Skidmore Academy Historic District Hotels, Ashland

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29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

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Our top choices for Skidmore Academy Historic District hotels

Abigail Rockefeller
Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn
3.5 star property
Skidmore Academy Historic District
9.4 out of 10, Exceptional, (62)
"Best B and B in Ashland we have ever stayed at in thirty years . Amazing food and very comfortable."
United States
Andrew
The price is AU$299
includes taxes & fees
3 Jan - 4 Jan 2026
Abigail’s Bed & Breakfast Inn
Exterior
Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG
2.5 star property
23.6 km from Skidmore Academy Historic District
9.2 out of 10, Wonderful, (1010)
"Great room, quiet and clean. "
United States
james
The price is AU$164
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn Express Hotel & Suites Medford-Central Point by IHG
Lobby lounge
Springhill Suites By Marriott Medford Airport

Springhill Suites By Marriott Medford Airport

Springhill Suites By Marriott Medford Airport
3.0 star property
21.9 km from Skidmore Academy Historic District
9.6 out of 10, Exceptional, (1015)
"Very clean and very new hotel with excellent breakfast!"
Canada
Shaiba
The price is AU$184
includes taxes & fees
2 Jan - 3 Jan 2026
Springhill Suites By Marriott Medford Airport
Exterior detail
Stratford Inn

Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District, 2.1 km from Skidmore Academy Historic District
9.4 out of 10, Exceptional, (1626)
"Great place to stay. The room was very nice and staff were great."
United States
Dane
The price is AU$134
includes taxes & fees
30 Dec - 31 Dec
Stratford Inn
Exterior
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
2.6 km from Skidmore Academy Historic District
8.8 out of 10, Excellent, (1009)
"Staff was excellent and very nice and room was clean and location is good Town is very cool 👍"
United States
Thomas
The price is AU$122
includes taxes & fees
25 Jan - 26 Jan 2026
Comfort Inn & Suites Ashland
Free daily on-the-go breakfast
Flagship Inn of Ashland

Flagship Inn of Ashland

Flagship Inn of Ashland
2.5 star property
3.3 km from Skidmore Academy Historic District
8.8 out of 10, Excellent, (1207)
"Beautiful room and friendly staff. "
United States
Jackie
The price is AU$96
includes taxes & fees
31 Dec - 1 Jan 2026
Flagship Inn of Ashland
Full-sized fridge, stovetop, coffee/tea maker, toaster
My Place Hotel-Medford OR

My Place Hotel-Medford OR

My Place Hotel-Medford OR
3.0 star property
22.3 km from Skidmore Academy Historic District
9.2 out of 10, Wonderful, (1521)
"Clean room with good versatility, friendly staff and plenty of parking."
United States
DAVID J
The price is AU$148
includes taxes & fees
12 Jan - 13 Jan 2026
My Place Hotel-Medford OR
Lobby sitting area
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
5.6 km from Skidmore Academy Historic District
8.8 out of 10, Excellent, (1500)
"What a great place to stay"
United States
christine
The price is AU$165
includes taxes & fees
1 Jan - 2 Jan 2026
Ashland Hills Hotel & Suites
Garden
Ashland Springs Hotel

Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District, 1.5 km from Skidmore Academy Historic District
9.2 out of 10, Wonderful, (1001)
"Small room but wonderful view and comfortable bed. "
United States
Jessica
The price is AU$167
includes taxes & fees
4 Jan - 5 Jan 2026
Ashland Springs Hotel
View from property
Fairfield Inn & Suites by Marriott Medford

Fairfield Inn & Suites by Marriott Medford

Fairfield Inn & Suites by Marriott Medford
2.5 star property
15.4 km from Skidmore Academy Historic District
9.4 out of 10, Exceptional, (505)
"Staff was friendly and room was clean. "
United States
David
The price is AU$199
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield Inn & Suites by Marriott Medford
Exterior
Best Western Windsor Inn

Best Western Windsor Inn

Best Western Windsor Inn
2.5 star property
5.6 km from Skidmore Academy Historic District
9.0 out of 10, Wonderful, (1001)
"Staff was incredibly friendly, kept the room clean and assisted us with food recommendations."
United States
Isaac
The price is AU$181
includes taxes & fees
11 Jan - 12 Jan 2026
Best Western Windsor Inn
Exterior
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
5.7 km from Skidmore Academy Historic District
9.2 out of 10, Wonderful, (1000)
"Friendly staff, easy, check-in, close parking, clean rooms, quiet. Good breakfast. Hot cakes, bacon, sausage, eggs, cinnamon rolls, yogurt everything you could want."
United States
Tiea
The price is AU$173
includes taxes & fees
16 Jan - 17 Jan 2026
Holiday Inn Express & Suites Ashland by IHG
Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio
Callahan's Mountain Lodge

Callahan's Mountain Lodge

Callahan's Mountain Lodge
3.0 star property
17.9 km from Skidmore Academy Historic District
8.8 out of 10, Excellent, (1173)
"Very friendly staff in a gorgeous setting! "
United States
Patrick
The price is AU$172
includes taxes & fees
7 Jan - 8 Jan 2026
Callahan's Mountain Lodge
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, 1.1 km from Skidmore Academy Historic District
8.6 out of 10, Excellent, (1001)
"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 AU$174
includes taxes & fees
11 Jan - 12 Jan 2026
The Bard's Inn, BW Signature Collection by Best Western
In-room safe, desk, soundproofing, iron/ironing board
Comfort Inn Medford North

Comfort Inn Medford North

Comfort Inn Medford North
2.5 star property
20.4 km from Skidmore Academy Historic District
8.4 out of 10, Very good, (1005)
"I am checked in at Comfort Inn South."
United States
Patricia
The price is AU$121
includes taxes & fees
18 Jan - 19 Jan 2026
Comfort Inn Medford North
Exterior
Motel 6 Medford, OR - North

Motel 6 Medford, OR - North

Motel 6 Medford, OR - North
2.0 star property
20.5 km from Skidmore Academy Historic District
7.4 out of 10, Good, (1067)
"The room was good and location to the airport, however it is a little noisy at night with people coming and going."
United States
Lisa
The price is AU$68
includes taxes & fees
12 Jan - 13 Jan 2026
Motel 6 Medford, OR - North
Meeting facility
Hilton Garden Inn Medford, OR 

Hilton Garden Inn Medford, OR 

Hilton Garden Inn Medford, OR 
3.0 star property
15.6 km from Skidmore Academy Historic District
8.8 out of 10, Excellent, (1003)
"Location and restaurant on property "
United States
Katherine
The price is AU$154
includes taxes & fees
25 Jan - 26 Jan 2026
Hilton Garden Inn Medford, OR 
Indoor pool
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport
3.0 star property
20.5 km from Skidmore Academy Historic District
8.8 out of 10, Excellent, (2736)
"Clean, good area and good breakfast. "
United States
hope
The price is AU$143
includes taxes & fees
11 Jan - 12 Jan 2026
Rogue Regency Inn Medford Airport
Seasonal outdoor pool
Timbers INN and Suites

Timbers INN and Suites

Timbers INN and Suites
2.0 star property
3.7 km from Skidmore Academy Historic District
8.6 out of 10, Excellent, (1000)
"Courteous staff. Room was clean, and nice and hot for the winter cold outside. Plus, it's right next door to a great little pizza place!"
United States
Kevin
The price is AU$103
includes taxes & fees
30 Dec - 31 Dec
Timbers INN and Suites
Lobby
Hampton Inn Medford

Hampton Inn Medford

Hampton Inn Medford
2.5 star property
19.7 km from Skidmore Academy Historic District
8.6 out of 10, Excellent, (1001)
"Room was clean, staff was very helpful and breakfast was great."
United States
Ron
The price is AU$164
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn Medford
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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Our guide on where to stay in Skidmore Academy Historic District

Find the best Skidmore Academy Historic District areas for the activities you enjoy most.

Historic Downtown District

While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Oregon Shakespeare Festival.

Historic Railroad District

While Historic Railroad District isn't home to many top sights, Oregon Cabaret Theatre and Allen Elizabethan Theatre are some notable places to visit nearby.

Siskiyou-Hargadine Historic District

If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.

Top Skidmore Academy Historic District Hotel Reviews

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

10/10 Excellent
"Our room was as clean as one with many rooms to clean could make it. All of the staff were very friendly, and the breakfast was great. Premises seemed pretty safe as well. Would stay again."
Matt Allen 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

Frequently asked questions

What's it like in Skidmore Academy Historic District?
You'll be sure to have fun exploring Ashland's Skidmore Academy Historic District neighbourhood.
What's the best accommodation in Skidmore Academy Historic District?
Based on our traveller data, Abigail's Bed & Breakfast Inn is one of the top choices for your stay in Skidmore Academy Historic District. This B&B offers free parking and a snack bar/deli.
How many hotels will I find in Skidmore Academy Historic District?
Book one of Expedia's 5 hotels and other accommodation options in Skidmore Academy Historic District and start exploring everything Ashland has to offer.
If I need to cancel my hotel reservation in Skidmore Academy Historic District, will I receive a refund?
Yes, most hotel reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and get a refund within 24 hours of booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to review the best deals in Skidmore Academy Historic District.
What are the top things to see and do in Skidmore Academy Historic District?
Allen Elizabethan Theatre, Angus Bowmer Theatre and Thomas Theatre are just a few of the places to visit in and around Skidmore Academy Historic District. Oregon Shakespeare Festival and Oregon Cabaret Theatre are also worth a visit when you're out sightseeing in Ashland.

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