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Rates & Policies


Sherwin Cottage 

This cottage will sleep up to 11 people.

$350 per night quadruple occupancy

$99 cleaning fee

Oak Tower

This cottage will sleep up to 8 people.

$325 per night quadruple occupancy

$89 cleaning fee

Oak Lawn

Cottage sleeps up to 6 people.
$250 per night double occupancy

$69 cleaning fee 

Oak Hideaway

Cottage each sleeps up to 6 people.
$250 per night double occupancy

$69 cleaning fee 

Oak Street Studio

This cottage will sleep up to 4 people.
$135 per night double occupancy

$59 cleaning fee


  • Cleaning fee per cottage per reservation will be added as noted above

  • City, state & lodging taxes are not included in rates above

  • Rates are $20 extra per person per night beyond occupancy rate stated above


High season is March-October.
Low season rates (November-February) are 20% off, excluding certain holidays


With today's budget cuts, schools are struggling more than ever to provide their students with the richness of culture, theater, travel, and art. We here at Oak Street Cottages wish to support the youth and the adults who guide them, by providing discounts for groups who wish to experience Ashland's gifts of the arts. Many schools rent all four cottages for an extended educational experience, or you may use the space for an on-site class, complete with theaters just a block away!

We would love to enrich your students' experience by making it affordable. Please contact us to discuss your particular group's needs. Together we can maintain the arts for our children!





  • Check in 3:00 PM, check out 11:00 AM

  • Children of all ages are welcome

  • Pets are welcome! An additional pet fee will be added to the reservation

  • Additional occupancy charges and taxes will be added to the final invoice

  • No smoking or vaping indoors

  • Deposit refunded if reservation cancelled more than 30 days before stay


We will accommodate pets under most circumstances. Please call us regarding your specific request.  There will be a $20 fee for each pet pet night, plus a minimum charge of $150 if there are damages or extra cleaning needs. Each pet must be cleared with us before the reservation will be confirmed. 


Note: Primarily applies to high season dates. Policy may become lenient during low season. Please call for more info and for special cases.

The Oak Street Cottages is a small inn that often has no vacancy and will turn away inquiries, walk-ins, and other guests. For these reasons, we adhere to the following cancellation policy:

  • Deposits will be fully refunded if the reservation is cancelled at least thirty (30) days prior to day of check in.

  • Reservations cancelled within thirty (30) days of check in will forfeit the deposit and accrue a daily balance of the base rate on the reserved cottages that we cannot re-book. Cleaning fees will not be charged.

  • All attempts will be made to re-book the cottage.


Please contact us with any questions or special cases regarding our policies

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