Great Diamond Island Ski Vacations

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Top Ski vacation packages in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was ￥427,683, price is now ￥366,786 per person
￥366,786
per person
May 20 - May 26
found 15 hours ago
Roundtrip flight included
Osaka (OSA) to Portland (PWM)
9.4/10 Exceptional! (684 reviews)
Parking is great and very convenient. Staff is very friendly. Breakfast was delicious. I do think our room could use more light. Door numbers of the rooms could be bigger. The hallway is dark making it difficult to read the numbers.

Reviewed on Mar 2, 2026

Grasshopper Inn

Grasshopper Inn

4 out of 5
Price was ￥420,118, price is now ￥369,040 per person
￥369,040
per person
May 20 - May 26
found 15 hours ago
Roundtrip flight included
Osaka (OSA) to Portland (PWM)
9.8/10 Exceptional! (71 reviews)
We had a fantastic stay at Grasshopper Inn and will definitely return when back in the area. Clean, friendly staff and brilliant location.

Reviewed on Oct 22, 2025

Stage Neck Inn

Stage Neck Inn

4 out of 5
Price was ￥427,254, price is now ￥399,156 per person
￥399,156
per person
May 20 - May 26
found 15 hours ago
Roundtrip flight included
Osaka (OSA) to Portland (PWM)
9.4/10 Exceptional! (517 reviews)
We loved our stay it was just perfect

Reviewed on Jan 2, 2026

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