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Check availability on Ashland Family Hotels

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov

Our top choices for Ashland family-friendly hotels

A modern bathroom with a bathtub, shower, and a small window with curtains.

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is AED 454
AED 977 total
includes taxes & fees
3 Nov - 4 Nov
Barclay Klum House by WanderLodges
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

2. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (6 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
The price is AED 376
AED 702 total
includes taxes & fees
3 Nov - 4 Nov
Hanna's House by WanderLodges
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

3. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is AED 572
AED 1,170 total
includes taxes & fees
30 Nov - 1 Dec
The Mountain Ave House by WanderLodges
A deck with a fire pit, outdoor seating, and a view of the countryside.

4. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Stunning views!! A+++ Experience!!"
United States
Jose
The price is AED 580
AED 1,330 total
includes taxes & fees
2 Dec - 3 Dec
Grandview of Ashland
A garden pathway with wisteria and red flowers, surrounded by lush greenery.

5. Arden Forest Inn

Arden Forest Inn
4.0 star property
Ashland
9.8 out of 10, Exceptional, (115 reviews)
"Tasteful charming bedroom and bathroom."
United States
Jean
The price is AED 502
AED 560 total
includes taxes & fees
2 Nov - 3 Nov
Arden Forest Inn
A large, two-story house with a wrap-around porch and a steeply pitched roof.

6. Winchester Inn

Winchester Inn
3.5 star property
Historic Downtown District
9.6 out of 10, Exceptional, (291 reviews)
"Amazing breakfasts, friendly staff, best location"
United States
Ellen
The price is AED 491
AED 606 total
includes taxes & fees
16 Nov - 17 Nov
Winchester Inn
A two-story building with a wooden facade, large windows, and a front porch with chairs.

7. The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges
2.0 star property
Historic Railroad District
9.6 out of 10, Exceptional, (118 reviews)
"My room was clean, bed was comfortable. It was really nice and central to restaurants, coffee shops and downtown. It was nice having a door code instead of keys etc. would stay here again"
Canada
Lindsay
The price is AED 336
AED 575 total
includes taxes & fees
2 Dec - 3 Dec
The Peerless Hotel by WanderLodges
A Victorian-style building with ornate architectural details, large windows, and a red door.

8. McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District
9.6 out of 10, Exceptional, (619 reviews)
"All good; would stay again. Great breakfast too"
United States
Elizabeth
The price is AED 653
AED 728 total
includes taxes & fees
2 Dec - 3 Dec
McCall House Boutique Inn
An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.

9. Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1,797 reviews)
"Nice little hotel that was well decorated for the holiday."
United States
Thomas
The price is AED 376
AED 419 total
includes taxes & fees
2 Nov - 3 Nov
Stratford Inn
A balcony with a view of a residential area, a black pickup truck, and a white RV parked in the foreground.

10. Ashland Commons Hostel

Ashland Commons Hostel
2.0 star property
Ashland
9.4 out of 10, Exceptional, (75 reviews)
"Great place to stay. Excellent location."
United States
Sam
The price is AED 245
AED 274 total
includes taxes & fees
2 Nov - 3 Nov
Ashland Commons Hostel
A two-story house with a porch, surrounded by a well-maintained garden with various flowers and shrubs.

11. Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn
3.5 star property
Skidmore Academy Historic District
9.4 out of 10, Exceptional, (66 reviews)
"I have stayed in many bed and breakfasts over the years and this one ranks a perfect 10! Very clean,very friendly hosts, the absolute best breakfast of any B & B I've been to. If I'm going through Ashland in the future, this is my go to lodging. This felt like home! Hosts also were extremely helpful and knowledgeable about local dining. "
United States
Kim
The price is AED 955
AED 1,065 total
includes taxes & fees
2 Nov - 3 Nov
Abigail’s Bed & Breakfast Inn
A grand lobby with a high ceiling, large windows, and a central staircase.

12. Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (1,003 reviews)
"Location is perfect for Ashland."
United States
Duff
The price is AED 344
AED 440 total
includes taxes & fees
1 Dec - 2 Dec
Ashland Springs Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

13. Palm Cottages

Palm Cottages
2.5 star property
Ashland
9.2 out of 10, Wonderful, (233 reviews)
"Palm Cottages is a clean and wonderful boutique hotel on the outskirts of downtown Ashland. We only stayed one night but we will definitely be back again some day. Thank you 🙏"
United States
Eric
The price is AED 746
AED 831 total
includes taxes & fees
2 Nov - 3 Nov
Palm Cottages
An outdoor dining area with a table set for two, surrounded by chairs, a red umbrella, and a stone water feature.

14. Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
3.0 star property
Ashland
9.0 out of 10, Wonderful, (1,002 reviews)
"Very nicece hotel and perfect location for walking and exploring Ashland."
United States
Heather
The price is AED 426
AED 475 total
includes taxes & fees
2 Nov - 3 Nov
Plaza Inn & Suites at Ashland Creek
A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

15. Timbers INN and Suites

Timbers INN and Suites
2.0 star property
Ashland
8.8 out of 10, Excellent, (1,002 reviews)
"Our room was very clean and comfortable and our staff interaction was great. We’ll definitely stay here again when we come to Ashland."
United States
Sarah
The price is AED 234
AED 261 total
includes taxes & fees
3 Nov - 4 Nov
Timbers INN and Suites
A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.

16. Prospero's Flagship Inn

Prospero's Flagship Inn
2.5 star property
Ashland
8.4 out of 10, Very good, (1,486 reviews)
"We enjoyed our stay very much. The location was good; the staff great and our room was very nice"
United States
Mary
The price is AED 228
AED 254 total
includes taxes & fees
5 Nov - 6 Nov
Prospero's Flagship Inn
A spacious lobby with a reception desk, seating area, and large windows.

17. 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
8.4 out of 10, Very good, (1,000 reviews)
"Location is very convenient to nice walks, restaurants and shops."
United States
Thomas
The price is AED 349
AED 389 total
includes taxes & fees
24 Nov - 25 Nov
The Bard's Inn, BW Signature Collection by Best Western
A hotel room with a desk, laptop, two beds, and a round mirror.

18. Ashland Motel - Oregon

Ashland Motel - Oregon
2.0 star property
Ashland
8.0 out of 10, Very good, (251 reviews)
"Clean, basic room that is walking distance to downtown Ashland."
United States
Madrik A.
The price is AED 258
AED 288 total
includes taxes & fees
2 Dec - 3 Dec
Ashland Motel - Oregon
A dining area with a wooden table and chairs, a potted plant, and a window with blinds.

19. Cedarwood Inn of Ashland

Cedarwood Inn of Ashland
2.0 star property
Ashland
7.4 out of 10, Good, (1,001 reviews)
"Good location, good value."
United States
Toby
The price is AED 256
AED 286 total
includes taxes & fees
9 Nov - 10 Nov
Cedarwood Inn of Ashland
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

20. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is AED 588
AED 1,265 total
includes taxes & fees
22 Nov - 23 Nov
Savage Upon Siskiyou
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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Choose what matters most at family-friendly hotels in Ashland

Breakfast included
Pool

Family-friendly hotels with free breakfast in Ashland

An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.
Stratford Inn

Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1797)
The price is AED 376
AED 419 total
includes taxes & fees
2 Nov - 3 Nov
Stratford Inn
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Family-friendly hotels with pools in Ashland

An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.
Stratford Inn

Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1797)
The price is AED 376
AED 419 total
includes taxes & fees
2 Nov - 3 Nov
Stratford Inn
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.
View all properties

Top Ashland Hotel Reviews

Timbers INN and Suites

Timbers INN and Suites

8/10 Good
"This small motel harkens back to the 50s without any of the stogginess. My room was perfectly clean and comfortable. The bed was comfy and everything else was just fine. I think the best thing was the motel is adjacent to a great pizza place! I will stay there again if I travel that way."
Patricia 1-night trip
Posted 21 hours ago
Timbers INN and Suites

Frequently asked questions

What's Ashland like for family-friendly vacations?
The welcoming destination of Ashland is a good choice if you've been considering a getaway with your kids. The entertainment, festivals, and hiking trails are just some of the things that make this an attractive family vacation spot. Take to the air and fly into Rogue Valley Intl. Airport (MFR), which is located 14.4 mi (23.3 km) from the city center.
What's the best hotel when traveling with kids to Ashland?
Plaza Inn & Suites at Ashland Creek is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly vacation in Ashland?
The hottest months are usually August and July with an average temp of 65°F, while the coldest months are December and January with an average of 37°F. Average annual precipitation for Ashland is 33 inches.
What's there to see and do with your family in Ashland?
While you and your family are visiting Ashland, you might want to check out some kid-friendly attractions such as Allen Elizabethan Theatre, Angus Bowmer Theatre, and Oregon Shakespeare Festival. Make sure you have lots of time for activities like Oregon Cabaret Theatre and Mount Ashland Ski Area.

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