A town with buildings and trees in autumn colors, surrounded by mountains.

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Our top choices for Skidmore Academy Historic District hotels

1. 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 £216
includes taxes & fees
4 Nov - 5 Nov
Abigail’s Bed & Breakfast Inn

2. Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District, 1.3 mi from Skidmore Academy Historic District
9.4 out of 10, Exceptional, (1,801 reviews)
"Nice little hotel that was well decorated for the holiday."
United States
Thomas
The price is £85
includes taxes & fees
4 Nov - 5 Nov
Stratford Inn

3. Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District, 1 mi from Skidmore Academy Historic District
9.2 out of 10, Wonderful, (1,007 reviews)
"Location is perfect for Ashland."
United States
Duff
The price is £90
includes taxes & fees
1 Dec - 2 Dec
Ashland Springs Hotel

4. Prospero's Flagship Inn

Prospero's Flagship Inn
2.5 star property
2 mi from Skidmore Academy Historic District
8.4 out of 10, Very good, (1,493 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 £52
includes taxes & fees
5 Nov - 6 Nov
Prospero's Flagship Inn

5. 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, 0.7 mi from Skidmore Academy Historic District
8.4 out of 10, Very good, (1,002 reviews)
"Location is very convenient to nice walks, restaurants and shops."
United States
Thomas
The price is £79
includes taxes & fees
24 Nov - 25 Nov
The Bard's Inn, BW Signature Collection by Best Western

6. Lithia Springs Resort

Lithia Springs Resort
3.0 star property
1.4 mi from Skidmore Academy Historic District
9.4 out of 10, Exceptional, (1,006 reviews)
"Modern rooms, well thought out. Really enjoyed the stay, was not a “just sleep” motel but a nice relaxing mini resort!"
United States
Matthew
The price is £86
includes taxes & fees
16 Nov - 17 Nov
Lithia Springs Resort

7. Timbers INN and Suites

Timbers INN and Suites
2.0 star property
2.3 mi from Skidmore Academy Historic District
8.8 out of 10, Excellent, (1,003 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 £52
includes taxes & fees
9 Nov - 10 Nov
Timbers INN and Suites

8. Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
1.6 mi from Skidmore Academy Historic District
9.0 out of 10, Wonderful, (1,065 reviews)
"Clean rooms, good breakfast, conveniently located."
United States
Bill
The price is £75
includes taxes & fees
2 Dec - 3 Dec
Comfort Inn & Suites Ashland

9. Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
3.0 star property
0.6 mi from Skidmore Academy Historic District
9.0 out of 10, Wonderful, (1,004 reviews)
"Very nicece hotel and perfect location for walking and exploring Ashland."
United States
Heather
The price is £97
includes taxes & fees
4 Nov - 5 Nov
Plaza Inn & Suites at Ashland Creek

10. Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
2.5 star property
3.5 mi from Skidmore Academy Historic District
9.2 out of 10, Wonderful, (1,004 reviews)
"Very friendly staff."
Canada
Tanis
The price is £76
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Express & Suites Ashland by IHG

11. The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges
2.0 star property
Historic Railroad District, 1.1 mi from Skidmore Academy Historic 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 £109
includes taxes & fees
5 Nov - 6 Nov
The Peerless Hotel by WanderLodges

12. Best Western Windsor Inn

Best Western Windsor Inn
2.5 star property
3.5 mi from Skidmore Academy Historic District
9.0 out of 10, Wonderful, (1,004 reviews)
"Great location, clean room, friendly staff"
United States
Ross
The price is £94
includes taxes & fees
10 Nov - 11 Nov
Best Western Windsor Inn

13. Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
3.5 mi from Skidmore Academy Historic District
8.8 out of 10, Excellent, (1,580 reviews)
"Clean rooms, nice location."
United States
Nicholas
The price is £89
includes taxes & fees
12 Nov - 13 Nov
Ashland Hills Hotel & Suites

14. Winchester Inn

Winchester Inn
3.5 star property
Historic Downtown District, 1 mi from Skidmore Academy Historic District
9.6 out of 10, Exceptional, (291 reviews)
"Amazing breakfasts, friendly staff, best location"
United States
Ellen
The price is £114
includes taxes & fees
5 Nov - 6 Nov
Winchester Inn

15. Ashland Commons Hostel

Ashland Commons Hostel
2.0 star property
1.1 mi from Skidmore Academy Historic District
9.4 out of 10, Exceptional, (75 reviews)
"Great place to stay. Excellent location."
United States
Sam
The price is £56
includes taxes & fees
4 Nov - 5 Nov
Ashland Commons Hostel

16. Cedarwood Inn of Ashland

Cedarwood Inn of Ashland
2.0 star property
2.8 mi from Skidmore Academy Historic District
7.4 out of 10, Good, (1,001 reviews)
"Good location, good value."
United States
Toby
The price is £56
includes taxes & fees
9 Nov - 10 Nov
Cedarwood Inn of Ashland

17. Ashland Motel - Oregon

Ashland Motel - Oregon
2.0 star property
2 mi from Skidmore Academy Historic District
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 £59
includes taxes & fees
4 Dec - 5 Dec
Ashland Motel - Oregon

18. Baymont by Wyndham

Baymont by Wyndham
2.5 star property
3.2 mi from Skidmore Academy Historic District
7.8 out of 10, Good, (708 reviews)
"It was quiet, clean and reasonably priced. The wi fi worked well in the room"
United States
Virginia
The price is £70
includes taxes & fees
13 Nov - 14 Nov
Baymont by Wyndham

19. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
1.5 mi from Skidmore Academy Historic District
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is £199
includes taxes & fees
4 Nov - 5 Nov
Barclay Klum House by WanderLodges

20. McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District, 0.8 mi from Skidmore Academy Historic District
9.6 out of 10, Exceptional, (619 reviews)
"All good; would stay again. Great breakfast too"
United States
Elizabeth
The price is £156
includes taxes & fees
4 Nov - 5 Nov
McCall House Boutique 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.

Compare popular hotels in Skidmore Academy Historic District

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A two-story house with a porch, surrounded by a well-maintained garden with various flowers and shrubs.
Abigail’s Bed & Breakfast Inn
3.5 star property
9.4
Exceptional
66 reviews
View
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
2.5 star property
9.4
Exceptional
1,801 reviews
View
A hotel entrance with outdoor seating, potted plants, and a well-lit facade.
Comfort Inn & Suites Ashland
2.5 star property
9.0
Wonderful
1,065 reviews
View
An outdoor patio area with tables and chairs, string lights, and potted plants.
Ashland Springs Hotel
3.0 star property
9.2
Wonderful
1,007 reviews
View
An outdoor dining area with a table set for two, surrounded by chairs, a red umbrella, and a stone water feature.
Plaza Inn & Suites at Ashland Creek
3.0 star property
9.0
Wonderful
1,004 reviews
View

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

Frequently asked questions

What other neighbourhoods are similar to Skidmore Academy Historic District?
While the Skidmore Academy Historic District is unique, the closest neighbourhoods in terms of historic character and walkability are the Pearl District and the Nob Hill area in Northwest Portland.

The Pearl District, just south of the Skidmore Academy Historic District, is a former industrial area transformed into a lively urban hub. It's known for its renovated warehouses now housing art galleries, boutiques, and high-end restaurants. The area is particularly popular with couples who appreciate its sophisticated dining options, numerous independent shops, and proximity to cultural venues like Powell's City of Books. It's also well-connected by public transport, making it easy to explore other parts of the city.

Nob Hill, located slightly to the west of the Skidmore Academy Historic District, offers a more residential feel with beautiful Victorian and Craftsman-style homes. Its main thoroughfare, NW 23rd Avenue, is lined with independent boutiques, cafes, and restaurants, making it ideal for those who enjoy leisurely strolls and discovering unique local businesses.
What are the most romantic hotels in Skidmore Academy Historic District for couples?
For a romantic stay in the Skidmore Academy Historic District, Abigail's Bed & Breakfast Inn is an excellent choice for couples.

This 3.5-star inn, with an impressive 9.4 rating, offers a delightful experience for couples. Guests can enjoy the scenic mountain views and take advantage of nearby winery tours or even private vineyard tours. The inn is conveniently located just 1.0 km from the Allen Elizabethan Theatre, superb for an evening out.
What are the best hotels in Skidmore Academy Historic District near Lithia Park?
For a highly-rated hotel in Skidmore Academy Historic District near Lithia Park, Abigail's Bed & Breakfast Inn is an excellent choice.

This 3.5-star inn has an outstanding 9.4 rating and is located 1.7 km from Lithia Park. Guests can enjoy mountain views and the inn is conveniently located for winery tours, with a vineyard on-site. The Oregon Shakespeare Festival, Ashland Library, Allen Elizabethan Theatre, and Angus Bowmer Theatre are also within easy reach.
When is the best time to go to Skidmore Academy Historic District?
The best time to go to the Skidmore Academy Historic District is during the late spring (May to early June) or early autumn (September to October) when the weather is pleasant and the district is at its most inviting.

During late spring, the gardens and green spaces are in full bloom, making it a beautiful time for strolls. The temperatures are mild, typically ranging from 15°C to 22°C (59°F to 72°F), superb for exploring the outdoor exhibits and architecture. You'll find fewer crowds compared to the peak summer months, allowing for a more relaxed experience. This period is particularly good for history enthusiasts and couples who appreciate comfortable weather for walking tours and outdoor dining.

Early autumn also offers agreeable weather, with temperatures usually between 12°C and 20°C (54°F to 68°F), and the changing leaves add a lovely touch to the historic surroundings. This season often brings clear, crisp days ideal for photography and outdoor activities. It's an excellent time for those who prefer a quieter visit, avoiding the summer rush, while still enjoying the full range of attractions.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Skidmore Academy Historic District.
How much is the nightly rate at a Skidmore Academy Historic District hotel?
Hotel prices in Skidmore Academy Historic District often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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