Oak Street Cottages

A Romantic Escape in Downtown Ashland, Oregon

Located steps from Ashland’s vibrant downtown, Oak Street Cottages offers a unique blend of historic charm, privacy, and comfort, making it a top choice for couples seeking a romantic getaway or couples retreat.

These individually-designed cottages offer all the privacy and coziness of your own home, complemented by lush gardens and a quaint, tree-lined setting.

Historic Touches, Modern Comforts

The story of Oak Street Cottages dates back to the 19th century, with the original Sherwin House reflecting Ashland’s historic character. Thoughtfully restored and family-run, each cottage boasts inviting interiors, charming architectural details, and amenities designed for comfort and romance.

Cottage Features & Layouts

Choose from several cottages and studios:

• Sherwin Cottage: Historic, spacious, and perfect for couples who appreciate period charm.
• Oak Lawn Cottage: Cozy and private, with a fireplace and covered patio for enchanting evenings.
• Oak Hideaway: Ground-level, accessible, and featuring faux-finished walls, ideal for relaxing after a day’s adventures.
• Oak Tower: Sunlit living spaces with a private deck, perfect for coffee at sunrise or a romantic evening meal.
• Oak Studio: Ground-level space flooded with afternoon light, great for a secluded retreat.

Romantic Amenities & Atmosphere

Every cottage is fully appointed for relaxation and connection, featuring:

• Fireplaces to create a warm and intimate ambiance
• Queen or king beds for restful nights
• Private patios or decks, some with garden views
• Outdoor dining with gas barbecue grills, ideal for evening meals under the stars
• Cozy living and dining areas for shared moments
• Complimentary off-street parking and free WiFi

The grounds exude storybook charm, with white picket fences, vibrant window boxes, and blooming gardens. Enjoy your morning coffee in a peaceful outdoor setting or savor a glass of local wine on your private patio.

Central, Walkable Location for Couples

Experience the best of Ashland on foot. Oak Street Cottages is just:

• A short walk from the renowned Oregon Shakespeare Festival theaters
• Steps to beautiful Lithia Park and Ashland Creek’s tranquil paths
• Surrounded by inviting restaurants, cafés, wine bars, and boutique shopping

Couples can enjoy romantic evenings at nearby fine dining establishments or catch a live performance, then return to their inviting cottage retreat.

Guest Experience: Comfort, Cleanliness, and Thoughtful Touches

Glowing reviews highlight the immaculate accommodations and spacious, comfortable layouts. Guests appreciate the well-kept amenities, modern updates, and thoughtful flourishes, such as fresh-baked bread and a welcoming bottle of wine. Friendly service and a focus on guest well-being make every stay memorable.

Local Adventures & Activities

Oak Street Cottages places you in the heart of Southern Oregon’s cultural and natural experiences:

• Renowned theater, music, and film festivals
• Endless trails for hiking and cycling
• Day trips to Crater Lake or Emigrant Lake
• Wine tasting at over 90 local wineries

Who Is This Retreat Best For?

Oak Street Cottages offers exceptional value for couples seeking an urban escape with the perfect blend of convenience, privacy, and romance. Whether celebrating an anniversary, planning a weekend getaway, or attending Ashland’s many cultural events, these charming cottages provide the ideal home base.

Why Choose Oak Street Cottages for Your Romantic Getaway?

• Prime Downtown Location: Walk to theaters, parks, cafes, and galleries.
• Enchanted Gardens & Historic Architecture: Inviting grounds and a sense of old-world charm.
• Privacy & Comfort: Fully independent cottages with all amenities.
• Romantic Touches: Fireplaces, patios, and a secluded feel perfect for couples.

Enjoy Ashland, reconnect, and create lasting memories, all from the restful comfort of your own cozy, romantic cottage.