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Check availability on Ashland Family-Friendly Hotels

Our top choices for Ashland family-friendly hotels

Games room
Callahan's Mountain Lodge

Callahan's Mountain Lodge

Callahan's Mountain Lodge
3.0 star property
Ashland
8.8 out of 10, Excellent, (1168)
"Beautiful place to stay "
United States
Daniel
The price is Rp1.707.880
Rp1.983.204 total
includes taxes & fees
16 Dec - 17 Dec
Callahan's Mountain Lodge
Winery
Lithia Springs Resort

Lithia Springs Resort

Lithia Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (1004)
"Lovely room with jacuzzi bath, cozy fireplace and comfy bed. Nice tea time snacks, and beautiful outdoor areas. Very dog friendly. "
United States
hannelie
The price is Rp1.564.038
Rp1.921.019 total
includes taxes & fees
14 Dec - 15 Dec
Lithia Springs Resort
Exterior
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
Ashland
8.8 out of 10, Excellent, (1001)
"Staff was excellent and very nice and room was clean and location is good Town is very cool 👍"
United States
Thomas
The price is Rp1.318.696
Rp1.338.476 total
includes taxes & fees
11 Jan - 12 Jan 2026
Comfort Inn & Suites Ashland
Garden
Ashland Springs Hotel

Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (1001)
"Charming historic hotel in downtown Ashland! Beautifully decorated, comfortable and well located. Restaurants and shopping galore. Theaters and playhouses all within a few blocks. We loved it!"
United States
Holly
The price is Rp1.449.645
Rp1.866.378 total
includes taxes & fees
17 Dec - 18 Dec
Ashland Springs Hotel
Lobby sitting area
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
Ashland
9.0 out of 10, Wonderful, (1497)
"A very great stay with our two dogs！"
United States
Yaolin
The price is Rp1.494.336
Rp1.853.123 total
includes taxes & fees
1 Jan - 2 Jan 2026
Ashland Hills Hotel & Suites
Lobby
The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western
2.5 star property
Historic Downtown District
8.6 out of 10, Excellent, (1005)
"The Bards Inn is lovely with each room themed after a Shakespe Play. Location is excellent just at the top of Main St. I can highly recommend this hotel"
United States
Suzanne
The price is Rp1.747.996
Rp1.949.015 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Bard's Inn, BW Signature Collection by Best Western
Outdoor dining
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
3.0 star property
Ashland
8.8 out of 10, Excellent, (1002)
"Staff was very helpful and kind. Room was very clean and location fit well for this trip."
United States
jennifer
Plaza Inn & Suites at Ashland Creek
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7)
"Great ~ memorable stay. "
United States
Melissa
The price is Rp2.052.452
Rp4.410.977 total
includes taxes & fees
2 Jan - 3 Jan 2026
Barclay Klum House by WanderLodges
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Family-friendly hotels with pools in Ashland

Standard Room, 2 Queen Beds, Non Smoking | Desk, blackout curtains, iron/ironing board, free WiFi
Cedarwood Inn of Ashland

Cedarwood Inn of Ashland

Cedarwood Inn of Ashland
2.0 star property
Ashland
7.4 out of 10, Good, (1002)
The price is Rp1.664.434
Rp1.855.863 total
includes taxes & fees
16 Dec - 17 Dec
Cedarwood Inn of Ashland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Stratford Inn

Stratford Inn

10/10 Excellent
"We had a great stay! Haven’t stayed here since 2001. Happy to report that the Stratford is in great shape and the staff is still friendly, knowledgeable, and super helpful."
Amy K 3-night trip
Posted 4 days ago
Stratford Inn

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Frequently asked questions

What's Ashland like for family-friendly holidays?
The welcoming destination of Ashland is a good choice if you've been considering a getaway with your children. The entertainment, festivals and hiking trails are just some of the things that make this an attractive spot for a family holiday. Take to the air and fly into Medford, OR (MFR-Rogue Valley Intl.), which is located 14.4 mi (23.3 km) from the city centre.
What's the best family accommodation in Ashland?
Lithia Springs Resort is a B&B with an outdoor pool and free parking, and it's a top choice on Expedia for families. Other good choices to stay with the children include Plaza Inn & Suites at Ashland Creek and Callahan's Mountain Lodge.
When's the best time to book a family-friendly holiday in Ashland?
The hottest months are usually August and July, with an average temperature of 18°C, while the coldest months are December and January, with an average of 3°C. Average annual precipitation for Ashland is 850 mm.
What's there to see and do with your family in Ashland?
While you and your family are visiting Ashland, you may want to explore some child-friendly attractions such as Allen Elizabethan Theatre, Thomas Theatre and Oregon Shakespeare Festival. Make sure that you have lots of time for activities such as Ashland Library and Mount Ashland Ski Area.