Montgomery Cottages - Vacation Rentals in Oregon Shakespeare Festival

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From US $269

         

10.0 (211 Reviews)

Cottage

The Ashland Cottage, walk to town

• Air Conditioner
• Parking
• TV

• Medford
• Siskiyou-Hargadine Historic District

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From US $265

         

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9.0 (8 Reviews)

House

Bluemoon Vacation Rentals - Bluemoon Cottage

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Ashland

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From US $213

         

10.0 (59 Reviews)

Cottage

Courtside Cottage - WalkScore 93 - Dog Friendly

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Historic Downtown District

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From US $248

         

New

House

Cozy Modern Cottage

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Historic Railroad District

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From US $103

         

10.0 (18 Reviews)

Cottage

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

• Air Conditioner
• Parking
• TV

• Medford
• Ashland

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From US $152

         

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New

House

Warm and Inviting Ashland Cottage Less Than Half-Mile to SOU

• Parking
• Pet Friendly
• Wheelchair Accessible

• Medford
• Siskiyou-Hargadine Historic District

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From US $207

         

10.0 (6 Reviews)

Cottage

Charming carriage house in Ashland near downtown

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Skidmore Academy Historic District

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From US $374

         

10.0 (5 Reviews)

Cottage

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Ashland

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From US $201

         

10.0 (1 Review)

Cottage

Cozy Modern 1 Bedroom Cottage

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Historic Railroad District

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From US $186

         

10.0 (1 Review)

Cottage

Sage Ashland Cottage

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Siskiyou-Hargadine Historic District

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From US $254

         

9.8 (41 Reviews)

Cottage

Ashland's Mountain View Vacation Rental.

• Air Conditioner
• Parking
• TV

• Medford
• Ashland

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From US $405

         

9.6 (19 Reviews)

Cottage

Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Ashland

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From US $136

         

9.6 (4 Reviews)

Cottage

Thistlebee Cottage just outside charming Ashland, Oregon

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Ashland

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From US $407

         

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Cottage

Railroad District, steps to downtown, everything you need to enjoy Ashland!

• Air Conditioner
• Parking
• TV

• Medford
• Siskiyou-Hargadine Historic District

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From US $318

         

10.0 (93 Reviews)

Cottage

Stacy's 2nd St Cottage. Steps to downtown.

• Air Conditioner
• Parking
• TV

• Medford
• Historic Railroad District

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From US $212

         

10.0 (72 Reviews)

Cottage

The Terra Cottage Inn - Ashland, Oregon

• Air Conditioner
• Parking
• TV

• Medford
• Ashland

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From US $223

         

10.0 (69 Reviews)

Cottage

High Street Cottage Artists' Garden Cottage Clean & Beautiful

• Air Conditioner
• Parking
• TV

• Medford
• Historic Downtown District

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From US $218

         

10.0 (2 Reviews)

Cottage

ABBOTT'S COTTAGES- The Lark. 2 bedroom cottage, just two blocks to downtown

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Historic Railroad District

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From US $252

         

10.0 (1 Review)

Cottage

Abbott's Cottages- The Raven. Two bedroom cottage just two blocks to downtown.

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Historic Downtown District

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From US $181

         

10.0 (1 Review)

Cottage

The Indigo Cottage 5 Min walk to Downtown Ashland

• Pet Friendly
• Balcony/Terrace
• Security/Safety

• Medford
• Siskiyou-Hargadine Historic District

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From US $163

         

10.0 (1 Review)

Cottage

Abbott's Cottages- The Heron. One bedroom cottage just two blocks to downtown

• Air Conditioner
• Parking
• Pet Friendly

• Medford
• Ashland

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From US $142

         

10.0 (1 Review)

Cottage

ABBOTT'S COTTAGES- Duck cottage. 1 bedroom/1 bath, walking distance to downtown!

• Air Conditioner
• Parking
• TV

• Medford
• Ashland

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From US $176

         

9.8 (48 Reviews)

Cottage

Downtown Ashland private cottage with garden patio

• Air Conditioner
• Parking
• TV

• Medford
• Ashland

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From US $372

         

9.6 (14 Reviews)

Cottage

Walkable Retreat: Town and Theatre Two Bedroom Private Vacation Cottage.

• Air Conditioner
• Parking
• TV

• Medford
• Skidmore Academy Historic District

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★ Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Oregon Shakespeare Festival.