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Liveaboard M/V Sound Judgment - comes w minivan

Experience a fishermen's view of Sitka aboard the M/V Sound Judgment. Nestled into Thompson-Eliason Harbor, the nation's 9th most prolific fishing port, a stay aboard Sound Judgement offers you an authentic experience of the docks in romantic Sitka-by-the-Sea. The boat offers an on-board head and full kitchen, two berths that sleep up to four adults, city water and electric, and beautiful wood and brass finishes. A Chevy Compass minivan can be left at airport and will be yours for the stay.

Historic Alaskan Downtown Home | Walk Everywhere

Built in 1948, this warm home in the heart of downtown is the perfect base camp for Alaska's most extraordinary small city. Walk out the front door and you're minutes from the harbor, Sitka National Historical Park, St. Michael's Cathedral, Castle Hill, restaurants, and the brewery. The ocean is a five-minute walk. Inside, wood-paneled walls, a 100-year-old spruce live edge table, and local artwork give the space genuine Alaska character. Updated kitchen, cozy upstairs, natural light.

HarborView Cottage - new Subaru, p-boards, kayaks

A stone's throw away from Sitka's most picturesque harbor, this classic Sitka seaside home is perfect for a family wishing to be downtown, or near the harbor for fishing and whale-watching excursions. At night you can hear the buoys out on the water, and during the day see a bald eagle that nests across the street. Pick raspberries and salmonberries in our garden. Borrow the kayaks or take the bikes out for a spin! The place comes with an Infiniti SUV that can be left at the airport.

Tongass Cozy Cottage:Downtown (Car Rental Option)

Remodeled downtown bungalow within walking distance to all Sitka amenities such as downtown shops and businesses, grocery store and market, parks, trails, Sheldon Jackson Campus, University of Alaska, Sitka Community Hospital and SEARHC Hospital. This property has 4 dedicated bikes for guest use only. Helmets and bike locks included. Optional car rental for those finding Sitka's summer car rental prices & availability challenging. Please ask the property manager for more details.

Stowaway-free 4x4 4Runner, p-boards, kayaks, bikes

Nestled in the seaside corner of our historic home, this apartment lives up to its name - a quaint, private hideaway that comes with a dedicated 2023 TRD 4Runner, paddleboards, kayaks and bikes. Renovated in 2025, the apartment is in the center of town, just up from Crescent Harbor. With its hidden entrance, and maritime-themed furnishings, and infrared sauna, the apartment has the feel of a dockside Speakeasy. Great for folks wanting to get away from it all!

Studio 111 - 3rd floor

Amazing third floor views of the Pacific Ocean. Located 3.5 miles from downtown. The 111 Studio is perfect for your Sitka, Alaska stay. The 3rd floor space does NOT have a full kitchen. It does have a mini fridge, microwave, toaster oven, electric tea kettle and coffee pot. The space is private, accessed by an outside staircase in left side of house. Host is not responsible for snow removal in driveway or stairs, if such weather presents.

Beachfront Stay!

Make memories at this private beach retreat on Sitka’s sandy shore. Step onto your own beach, hear the tide roll in, and watch island views. Relax, explore, or reconnect in this peaceful marine-inspired escape. Enjoy water views, seaside strolls, and sunsets behind Mt. Edgecumbe. Ideal for a quiet beach experience with easy access to waterfront walks and natural beauty.

The Red Cottage Inn

🏡 Welcome to The Red Cottage Inn Tucked in a charming and walkable neighborhood just minutes from downtown Sitka, The Red Cottage Inn is your cozy home base for adventure, rest, and connection. With 3 bedrooms and room to comfortably sleep up to 6 guests, this space is ideal for families and groups looking to explore Southeast Alaska in comfort and style.

Cottages on Monastery, Unit 2

Welcome to Cottages on Monastery, your serene getaway located in the heart of downtown Sitka. These charming cottages are perfect for singles, couples, or large groups looking to enjoy individual rentals close to one another. Whether you’re exploring Sitka’s attractions or simply relaxing, these cottages offer a peaceful and quiet retreat.

Cottages on Monastery, Unit 3

Welcome to Cottages on Monastery, your serene getaway located in the heart of downtown Sitka. These charming cottages are perfect for singles, couples, or large groups looking to enjoy individual rentals close to one another. Whether you’re exploring Sitka’s attractions or simply relaxing, these cottages offer a peaceful and quiet retreat.

Edgecumbe Inn

Local family owned and operated rental in a quiet neighborhood. Close to downtown Sitka and within walking distance to nearby grocery store. Open floor plan for kitchen/dining area and living room. Large bedrooms with flexible bedding options and large closets. Ground floor access with a large covered deck area and partial water view.

Downtown Guest Suite

Keep it simple at this peaceful and centrally-located place. Within walking distance of all major attractions, this guest suite is perfect for the single traveler or couple. From thoughtful amenities to laundry access, this suite was created with the traveler in mind.