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Vacation rentals in Skagway Municipality

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Top-rated vacation rentals in Skagway Municipality

Guests agree: these stays are highly rated for location, cleanliness, and more.

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A scenic view showcases snow-capped mountains towering in the background, while a charming town unfolds below. Wooden benches are positioned on a deck, offering a vantage point for enjoying the surrounding landscapes. Power lines and buildings populate the view, defining the locale's character.

Apartment in Skagway

Studio Apartment in Historic Skagway

KerryRating, 5 stars1 week ago

Loved this place. We have stayed at quite a few Skagway Air B n Bs over the years and this was by far our favorite. It’s bigger than expected and I don’t think the photos do it justice. It was very well appointed, comfortable, quiet, and close to everything. Our host was great. We would love to stay here again.

A clean and organized bathroom features a white toilet and a modern gray vanity with a sink. Above the vanity, a mirror is mounted on the wall, complemented by a black metal storage rack holding towels. Soft lighting enhances the neutral decor.

Home in Skagway

4.68 out of 5 average rating, 19 reviews

MountainView Cottage

LisaRating, 5 stars1 month ago

Janilyn's place is amazing. There is a beautiful kitchen with a gas stove, large refrigerator and all the cooking necessities. The upstairs bedroom has it's own heater, sitting area and with a huge newly renovated bathroom. The location is peaceful and walking distance to town. We really enjoy our stay!!!

A colorful sign for 'The LILY PAD' features a playful frog holding an acorn while parachuting. Surrounding elements include bright flowers and green foliage, creating a cheerful and inviting visual entrance to the property.

Home in Skagway

5 out of 5 average rating, 9 reviews

Skagway Lily Pad/ Downstairs is all yours!

KrisRating, 5 stars46 months ago

Convenient location in Skagway, easy to walk to from the ferry. Excellent base for exploring the area’s outdoor offerings. Glacial Coffeehouse, StarFire & Skagway Fish Company & Skagway Museum were great places to visit. Becky’s house has everything you might need to have a warm & welcoming stay.

A window reveals a stunning view of majestic mountains, bathed in natural light. The scene features clear blue skies and snow-capped peaks. The window frame is minimalist, and the interior includes part of a colorful blanket at the bottom, adding a cozy touch.

Apartment in Skagway

5 out of 5 average rating, 42 reviews

Midtown Skagway (Upstairs Apartment)

EvanRating, 5 stars1 month ago

Place was GREAT! Stayed there on a work trip for nine days. Place is located far enough away from Broadway St. you don't feel like you are in the middle of everything and it's close enough to get to everything. Easy to get out to Dyea too. Place is comfortable and a great place to stay for work or travel. This is our second time staying here - we will definitely be back!

A view from the studio apartment showcases a vibrant blue building bordered by green foliage. The distant mountains rise against a backdrop of partially cloudy sky, with a mix of lush greenery and occasional residential structures visible along the street.

Apartment in Skagway

5 out of 5 average rating, 57 reviews

Skagway Studio Suite

DebRating, 5 stars3 weeks ago

Tom and Vickey were extremely flexible with my check in and check out. Clear and useful reminders/ instructions inside. The place is very comfortable and cozy, great for 2 people. Very walkable to downtown area and hiking in Skagway. After 4 days in the car, it was a great little place to recover. Quiet street.

A private outdoor deck is visible, bordered by wooden railing and lattice. Dense green foliage envelops the surroundings, with glimpses of distant mountains in the background. A roofed area can be seen to the left, suggesting additional outdoor space.

Apartment in Skagway

4.93 out of 5 average rating, 43 reviews

Hilltop Hideaway

WalkerRating, 5 stars1 week ago

Was very satisfied with the stay! Was a little off the beaten path which lent itself to some quieter evenings and a more private feel. Easy access for our car. Super clear instructions on every level, and the owner gave us some sweet local hiking recommendations. Me and my wife loved it! A great place to stay if you find yourself in Skagway for a time! Thanks Dylan!

A modern tiny home is surrounded by a landscaped yard featuring a stone pathway. Two pink Adirondack chairs are positioned outside, inviting relaxation. The home showcases large windows and a distinct roofline, with evergreen trees framing the scene against a partly cloudy sky.

Tiny home in Skagway

5 out of 5 average rating, 3 reviews

Cozy downtown tiny home

JulesRating, 5 stars14 months ago

Nicely done tiny home in a good central location in Skagway which really makes the most of the space. Bed was comfy, the shower hot and the place kept nice and warm. If felt very safe to stay here too. Not too much happening in Skagway this time of year but it was very quick and easy to get to everything from Meredith’s place. Thank you for the stay 🙏😊

A wooden fence displays a mural featuring vibrant flowers and greenery. A sign reading 'At the Lily Pad' is positioned prominently above a planter containing various plants and flowers, contributing to a cheerful and inviting garden setting.

Private room in Skagway

4.89 out of 5 average rating, 91 reviews

Skagway Lily Pad/ Lupine Room/no pets

SkylarRating, 5 stars1 month ago

The Lily Pad is a great spot to stay in Skagway! It had everything we might need, and the beds were made with cozy, beautiful quilts. I could tell Becky has put a lot of time and intentionality into the Lily Pad. I would stay here again and recommend it!

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Popular amenities for Skagway Municipality vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Skagway Municipality

A wooden fence displays a mural featuring vibrant flowers and greenery. A sign reading 'At the Lily Pad' is positioned prominently above a planter containing various plants and flowers, contributing to a cheerful and inviting garden setting.

Private room in Skagway

4.89 out of 5 average rating, 91 reviews

Skagway Lily Pad/ Lupine Room/no pets

SkylarRating, 5 stars1 month ago

The Lily Pad is a great spot to stay in Skagway! It had everything we might need, and the beds were made with cozy, beautiful quilts. I could tell Becky has put a lot of time and intentionality into the Lily Pad. I would stay here again and recommend it!

A wooden fence displays a decorative sign reading 'At The Lily Pad.' Colorful flowers and lush greenery surround the sign, enhancing the garden's vibrant ambiance. Various blooming plants, including geraniums and lupines, are arranged in a galvanized planter, contributing to a charming outdoor setting.

Private room in Skagway

4.85 out of 5 average rating, 78 reviews

Skagway Lily Pad/ The Lily Room/ no pets

MarilynRating, 5 stars1 month ago

The LilyPad is a delightful spot; cozy, peaceful, comfortable and perfect for my needs.

A modern kitchen space features white cabinetry and countertops, complemented by dark wood accents. A wood dining table with two high stools is positioned at the center. Natural light illuminates the area through a large window, which overlooks greenery outside.

Apartment in Skagway

4.88 out of 5 average rating, 32 reviews

Midtown Skagway (Downstairs Apartment )

RichardRating, 5 stars1 month ago

We have a project in the spring of 2026 and hope to stay here again if Juliene will have us.

A scenic view showcases snow-capped mountains towering in the background, while a charming town unfolds below. Wooden benches are positioned on a deck, offering a vantage point for enjoying the surrounding landscapes. Power lines and buildings populate the view, defining the locale's character.

Apartment in Skagway

Studio Apartment in Historic Skagway

KerryRating, 5 stars1 week ago

Loved this place. We have stayed at quite a few Skagway Air B n Bs over the years and this was by far our favorite. It’s bigger than expected and I don’t think the photos do it justice. It was very well appointed, comfortable, quiet, and close to everything. Our host was great. We would love to stay here again.

An outdoor eating area is featured on a wooden deck, surrounded by lattice panels and vibrant flower pots. A round table is accompanied by six chairs, and a red umbrella offers shade. Scenic mountain views are visible in the background.

Home in Skagway

4.88 out of 5 average rating, 67 reviews

Skagway State Street/Main Floor 3 Bedroom House

DawnRating, 5 stars2 months ago

Thank you so much for a wonderful stay Katherine! We truly enjoyed our visit in Skagway. Clean, comfortable and quiet! Would highly recommend a stay in this beautiful house and location!

A window reveals a stunning view of majestic mountains, bathed in natural light. The scene features clear blue skies and snow-capped peaks. The window frame is minimalist, and the interior includes part of a colorful blanket at the bottom, adding a cozy touch.

Apartment in Skagway

5 out of 5 average rating, 42 reviews

Midtown Skagway (Upstairs Apartment)

EvanRating, 5 stars1 month ago

Place was GREAT! Stayed there on a work trip for nine days. Place is located far enough away from Broadway St. you don't feel like you are in the middle of everything and it's close enough to get to everything. Easy to get out to Dyea too. Place is comfortable and a great place to stay for work or travel. This is our second time staying here - we will definitely be back!

A view from the studio apartment showcases a vibrant blue building bordered by green foliage. The distant mountains rise against a backdrop of partially cloudy sky, with a mix of lush greenery and occasional residential structures visible along the street.

Apartment in Skagway

5 out of 5 average rating, 57 reviews

Skagway Studio Suite

DebRating, 5 stars3 weeks ago

Tom and Vickey were extremely flexible with my check in and check out. Clear and useful reminders/ instructions inside. The place is very comfortable and cozy, great for 2 people. Very walkable to downtown area and hiking in Skagway. After 4 days in the car, it was a great little place to recover. Quiet street.

A colorful sign for 'The LILY PAD' features a playful frog holding an acorn while parachuting. Surrounding elements include bright flowers and green foliage, creating a cheerful and inviting visual entrance to the property.

Home in Skagway

5 out of 5 average rating, 9 reviews

Skagway Lily Pad/ Downstairs is all yours!

KrisRating, 5 stars46 months ago

Convenient location in Skagway, easy to walk to from the ferry. Excellent base for exploring the area’s outdoor offerings. Glacial Coffeehouse, StarFire & Skagway Fish Company & Skagway Museum were great places to visit. Becky’s house has everything you might need to have a warm & welcoming stay.

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