
Plum Island Ski Vacations
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Top Ski vacation packages in Plum Island
Price found within the past 48 hours. Click for updated prices.


Boston Harbor Hotel
North End
Save 100% on your flight
Price was ¥176,582, price is now ¥112,183 per person
¥112,183
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Hotel is beautiful with great views. You can expect to hear racing cars on Saturday nights.
We put in a handicap room that water could not be contained in the shower area. Expedia guest seemed to be treated as less desirable guests.
Reviewed on Sep 29, 2025

The Whitney Hotel
Beacon Hill
Save 100% on your flight
Price was ¥174,238, price is now ¥113,506 per person
¥113,506
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
The room was clean, the staff was great and the hotel is in a great area of the city. Loved our stay.
Reviewed on Sep 27, 2025

The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was ¥168,842, price is now ¥113,252 per person
¥113,252
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
This is the first time we have stayed at this property. The location, accommodations and staff were fantastic. I was especially impressed by the customer service provided by the staff. Every staff member greeted us personally, asked if we needed anything and invariably wished us a good day. The staff alone made our stay a pleasure-able experience.
Reviewed on Sep 17, 2025

Battery Wharf Hotel, Boston Waterfront
North End
Save 100% on your flight
Price was ¥118,532, price is now ¥86,536 per person
¥86,536
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (1,656 reviews)
Only draw back was the sounds of ship horns in the wee hours. Staff were lovely, location was convenient to the North End and a quick ride to the airport. Would totally stay again.
Reviewed on Sep 25, 2025
5* Ski vacations in Plum Island
Price found within the past 48 hours. Click for updated prices.

Boston Harbor Hotel
North End
Save 100% on your flight
Price was ¥176,582, price is now ¥112,183 per person
¥112,183
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Hotel is beautiful with great views. You can expect to hear racing cars on Saturday nights.
We put in a handicap room that water could not be contained in the shower area. Expedia guest seemed to be treated as less desirable guests.
Reviewed on Sep 29, 2025

The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was ¥168,842, price is now ¥113,252 per person
¥113,252
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
This is the first time we have stayed at this property. The location, accommodations and staff were fantastic. I was especially impressed by the customer service provided by the staff. Every staff member greeted us personally, asked if we needed anything and invariably wished us a good day. The staff alone made our stay a pleasure-able experience.
Reviewed on Sep 17, 2025

Raffles Boston
Back Bay
Price was ¥309,070, price is now ¥244,580 per person
¥244,580
per person
Nov 20 - Nov 23
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back!
Reviewed on Sep 15, 2025
3 Night Ski vacations in Plum Island
Price found within the past 48 hours. Click for updated prices.

Boston Harbor Hotel
North End
Save 100% on your flight
Price was ¥176,582, price is now ¥112,183 per person
¥112,183
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Hotel is beautiful with great views. You can expect to hear racing cars on Saturday nights.
We put in a handicap room that water could not be contained in the shower area. Expedia guest seemed to be treated as less desirable guests.
Reviewed on Sep 29, 2025

The Whitney Hotel
Beacon Hill
Save 100% on your flight
Price was ¥174,238, price is now ¥113,506 per person
¥113,506
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
The room was clean, the staff was great and the hotel is in a great area of the city. Loved our stay.
Reviewed on Sep 27, 2025

The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was ¥168,842, price is now ¥113,252 per person
¥113,252
per person
Nov 20 - Nov 23
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
This is the first time we have stayed at this property. The location, accommodations and staff were fantastic. I was especially impressed by the customer service provided by the staff. Every staff member greeted us personally, asked if we needed anything and invariably wished us a good day. The staff alone made our stay a pleasure-able experience.
Reviewed on Sep 17, 2025
4 Night Ski vacations in Plum Island
Price found within the past 48 hours. Click for updated prices.

The Whitney Hotel
Beacon Hill
Price was ¥920,712, price is now ¥824,228 per person
¥824,228
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
The room was clean, the staff was great and the hotel is in a great area of the city. Loved our stay.
Reviewed on Sep 27, 2025

Boston Harbor Hotel
North End
Price was ¥1,023,496, price is now ¥826,534 per person
¥826,534
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Hotel is beautiful with great views. You can expect to hear racing cars on Saturday nights.
We put in a handicap room that water could not be contained in the shower area. Expedia guest seemed to be treated as less desirable guests.
Reviewed on Sep 29, 2025

Raffles Boston
Back Bay
Price was ¥977,461, price is now ¥840,046 per person
¥840,046
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back!
Reviewed on Sep 15, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.