Find Extended Stay Hotels in Historic Downtown District, OR

Top Historic Downtown District Extended Stay Hotels | Reserve now, pay later

Timbers INN and Suites
Seasonal outdoor pool

Timbers INN and Suites

2.0 star property
8.6 out of 10, Excellent, (1006)
"Great place to stay"
$79 nightly
The price is $89
Sep 29 - Sep 30
Total with taxes and fees
Timbers INN and Suites
Ashland Commons Hostel
Garden

Ashland Commons Hostel

2.0 star property
9.2 out of 10, Wonderful, (46)
"Another greet stay!"
$60 nightly
The price is $67
Sep 3 - Sep 4
Total with taxes and fees
Ashland Commons Hostel
Best Western Windsor Inn
Exterior

Best Western Windsor Inn

2.5 star property
9.0 out of 10, Wonderful, (1009)
"Our favorite place to stay in Ashland. Convenient location and great service!"
$113 nightly
The price is $125
Sep 28 - Sep 29
Total with taxes and fees
Best Western Windsor Inn
The Urban Gypsy Loft
Fridge, microwave, oven, coffee/tea maker

The Urban Gypsy Loft

9.8 out of 10, Exceptional, (6)
"We had the most amazing stay in Ashland at the Urban Gypsy Loft. Alisha was a wonderful host and her loft is absolutely adorable. The beds were big and SO comfortable. Perfect walking distance through the Historic District. Can't wait to visit again some day."
$230 nightly
The price is $256
Sep 2 - Sep 3
Total with taxes and fees
The Urban Gypsy Loft
Luxury condo with king bedroom, two bathrooms, full kitchen.
Fireplace

Luxury condo with king bedroom, two bathrooms, full kitchen.

10.0 out of 10, Exceptional, (8)
"A wonderful place in a perfect location"
$456 nightly
The price is $508
Sep 7 - Sep 8
Total with taxes and fees
Luxury condo with king bedroom, two bathrooms, full kitchen.
Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.
TV, offices

Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.

$1,348 nightly
The price is $1,503
Sep 2 - Sep 3
Total with taxes and fees
Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens.
5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.
Living area

5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.

10.0 out of 10, Exceptional, (4)
"Excellent"
$851 nightly
The price is $949
Oct 1 - Oct 2
Total with taxes and fees
5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.
2 bedrooms, office with sofa bed, sofa bed in living room, 3 bathrooms
Fridge, microwave, stovetop, coffee/tea maker

2 bedrooms, office with sofa bed, sofa bed in living room, 3 bathrooms

10.0 out of 10, Exceptional, (1)
"Probably the most luxurious accommodation in Ashland. Living the high life!"
$1,101 nightly
The price is $1,228
Sep 2 - Sep 3
Total with taxes and fees
2 bedrooms, office with sofa bed, sofa bed in living room, 3 bathrooms
Luxury condo with king bedroom, two bathrooms, full kitchen.
Fridge, microwave, stovetop, coffee/tea maker

Luxury condo with king bedroom, two bathrooms, full kitchen.

10.0 out of 10, Exceptional, (8)
"Great place"
$485 nightly
The price is $541
Sep 2 - Sep 3
Total with taxes and fees
Luxury condo with king bedroom, two bathrooms, full kitchen.
Luxury condo with 2 bedrooms/2 bathrooms, sleeper sofa, full kitchen.
Fridge, microwave, stovetop, coffee/tea maker

Luxury condo with 2 bedrooms/2 bathrooms, sleeper sofa, full kitchen.

10.0 out of 10, Exceptional, (5)
"We had a wonderful time exploring Ashland, going to wineries and hiking."
$570 nightly
The price is $636
Sep 2 - Sep 3
Total with taxes and fees
Luxury condo with 2 bedrooms/2 bathrooms, sleeper sofa, full kitchen.
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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