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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Ashland cottages

A house with a wooden deck, a stone wall, and a wooden fence.

1. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (241 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is NZ$403
includes taxes & fees
27 Oct - 28 Oct
The Ashland Cottage, walk to town
A residential house with a garage, a satellite dish, and a driveway.

2. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely stay. "
United States
Cyndy K.
The price is NZ$405
includes taxes & fees
29 Oct - 30 Oct
Charming carriage house in Ashland near downtown
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

3. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (77 reviews)
"Excellent stay. Very responsive host. Would come back"
United States
Scott N.
The price is NZ$468
includes taxes & fees
27 Oct - 28 Oct
Courtside Cottage - WalkScore 93 - Dog Friendly
A pathway leading to a house with a wooden deck and a stone-paved area.

4. The Hideaway Cottage at Second Street Cottages

The Hideaway Cottage at Second Street Cottages
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Amazing property and a short walk to downtown. Fantastic hosts with great communication. I hope to rent again when we come back."
United States
Vicki
The price is NZ$544
includes taxes & fees
22 Nov - 23 Nov
The Hideaway Cottage at Second Street Cottages
A two-story house with a porch, a sign indicating it is a cottage, and a mailbox.

5. The Garden Cottage at Second Street Cottages

The Garden Cottage at Second Street Cottages
Historic Railroad District
10.0 out of 10, Exceptional, (8 reviews)
"Very comfortable and good location. Lovely furnishings and ambience."
United States
Barbara C.
The price is NZ$570
includes taxes & fees
3 Nov - 4 Nov
The Garden Cottage at Second Street Cottages
An outdoor patio with a grill, dining table, chairs, and string lights.

6. Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
The price is NZ$708
includes taxes & fees
3 Nov - 4 Nov
Paschal Winery
A house with a yellow door, a stone facade, and a garden with various flowers.

7. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (52 reviews)
"Good location and comfy beds!"
United States
Melissa L.
The price is NZ$377
includes taxes & fees
10 Nov - 11 Nov
Downtown Mint
Coffee and/or coffee maker

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

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Central Point
9.8 out of 10, Exceptional, (129 reviews)
"Wonderful stay and will definitely do so again!!!"
United States
Kelly B.
The price is NZ$312
includes taxes & fees
1 Nov - 2 Nov
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
A residential house with a front porch, a small garden with various plants and flowers, and a gravel driveway.

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

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Central Point
10.0 out of 10, Exceptional, (18 reviews)
"Everything was wonderful Will definitely stay again"
United States
Kellie P.
The price is NZ$341
includes taxes & fees
3 Nov - 4 Nov
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
A single-story house with a gabled roof, surrounded by a variety of plants and shrubs.

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

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (49 reviews)
"Amazing location and the interior design was fabulous! Has everything you need and my dog had a great time too! All around awesome place, would highly recommend."
United States
Houda
The price is NZ$464
includes taxes & fees
1 Nov - 2 Nov
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
A cabin with a stone exterior, a porch with a red door, and a sign reading "The Cottage."

11. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
10.0 out of 10, Exceptional, (2 reviews)
"Thank you, this was a very clean, attractive property with everything needed. Maricio was the host & he was very attentive, kind & quick to respond . I highly recommend this property, it’s in a nice area & fun places to explore. Thanks for a great visit!"
United States
Jayne
The price is NZ$393
includes taxes & fees
27 Oct - 28 Oct
Forest Cabin by Crater Lake & Klamath Falls
A bedroom with a bed, a TV, a ladder, a mirror, a basket, and a door with a 'No Smoking' sign.

12. Rosewood Studio | Private Cottage Near Downtown

Rosewood Studio | Private Cottage Near Downtown
Medford
8.0 out of 10, Very good, (1 review)
"Location was as advertised."
United States
william L.
The price is NZ$320
includes taxes & fees
29 Oct - 30 Oct
Rosewood Studio | Private Cottage Near Downtown
A two-story house with a front porch, a covered entryway, and a small front yard.

13. Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.

Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
Jacksonville Historic District
9.8 out of 10, Exceptional, (85 reviews)
"What an adorable cottage. It’s right in town but on a quiet street. It had every amenity that we needed. I would very highly recommend and would stay here again"
United States
Richard
The price is NZ$506
includes taxes & fees
29 Oct - 30 Oct
Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
A small, single-story house with a white picket fence, a purple front door, and a porch with white railings.

14. Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (71 reviews)
"We’ve stayed in Vrbo’s around the world and this is by far our favorite."
United States
Robert B.
Historic Bradshaw House!
A blue house with a patio, a small table and chairs, and a hanging flower basket.

15. Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Central Point
9.6 out of 10, Exceptional, (40 reviews)
"Lovely cottage with all the amenities in the countryside with beautiful views down a quiet lane. Perfect for our stay to visit Jacksonville and easy access to Medford airport."
United States
Vanessa C.
The price is NZ$452
includes taxes & fees
1 Nov - 2 Nov
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
A bedroom with a fireplace, a bed with a headboard, a window, and a wall-mounted picture.

16. Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.

Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
Jacksonville
9.6 out of 10, Exceptional, (4 reviews)
"Excellent location. The house was comfortable and had everything we needed."
United States
Christopher
The price is NZ$556
includes taxes & fees
30 Oct - 31 Oct
Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
A house with a stone pathway, white picket fence, and a small porch.

17. Charming 1BR Cottage – Walk to Britt Gardens

Charming 1BR Cottage – Walk to Britt Gardens
Jacksonville
9.2 out of 10, Wonderful, (9 reviews)
"Location and interior was superb"
United States
Jonathan B.
The price is NZ$460
includes taxes & fees
10 Nov - 11 Nov
Charming 1BR Cottage – Walk to Britt Gardens
A small house with a porch, a bench, and a tree with white blossoms.

18. Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Jacksonville
9.8 out of 10, Exceptional, (38 reviews)
"What a great location! We mostly sat by the river and enjoyed the scenery!"
United States
Christina B.
The price is NZ$386
includes taxes & fees
19 Nov - 20 Nov
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
A two-story house with a sloped roof, multiple windows, and a well-maintained garden.

19. Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget friendly.

Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget friendly.
Central Point
9.0 out of 10, Wonderful, (7 reviews)
"So easy to get in and out. Convenient to everything we did in the valley. Exactly as advertised. Great views and quiet location. Will definitely book again when in town. "
United States
Marc A.
The price is NZ$543
includes taxes & fees
18 Nov - 19 Nov
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget friendly.
A residential property with a paved driveway leading to a front door, a wooden fence, and a small garden area.

20. The Williams - Luxury 2-bedroom with On-Site Parking in Downtown Jacksonville

The Williams - Luxury 2-bedroom with On-Site Parking in Downtown Jacksonville
Jacksonville Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful place and great location"
United States
darren t.
The price is NZ$663
includes taxes & fees
2 Nov - 3 Nov
The Williams - Luxury 2-bedroom with On-Site Parking in Downtown Jacksonville
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

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

10/10 Excellent
"This was our second stay at Comfort Inn & Suites in Ashland. We’ve been so impressed with the friendly, professional staff and cleanliness of the hotel in general, we recommended it to some friends!"
Nancy 1-night trip
Posted 12 hours ago
Comfort Inn & Suites Ashland

Find out more about Ashland

Ashland Cottages information

Number of reviews
809
Accommodation
121 Cottages
Lowest Price
NZ$312
Highest Price
NZ$708

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between NZ$312 and NZ$708 per night. These properties offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Ashland?
Pack your suitcase and pick from 121 cottages in Ashland. Longing for a place where you can relax and connect with nature? Expedia will help you find your ideal retreat in only a click or two.
What is there to do in Ashland near my cottage?
Whatever you're interested in, Ashland has plenty to keep you entertained. Emigrant Lake, Angus Bowmer Theatre and ScienceWorks Hands-On Museum are on many visitors' sightseeing plans. Don't miss North Mountain Park, Mount Ashland Ski Area and Allen Elizabethan Theatre either. With Expedia's Ashland hotel deals, you can see more fantastic attractions like these with the cash you save.

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