Holiday rentals in Skagway Municipality

KerryRating, 5 stars1 week ago

Studio Apartment in Historic Skagway

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.

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!!!

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.

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!

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.

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!

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 🙏😊

4.89 out of 5 average rating, 91 reviews

Private room in Skagway

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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Other great holiday rentals in Skagway Municipality

4.89 out of 5 average rating, 91 reviews

Private room in Skagway

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!

4.85 out of 5 average rating, 78 reviews

Private room in Skagway

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.

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.

KerryRating, 5 stars1 week ago

Studio Apartment in Historic Skagway

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.

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!

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!

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.