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Check availability on Ashland Hotels with a Pool

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

Our top choices for Ashland hotels with a pool

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 ￥19,264
￥41,683 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥16,149
￥30,128 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥25,383
￥51,140 total
includes taxes & fees
Nov 4 - Nov 5
The Mountain Ave House by WanderLodges
A swimming pool at night with lounge chairs and a warning sign about no lifeguard on duty.

4. 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 ￥21,553
￥24,033 total
includes taxes & fees
Nov 3 - Nov 4
Arden Forest Inn
A large, two-story house with a wrap-around porch and a steeply pitched roof.

5. 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 ￥21,046
￥25,982 total
includes taxes & fees
Nov 9 - Nov 10
Winchester Inn
A two-story building with a wooden facade, large windows, and a front porch with chairs.

6. 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 ￥14,263
￥24,511 total
includes taxes & fees
Dec 3 - Dec 4
The Peerless Hotel by WanderLodges
A Victorian-style building with ornate architectural details, large windows, and a red door.

7. 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 ￥27,725
￥30,914 total
includes taxes & fees
Dec 3 - Dec 4
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.

8. 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 ￥16,126
￥17,981 total
includes taxes & fees
Nov 3 - Nov 4
Stratford Inn
A balcony with a view of a residential area, a black pickup truck, and a white RV parked in the foreground.

9. 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 ￥10,418
￥11,616 total
includes taxes & fees
Nov 3 - Nov 4
Ashland Commons Hostel
A two-story house with a porch, surrounded by a well-maintained garden with various flowers and shrubs.

10. 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 ￥40,966
￥45,677 total
includes taxes & fees
Nov 3 - Nov 4
Abigail’s Bed & Breakfast Inn
A grand lobby with a high ceiling, large windows, and a central staircase.

11. 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 ￥14,744
￥18,886 total
includes taxes & fees
Dec 1 - Dec 2
Ashland Springs Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

12. 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 ￥31,982
￥35,659 total
includes taxes & fees
Nov 3 - Nov 4
Palm Cottages
An outdoor dining area with a table set for two, surrounded by chairs, a red umbrella, and a stone water feature.

13. 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 ￥18,292
￥20,395 total
includes taxes & fees
Nov 3 - Nov 4
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.

14. 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 ￥9,916
￥11,057 total
includes taxes & fees
Nov 12 - Nov 13
Timbers INN and Suites
A poolside area with lounge chairs and umbrellas, a pool, and a view of trees and mountains.

15. Prospero's Flagship Inn

Prospero's Flagship Inn
2.5 star property
Ashland
8.4 out of 10, Very good, (1,488 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 ￥9,758
￥10,879 total
includes taxes & fees
Nov 5 - Nov 6
Prospero's Flagship Inn
A pool area with lounge chairs and a covered seating area.

16. 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, (1,001 reviews)
"Location is very convenient to nice walks, restaurants and shops."
United States
Thomas
The price is ￥14,970
￥16,691 total
includes taxes & fees
Nov 24 - Nov 25
The Bard's Inn, BW Signature Collection by Best Western
A clear swimming pool with a wooden fence, surrounded by lounge chairs.

17. 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 ￥9,898
￥11,037 total
includes taxes & fees
Nov 14 - Nov 15
Ashland Motel - Oregon
A swimming pool with a wooden deck, a lifebuoy, and white plastic chairs.

18. 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 ￥10,872
￥12,122 total
includes taxes & fees
Nov 4 - Nov 5
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.

19. 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 ￥25,210
￥54,285 total
includes taxes & fees
Nov 22 - Nov 23
Savage Upon Siskiyou
A backyard with a swimming pool, patio furniture, a small pond, and a wooden cabin.

20. Country Willows Inn and Estate

Country Willows Inn and Estate
4.0 star property
Ashland
9.8 out of 10, Exceptional, (45 reviews)
"A beautiful serene landscape compliments the beautifully decorated and very comfy rooms. Beds and pillows were divine. Breakfast was epicurean."
United States
Diane
The price is ￥25,949
￥26,338 total
includes taxes & fees
Nov 3 - Nov 4
Country Willows Inn and Estate
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 hotels with a pool in Ashland

Breakfast included
Hot tub

Hotels with pools and free breakfast in Ashland

A Holiday Inn Express hotel with a two-story structure, a parking lot, and a landscaped area with shrubs and a tall tree.
Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
2.5 star property
Ashland
9.4 out of 10, Exceptional, (1001)
The price is ￥14,496
￥16,163 total
includes taxes & fees
Dec 2 - Dec 3
Holiday Inn Express & Suites Ashland by IHG
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Hotels with pools and hot tubs 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 ￥16,126
￥17,981 total
includes taxes & fees
Nov 3 - Nov 4
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.
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Top Ashland Hotel Reviews

Frequently asked questions

What's it like visiting Ashland?
If lounging by a pool is your idea of the perfect getaway, you might want to think about welcoming Ashland, which offers 10 places to stay with pools. While you're visiting, you can explore attractions like Allen Elizabethan Theatre and Angus Bowmer Theatre, and then take it easy poolside at one of the accommodations in Ashland that guests like for their pools.
What are some hotels with pools in Ashland?
Prospero's Flagship Inn: Features daily, a seasonal outdoor pool, and free self parking. Stratford Inn: Offers a children's pool, an indoor pool, and free self parking. Country Willows Inn and Estate: Provides spa services, a seasonal outdoor pool, and full. Arden Forest Inn: Features a snack bar/deli, a seasonal outdoor pool, and free self parking. Come stay at our farmhouse! A place to integrate all the beauty surrounding you!: Offers complimentary wireless internet access, a pool, and kitchens.
How many pool hotels are there in Ashland?
Expedia has 10 hotels in Ashland for your poolside break.
What is there to see and do in Ashland?
Make a point to visit attractions like Lithia Park and ScienceWorks Hands-On Museum. Discover sights such as Allen Elizabethan Theatre, Angus Bowmer Theatre, and Oregon Shakespeare Festival during your stay. Ashland appeals to visitors with its picturesque gardens, popular theater scene, and array of dining options.
When is the best time to book a hotel with a pool in Ashland?
Taking into account the local weather in Ashland is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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.