Ashland Cottages

A deer on a road with vegetation on the sides.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Ashland cottages

A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

1. Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District

John B.

A house with a driveway, a tree in the front yard, and a rainbow in the background.

2. Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Ashland

Greg M.

includes taxes & fees

14 Sept - 15 Sept

A residential house with a garage, a satellite dish, and a driveway.

3. Charming carriage house in Ashland near downtown

Skidmore Academy Historic District

Cyndy K.

An outdoor patio with a grill, dining table, chairs, and string lights.

4. Paschal Winery

Talent

Christine

includes taxes & fees

27 Sept - 28 Sept

A residential house with a front porch, a small garden with various plants and flowers, and a gravel driveway.

5. Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

Central Point

Kellie P.

includes taxes & fees

21 Sept - 22 Sept

A bedroom with a bed, a TV, a ladder, a mirror, a basket, and a door with a 'No Smoking' sign.

6. Rosewood Studio | Private Cottage Near Downtown

Medford

william L.

includes taxes & fees

12 Sept - 13 Sept

A single-story house with a gabled roof, surrounded by a variety of plants and shrubs.

7. HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

City Center Medford

Houda

includes taxes & fees

27 Sept - 28 Sept

8. Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Central Point

Chris A.

includes taxes & fees

15 Sept - 16 Sept

View all properties

Find holiday rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top Ashland Hotel Reviews

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"Great location, quiet area, loved being able to walk everywhere. Will go back again!"

Timbers INN and Suites

8/10 Good

"The Timbers Inn and Suites was perfect for our one night stay in Ashland. Our room had a small kitchenette, but was stocked with everything we needed. The room was small but for a one night stay it didn't matter. The staff was friendly. The room was clean (without counting a few cobwebs and a spider). Reasonably priced and close to downtown, it was a solid deal."

Ashland Springs Hotel

8/10 Good

"Historic building decorated Victorian eclectic, lovely lobby and rooms, comfortable beds and linens. Breakfast for $5 but wasn’t very good but for the price and convenience you can always have coffee and toast. The rooms really need a deep clean, carpets and sofa were in need of a shampoo. Bathroom was clean not much shelf space We had the 2queen room with a sitting area so comfortable. The best thing is location very short walk to shops restaurants and the theaters. I will stay here again."

Find out more about Ashland