frequently Asked Questions About Ashland?
What are the top holiday rentals in Ashland?
With numerous options available in Ashland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Ashland:
- The Ashland Cottage, walk to town
- Hanna`s House | Downtown Retreat, Steps to OSF
- The Perfect Vacation Cottage
- Custom Ashland Home with Fantastic Mountain Views
- Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall
- Beautiful little place. Walk to town and theaters!
- The Victorian Secret - Just Steps to Theaters, Plaza, Restaurants & Park. ENJOY!
- Premier Downstairs Flat in Perfect Down Town Location
- The Terra Cottage Inn - Ashland, Oregon
- High Street Cottage Artists' Garden Cottage Clean & Beautiful
How many holiday rentals have private pools in Ashland?
Discover a selection of holiday rentals with private pools near Ashland with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Ashland are best for families?
If you're searching for a family-friendly holiday home in Ashland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Ashland:
How many Casai.com holiday rentals are available in Ashland?
As of 2026, Casai boasts over 472 properties listed in the Ashland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Ashland.
Nearby Neighborhood (4)
| Neighborhood | Property Count |
|---|---|
| Historic Downtown District Vacation Rentals in Medford, Oregon | 190 |
| Historic Railroad District Vacation Rentals in Medford, Oregon | 50 |
| Siskiyou-Hargadine Historic District Vacation Rentals in Medford, Oregon | 25 |
| Skidmore Academy Historic District Vacation Rentals in Medford, Oregon | 322 |
