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Oakland House Seaside Inn and Cottages

4.7(91)
Services

About

The Oakland House Seaside Inn and Cottages offers a historic retreat on 60 acres overlooking Penobscot Bay, with views of Pumpkin Island and the Deer Isle Bridge. Its seven vintage cottages and a communal guest house provide cozy, well-appointed spaces with granite fireplaces and classic Maine charm, ideal for intimate corporate retreats or small group gatherings.

Onsite amenities include private beaches, hiking trails, and a large barn with a granite fireplace and high rafters for meetings or receptions. The experienced concierge team supports event planning and outdoor adventures, making the Oakland House a distinctive venue for business events that blend relaxation with nature-inspired activities.

Best for

  • Executive retreats with lakeside hiking
  • Small group meetings in vintage cottages
  • Team bonding around fireplace gatherings

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Custom Package Request

Custom request

Not sure which package fits? Tell us about your event and the venue will work with you to build the right experience from scratch.

What's typically included

  • Space & layout
  • Food & beverage
  • AV & technology

Venue Details

Standout features

Historic Setting
137-year-old inn with vintage cottages
A resort colony featuring a historic inn and seven charming vintage cottages with granite fireplaces and classic Maine decor, offering a unique blend of history and comfort.
Natural Surroundings
60 acres with ocean views and private beaches
Located on Eggemoggin Reach with views of Pumpkin Island and Deer Isle Bridge, the property includes private beaches, onsite hiking trails, and direct access to Penobscot Bay for a serene waterfront experience.
Event Spaces
Versatile venues for weddings and retreats
Features include oak grove ceremony sites, a large barn with granite fireplace and high rafters, and a communal guest house with a broad porch and full kitchen, supporting a range of private events and group gatherings.

At a glance

Rated 4.7 on Google · 91 reviews