Vacation rentals in Skagway

Rainbow Country Lodge Ocean Front w/ Glacier Views

The views from this 2800 sq. foot home in Haines, AK are sure to impress the most well traveled explorer. Eagles, whales, sea lions, & moose are seen occasionally. Whether you're a single family, several families, or group of friends, this home is well suited to fit your needs. The yard has a fire pit, treehouse, & lawn chairs. A perfect place, 12 minutes from town, to spread out & enjoy vacation. A charge of $100 per guest after 5 guests will apply per night. Hot tub is no longer available

Front Street #1 Waterfront, View, 2BR, 2Bath

Enjoy front-row views of Alaska’s natural beauty while staying right in the center of it all—this inviting condo blends scenery, comfort, and walkable convenience. Nestled along the shores of the spectacular Lynn Canal, Front Street Condos is located just one block from the boat harbor and within easy walking distance to downtown, making this an ideal home base for exploring. Designed with travelers in mind, each condo is bright, airy, and spacious—perfect for families, couples, or friends.

The Chilkoot Cottage: Bear Viewing & Fishing

This quiet and cozy 2-bedroom cottage is located 10 miles from Haines near the famous Chilkoot River, where bears and eagles congregate. Enjoy sweeping views of Lutak Inlet and the beach where bears and eagles may be seen. Chilkoot River and Lake are just down the road and offer fishing for salmon and world-famous bear viewing. The house is fully furnished and feels like a real Alaskan home. Chilkoot Cottage is truly the best location in Haines to enjoy a real Alaskan experience.

Forget Me Not Cabin @ The Swaying Spruce

Escape to the cozy Forget-Me-Not Cabin, a charming log cabin perfect for 1–2 guests. Enjoy a queen bed, private bathroom, wood stove, electric heat, refrigerator, microwave, toaster, coffee maker, and complimentary coffee and tea. Nestled among the trees with mountain views nearby, it's a peaceful Skagway retreat. Traveling with friends or family? The Columbine Cabin is just a 50-foot walk away, making it easy to accommodate larger groups together.

Little Alaskan Lodge

Relax with the whole family at this peaceful retreat designed with children in mind. Located within walking distance to town and the beach. Activities abound around the property for all ages. Whether you need a place to rest and enjoy a peaceful view, celebrate the bounty of the Alaskan life, or appreciate a unique home for littles to enjoy, our home is your home while you stay at The Little Alaskan Lodge.

Modern 2-Bedroom Skagway Escape • King + Queen Bed

New, modern 2-bedroom guesthouse designed for a comfortable Skagway stay. Enjoy a fully equipped, well-appointed kitchen, in-unit washer/dryer, cozy modern finishes, and premium mattresses for restful nights after exploring town, the mountains, or the Yukon. A clean, private, and welcoming home base just minutes from Skagway’s shops, restaurants, and adventures.

The Cozy Rustic Cabin

Cozy Rustic Alaskan cabin retreat in beautiful Haines. This warm, wood-lined getaway features 2 comfortable bedrooms, a fully equipped kitchen, bathroom and a relaxing living space. Enjoy peaceful surroundings, natural light, and views of the forest and green landscape. Perfect for hiking, wildlife watching, or simply unwinding in quiet Alaskan charm.

Skagway Lily Pad/ 3 bedrooms

You are renting three bedrooms with a shared bath, living room and kitchen. You'll only be sharing with the others who you have in the three bedrooms. The location of the LilyPad is within a three block walking distance to Broadway and downtown. There are hiking trails and the Lynn Canal all within walking distance also.

Cozy Skagway Home

Older 3 bedroom home in Skagway, AK within walking distance to grocery store, restaurants, and hiking trails. You will have the main floor of the house and a porch with outdoor eating area that includes a grill and fire pit. The bottom floor is a separate apartment housing Pure Connection Massage Therapy, LMT.

The Nest

Our sunny little cottage sits 2.3 miles from town. There are many options for adventure just minutes away! Lots of beaches within walking distance of cottage. Wonderful trail system 1/2 mile away. Wake up to the sound of birds! Our place is good for couples, couples with small child and solo adventurers.

3 bedroom yurt with amazing view

Our cozy yurt overlooking the Chilkat River and mountains isn't your average yurt! It has 3 bedrooms, a bathroom, kitchen, loft space, and hot tub. We also provide wireless internet and direct TV. The yurt shares the property with our family home, 2 miles outside of scenic Haines, Alaska.

Midtown Skagway (Upstairs Apartment)

Located smack-dab in the middle of Skagway, you will be close to everything at this cozy apartment. Walking distance to all the fun "downtown" Skagway has to offer, yet nestled in the mid-town neighborhood offering mountain views and quiet escape.