Luxury Vacation Rentals Oregon

Oregon offers a spectrum of destinations, each with its own sense of place and lifestyle. From coastal retreats to mountain towns and refined city enclaves, the following areas highlight where luxury living and travel in Oregon are most compelling.

Cannon Beach

Defined by Haystack Rock and refined coastal charm, Cannon Beach blends natural drama with upscale coastal dining and boutique galleries. Oceanfront estates place guests steps from the shoreline.

Manzanita

Intimate and quiet, Manzanita offers wide sandy beaches and a calming, low-key ambiance ideal for privacy-seekers. Discreet homes prioritize views, walkability, and easy beach access.

Pacific City

Set against Cape Kiwanda’s golden cliffs, Pacific City appeals to adventurous travelers with surfing, sand dunes, and scenic lookouts. Upscale rentals deliver panoramic views and direct access to the coast.

Gold Beach

On the rugged southern coast, Gold Beach pairs ocean bluffs with access to the Rogue River for jet-boat excursions and fishing. Properties emphasize seclusion, sweeping vistas, and a high degree of privacy.

Bend

Oregon’s mountain playground, Bend offers proximity to Mount Bachelor skiing, world-class hiking, and championship golf. Luxury homes balance alpine style with modern comforts and a thriving dining scene.

Redmond

Neighboring Bend, Redmond combines high-desert scenery with a relaxed pace and easy airport access. Estates often feature ranch-style layouts, acreage, and far-reaching Cascade views.

Willamette Valley

Wine country at its finest: rolling vineyards, boutique wineries, and chef-driven dining. Vineyard estates and luxury homes create immersive stays centered on tastings, terroir, and culinary experiences.

Lake Oswego

One of Oregon’s most exclusive suburban enclaves, Lake Oswego offers lakeside estates and hillside homes minutes from Portland’s culture. Expect manicured neighborhoods, parks, and refined local dining.

Portland

Southwest Hills features historic and contemporary homes with skyline and mountain views. The Pearl District is known for upscale penthouses and modern lofts, while Dunthorpe offers private estates in a wooded, residential setting.

West Linn

Lush landscapes and elegant estates define West Linn’s serene, family-forward prestige. Guests appreciate the quiet residential feel, river views, and proximity to Portland’s amenities.

Oregon’s culinary landscape is defined by its creativity and connection to place, where Pacific Northwest ingredients meet world-class preparation. From Portland’s refined urban dining rooms to intimate coastal restaurants and trusted favorites in Central Oregon, the state offers experiences that balance sophistication with a sense of locale.

El Gaucho, Portland

An elegant steakhouse specializing in Angus beef and premium seafood, El Gaucho pairs classic luxury dining with private rooms, fine wines and a refined, romantic atmosphere.

Arden, Portland

Set in the Pearl District, Arden highlights seasonal Pacific Northwest cuisine with a thoughtful wine list and intimate dining spaces, reflecting Portland’s culinary sophistication.

Stephanie Inn Dining Room, Cannon Beach

Overlooking the Pacific, this renowned restaurant blends ocean views with coastal-inspired cuisine in an elegant setting, making it a highlight for luxury travelers on the coast.

Brickhouse, Redmond

Known for well-prepared steaks, fine wines and attentive service, Brickhouse offers an upscale steakhouse experience in Central Oregon, popular for special occasions.

Oregon’s cultural offerings extend well beyond its landscapes, with art, history and creativity woven into local life. From private museums to intimate studios and distinctive folk-art landmarks, guests can elevate their experience through by-request private access and personalized encounters, subject to venue availability.

Erickson Aircraft Collection

This renowned collection features more than 20 rare WWII aircraft, many maintained in flying condition. Located in Madras, about 40 minutes from Bend, the museum operates seasonally and also hosts the annual Airshow of the Cascades. When active, guests may book Living History Flight Experiences for an exclusive perspective on aviation heritage. Advance confirmation is essential.

High Desert Museum (Bend)

Central Oregon’s flagship cultural institution brings together art, history, and natural sciences in immersive exhibits. Private and after-hours packages are available, allowing guests to explore curated galleries and wildlife programs in an elevated, exclusive setting.

Petersen Rock Garden & Museum

A historic folk-art landmark established in 1935, Petersen Rock Garden is celebrated for its intricate stone miniatures and resident peacocks. The site is open daily in summer (10:00–16:00) and Friday–Sunday in winter (10:00–14:00). For discerning travelers, direct inquiries can be made regarding private access and guided interpretation.

Oregon’s cultural calendar features elevated wine and culinary gatherings, coastal retreats, and intimate harvest celebrations that appeal to sophisticated travelers.

Oregon Truffle Festival

A celebrated winter culinary event in Astoria, offering tastings, chef-led experiences, and truffle-themed programming at historic venues like the Liberty Theatre. A refined escape for epicurean adventurers.

Pendleton Round-Up

The Pendleton Round-Up has been running in Oregon since 1910. This iconic rodeo pairs heritage with luxe experiences, from VIP seating to private hospitality.

Field & Vine Oregon Coast Getaway

An exclusive coastal retreat based in Depoe Bay, offering curated meals, seasonal activities, and boutique hotel access for a limited group. A seamless blend of coastal beauty and upscale hospitality.

Beyond its coastlines and vineyards, Oregon offers immersive experiences that balance outdoor adventure with refined service. Each activity can be tailored privately with expert guides and concierge support, subject to availability.

Private Wine Country Helicopter Tour

Lift over the Willamette Valley for vineyard landings and curated tastings on a seasonal private helicopter tour. Custom off-season arrangements are available by request through established operators.

Exclusive Fly-Fishing on the Deschutes River

Fish iconic waters with a private guide using drift boats for access and wade fishing in accordance with local regulations. Outfitters handle permits and logistics with gourmet provisions available on request.

Private Coastal Boat Charter

Explore the Pacific on a privately chartered vessel from Depoe Bay or Newport with bespoke whale watching and scenic coastline routes. Operators offer full-boat charters and special events with LVH arranging premium catering on request.