Massachusetts Adventure Vacation Packages
Best Massachusetts Adventure packages
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Save 100% on your flight
Price was $1,008, price is now $671 per person
$671
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Nice staff, nice room and facilities. Having stayed there several times happily and will be back again in June. Thanks.
Reviewed on May 22, 2026
Fairmont Copley Plaza, Boston
Back Bay
Price was $1,124, price is now $820 per person
$820
per person
Jun 30 - Jul 3
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The food and hospitality was amazing!
Reviewed on Mar 28, 2026
Sea Crest Beach Resort
Price was $986, price is now $746 per person
$746
per person
Jun 1 - Jun 4
found 18 hours ago
Roundtrip flight included
Detroit (DTT) to Boston (BOS)
Book a stay at this beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Silver Beach and Cataumet Arts Center are located nearby.
5pm check in- ridiculous
18$ pool cocktails-ridiculous
Dirty beaches- extremely ridiculous
Mold in bathroom
25$ per night super uncomfortable rollaway bed- ridiculous
Reviewed on Aug 9, 2025
3 night Massachusetts Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Back Bay
Price was $1,124, price is now $820 per person
$820
per person
Jun 30 - Jul 3
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The food and hospitality was amazing!
Reviewed on Mar 28, 2026
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,788, price is now $1,053 per person
$1,053
per person
Jul 31 - Aug 3
found 10 hours ago
Roundtrip flight included
Columbus (CMH) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.
Reviewed on Mar 24, 2024
The Colonnade Hotel Back Bay
Back Bay
Price was $1,493, price is now $963 per person
$963
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
I loved that it was walking distances to Fenway Park. Andrew was very helpful and kind. Clean hotel. Highly recommend.
Reviewed on Aug 1, 2025
4 night Massachusetts Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Plymouth
Save 100% on your flight
Price was $963, price is now $716 per person
$716
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
Book a stay at this business-friendly hotel in Plymouth. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Plymouth Harbor and Jungleplex are located nearby.
This is the cleanest hotel we've stayed at in a long time. Staff was very professional and friendly.
Reviewed on Apr 5, 2025
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,267, price is now $1,274 per person
$1,274
per person
Jul 31 - Aug 4
found 10 hours ago
Roundtrip flight included
Columbus (CMH) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.
Reviewed on Mar 24, 2024
Green Harbor Resort
Price was $1,582, price is now $1,161 per person
$1,161
per person
Jun 7 - Jun 11
found 6 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this beach hotel in West Yarmouth. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
Beautiful resort. My kids and I loved it. Nice pool and beautiful views.
Reviewed on Jul 8, 2024
5 night Massachusetts Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Save 100% on your flight
Price was $781, price is now $498 per person
$498
per person
Jul 7 - Jul 12
found 22 hours ago
Roundtrip flight included
Cleveland (CLE) to Albany (ALB)
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Nice staff, nice room and facilities. Having stayed there several times happily and will be back again in June. Thanks.
Reviewed on May 22, 2026
Boston Harbor Hotel
North End
Price was $2,663, price is now $1,314 per person
$1,314
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.
Reviewed on Mar 24, 2024
Sea Crest Beach Resort
Save 100% on your flight
Price was $1,423, price is now $990 per person
$990
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Book a stay at this beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Silver Beach and Cataumet Arts Center are located nearby.
5pm check in- ridiculous
18$ pool cocktails-ridiculous
Dirty beaches- extremely ridiculous
Mold in bathroom
25$ per night super uncomfortable rollaway bed- ridiculous
Reviewed on Aug 9, 2025
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Save 100% on your flight
Price was $1,008, price is now $671 per person
$671
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Nice staff, nice room and facilities. Having stayed there several times happily and will be back again in June. Thanks.
Reviewed on May 22, 2026
The Godfrey Hotel Boston
Downtown Boston
Save 100% on your flight
Price was $1,483, price is now $962 per person
$962
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
Great place we always use when visiting Boston. Opens up next to George Howell Coffee which is always a treat. The staff are responsive, the rooms clean, and the location is excellent (next to Emerson, china town, the commons, newbury street, etc.).
Reviewed on May 15, 2026
Sea Crest Beach Resort
Save 100% on your flight
Price was $2,475, price is now $1,628 per person
$1,628
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
Book a stay at this beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Silver Beach and Cataumet Arts Center are located nearby.
5pm check in- ridiculous
18$ pool cocktails-ridiculous
Dirty beaches- extremely ridiculous
Mold in bathroom
25$ per night super uncomfortable rollaway bed- ridiculous
Reviewed on Aug 9, 2025
Adventure hotels in Massachusetts
HI Boston - Hostel
19 Stuart Street Boston MA
Free Cancellation
Reserve now, pay when you stay
$224 nightly
The price is $261 total per night
$261 total
Jun 7 - Jun 8
Total with taxes and fees
Guests of HI Boston - Hostel enjoy free WiFi in public areas, meeting rooms, and a library. Offsite parking is offered for a fee. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include express check-out, laundry facilities, and a water dispenser.
Free WiFi
Air conditioning
Seaport Hotel Boston
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
$236 nightly
The price is $274 total per night
$274 total
May 29 - May 30
Total with taxes and fees
Guests of Seaport Hotel Boston have access to an indoor pool, a gym, and a steam room. Valet parking is available for USD 59 per night. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and luggage storage. Additional amenities include free WiFi in public areas, meeting rooms, and a conference center.
Pool
Pet friendly
Hilton Boston Park Plaza
50 Park Plaza Boston MA
Free Cancellation
Reserve now, pay when you stay
$250 nightly
The price is $291 total per night
$291 total
May 31 - Jun 1
Total with taxes and fees
Guests of Hilton Boston Park Plaza enjoy a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 70 per day. The front desk has multilingual staff on hand 24/7 to help with concierge services, luggage storage, and dry cleaning/laundry. Other amenities at this luxury hotel include conference space, a 24-hour business center, and a computer station.
Pet friendly
Free WiFi
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.
How much does it cost to fly to Massachusetts?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
TPA
Tampa Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 21 hours ago
$142
Roundtrip
found 21 hours ago
TPA
Tampa Intl.
PVD
T.F. Green
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
MCO
Orlando Intl.
BOS
Logan Intl.
$168 Roundtrip, found 22 hours ago
$168
Roundtrip
found 22 hours ago
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$171 Roundtrip, found 3 days ago
$171
Roundtrip
found 3 days ago
MCO
Orlando Intl.
PVD
T.F. Green
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
MCO
Orlando Intl.
ALB
Albany Intl.
$182 Roundtrip, found 1 day ago
$182
Roundtrip
found 1 day ago
MCO
Orlando Intl.
ORH
Worcester Regional
$243 Roundtrip, found 3 days ago
$243
Roundtrip
found 3 days ago
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