Vacation Pirate - Vacation Rentals in Downtown Skagway

Apartment Dolphin House From US $212
         

10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Hunter's Haven From US $124
         

9.7 (18 Reviews)
House
  • Parking
  • TV
  • View
At the White House From US $225
         

9.8 (250 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Spacious Home in Skagway Alaska From US $513
         

9.8 (27 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Cabin 2 Lynn View Lodge From US $218
         

9.8 (9 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Suite one bedroom with loft. From US $188
         

9.6 (5 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Suite 2 Lynn View Lodge From US $250
         

9.6 (4 Reviews)
Condo
  • Parking
  • Pet Friendly
  • TV
Front Room Lynnview Lodge From US $190
         

9.4 (16 Reviews)
Condo
  • Parking
  • Pet Friendly
  • TV

Luxury Places to Stay in Downtown Skagway

Over 49+ Luxury Places to Stay in or Near Downtown Skagway
Dolphin House From US $776
         

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9.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Transportation/Shuttle
Dolphin House From US $532
         

9.4 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Apartment Dolphin House From US $345
         

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7.7 (4 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • View
Gorgeous Chilkat Tower #3, 2BR Condo, downtown From US $339
         

10.0 (17 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
Gorgeous Chilkat Tower #2 2BR Condo, downtown From US $328
         

10.0 (8 Reviews)
Condo
  • Parking
  • Pet Friendly
  • TV

Top-Rated Vacation Rentals with a Pool in Downtown Skagway

Over 2+ Top-Rated Vacation Rentals with a Pool in or Near Downtown Skagway
Captain's Choice Motel From US $195
         

9.2 (244 Reviews)
Hotel
  • Parking
  • Pool
  • TV

Pet-Friendly Vacation Rentals in Downtown Skagway

Over 15+ Pet-Friendly Vacation Rentals in or Near Downtown Skagway
Cabin 1 Lynn View Lodge From US $215
         

9.0 (11 Reviews)
Condo
  • Parking
  • Pet Friendly
  • TV
Cabin 2 Lynn View Lodge From US $230
         

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9.1 (17 Reviews)
House
  • Parking
  • Pet Friendly
  • Transportation/Shuttle
Cabin 3 Lynn View Lodge From US $218
         

8.8 (9 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Front Room Lynnview Lodge From US $230
         

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9.0 (27 Reviews)
House
  • Parking
  • Pet Friendly
  • Transportation/Shuttle
Gorgeous Chilkat Tower #1, 2BR Condo, downtown From US $316
         

10.0 (21 Reviews)
Condo
  • Parking
  • Pet Friendly
  • TV
Cabin 1 Lynn View Lodge From US $230
         

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8.7 (25 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Mountain Glacier View Surrounded by Habitat From US $206
         

9.6 (10 Reviews)
Ski Chalet
  • Parking
  • Pet Friendly
  • View
Skagway Cottage Dog Friendly From US $225
         

New
House
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens

Large Vacation Homes & Villas in Downtown Skagway

Over 2+ Large Vacation Homes & Villas in or Near Downtown Skagway
Beach Roadhouse From US $135
         

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9.4 (112 Reviews)
Cabin
  • Parking
  • View
  • Wheelchair Accessible
Historic Skagway Inn From US $197
         

8.6 (172 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • View

Wheelchair Accessible Vacation Homes in Downtown Skagway

Over 3+ Wheelchair Accessible Vacation Homes in or Near Downtown Skagway
Aspen Suites Hotel Haines From US $179
         

8.7 (114 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Aspen Suites Hotel Haines From US $185
         

9.4 (335 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Holland America Skagway Inn From US $276
         

8.2 (277 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Wheelchair Accessible

Downtown Skagway Varoom and Airbnb Places to Stay Under $200

Over 8+ Downtown Skagway Varoom and Airbnb Places to Stay Under $200
Accommodation at Chilkat bakery From US $172
         

10.0 (12 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Beachroadhouse From US $198
         

9.8 (42 Reviews)
Cabin
  • Parking
  • TV
  • Balcony/Terrace
Suites at the Bakery From US $179
         

9.8 (8 Reviews)
House
  • Security/Safety
  • Child Friendly
  • Internet
Hotel Halsingland From US $174
         

8.6 (430 Reviews)
Hotel
  • Parking
  • TV
  • Balcony/Terrace
Sweet one bedroom at the bakery From US $199
         

9.8 (7 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace
Scenic studio From US $129
         

New
Apartment
  • Parking
  • TV
  • Bedding/Linens

Instantly Bookable Vacation Homes in Downtown Skagway

Over 2+ Instantly Bookable Vacation Homes in or Near Downtown Skagway

About Downtown Skagway Vacation Rentals

With more than 58 Downtown Skagway vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Vacationpirate and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Downtown Skagway.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Vacationpirate Downtown Skagway, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Downtown Skagway. Places to stay near Downtown Skagway are 243.66 ft² on average, with prices averaging $263 a night.

Vacationpirate makes it easy and safe to find and compare vacation rentals in Downtown Skagway with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Downtown Skagway

Type Count
Vacation Homes 22
Hotels with Suites 12
Holiday Apartments 5
Cabin Rentals 5
Cottages 5
B&B 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Downtown Skagway

Pro Tip: Vacationpirate makes it easy to compare the best listings on Vacationpirate homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Vacationpirate homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Downtown Skagway.

Weather in Downtown Skagway

View the weather forecast for Downtown Skagway before booking your Downtown Skagway Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F