Eastern Massachusetts Adventure Vacations
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Top Adventure vacation packages in Eastern Massachusetts
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was ￥606,232, price is now ￥332,338 per person
￥332,338
per person
Dec 4 - Dec 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
The Boston Harbor Hotel is absolutely gorgeous! The staff are extremely polite, professional and always happy to help!
Our room was beautiful and the views of the harbor were great! Loved the location being walkable to so many great spots! Would absolutely stay here again!
Reviewed on Sep 29, 2025
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was ￥167,994, price is now ￥112,736 per person
￥112,736
per person
Nov 20 - Nov 23
found 20 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 1 day 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
Hotel Commonwealth
Fenway–Kenmore
Save 100% on your flight
Price was ￥116,570, price is now ￥89,172 per person
￥89,172
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.4/10 Exceptional! (1,748 reviews)
Beautiful hotel, great veiws, clean rooms, freimdly amd accommodating staff, amd perfect location for a game
Reviewed on Sep 27, 2025
Don't see what you're looking for?
See all available trips from Chicago to Eastern Massachusetts
View all trips5* Adventure vacations in Eastern Massachusetts
Price found within the past 48 hours. Click for updated prices.
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was ￥167,994, price is now ￥112,736 per person
￥112,736
per person
Nov 20 - Nov 23
found 20 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
Boston Harbor Hotel
North End
Save 100% on your flight
Price was ￥606,232, price is now ￥332,338 per person
￥332,338
per person
Dec 4 - Dec 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
The Boston Harbor Hotel is absolutely gorgeous! The staff are extremely polite, professional and always happy to help!
Our room was beautiful and the views of the harbor were great! Loved the location being walkable to so many great spots! Would absolutely stay here again!
Reviewed on Sep 29, 2025
Don't see what you're looking for?
See all available trips from Chicago to Eastern Massachusetts
View all trips3 Night Adventure vacations in Eastern Massachusetts
Price found within the past 48 hours. Click for updated prices.
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 1 day 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
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 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
The Boston Harbor Hotel is absolutely gorgeous! The staff are extremely polite, professional and always happy to help!
Our room was beautiful and the views of the harbor were great! Loved the location being walkable to so many great spots! Would absolutely stay here again!
Reviewed on Sep 29, 2025
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was ￥167,994, price is now ￥112,736 per person
￥112,736
per person
Nov 20 - Nov 23
found 20 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
Don't see what you're looking for?
See all available trips from Chicago to Eastern Massachusetts
View all trips4 Night Adventure vacations in Eastern Massachusetts
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was ￥275,371, price is now ￥192,150 per person
￥192,150
per person
Nov 20 - Nov 24
found 9 hours ago
Roundtrip non-stop flight included
Frankfurt (FRA) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
The Boston Harbor Hotel is absolutely gorgeous! The staff are extremely polite, professional and always happy to help!
Our room was beautiful and the views of the harbor were great! Loved the location being walkable to so many great spots! Would absolutely stay here again!
Reviewed on Sep 29, 2025
Battery Wharf Hotel, Boston Waterfront
North End
Price was ￥191,860, price is now ￥153,468 per person
￥153,468
per person
Nov 20 - Nov 24
found 9 hours ago
Roundtrip non-stop flight included
Frankfurt (FRA) 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
Don't see what you're looking for?
See all available trips from Frankfurt to Eastern Massachusetts
View all tripsTop Adventure Eastern Massachusetts Hotels
HI Boston - Hostel
19 Stuart Street, Boston, MA
Stay at this hostel in Boston. Enjoy free WiFi, a 24-hour front desk, and a fireplace in the lobby. Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,004 reviews)
"My first time staying in a hostel in US was fantastic. The staff was welcoming, friendly and helpful. There are some activities planned everyday. Managed to join the yoga glass at Boston Common. Love it so much! Hope to come back again!"
Reviewed on Sep 24, 2025
Seaport Hotel Boston
1 Seaport Lane, Boston, MA
Stay at this 4-star eco-certified hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
9.6/10 Exceptional! (3,508 reviews)
"Great Seaport hotel."
Reviewed on Sep 30, 2025
Hilton Boston Park Plaza
50 Park Plaza, Boston, MA
Stay at this 4-star luxury hotel in Boston. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
8.2/10 Very Good! (3,190 reviews)
"Hotel staff were great. Unfortunately I booked through Expedia and they would not, give a refund. Hotel changed dates and camceled dates. Unfortunately hotel did not have the top tier room on the dates I needed, even after talking to them. I.checked expedia and they had room at same rate and the.dates.i ..."
Reviewed on Sep 29, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
