Southeast Massachusetts Vacation Packages
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Top Southeast Massachusetts vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Josiah Keith House
9.8/10 Exceptional! (37 reviews)
Oct 8 - Oct 11
3 night stay
Chicago (CHI) to Boston (BOS)
Southwest Airlines • Coach
Boston (BOS) to Chicago (CHI)
JetBlue Airways • Coach
Price was $573, price is now $421 per person
$421
per person
found 1 day ago
This unique historic property was a delight to visit. Justin our host was incredibly passionate about the history of the house and the area. He was also very welcoming and cooked an incredible breakfast. If you are interested in Massachusetts and/or early American history and want a stay with a difference I would thoroughly recommend Josiah Keith House.
Reviewed on Jun 26, 2026
3.5-star property
By the Sea Guests Bed & Breakfast & Suites
9.4/10 Exceptional! (195 reviews)
Sep 18 - Sep 21
3 night stay
Chicago (CHI) to Boston (BOS)
JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $709, price is now $493 per person
$493
per person
found 1 day ago
The property was well maintained and close to good restaurants. We had a cooked breakfast every day.
Reviewed on Jul 16, 2026
2.0-star property
Pier 7 Condominiums
Bass River
9/10 Wonderful! (9 reviews)
Aug 25 - Aug 28
3 night stay
Chicago (CHI) to Boston (BOS)
JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $678, price is now $475 per person
$475
per person
found 1 day ago
The room was clean, I loved the kitchenette! The area was nice!
Reviewed on Jul 13, 2026
3.0-star property
The Cove at Yarmouth by Westgate Resorts
9.2/10 Wonderful! (268 reviews)
Sep 18 - Sep 21
3 night stay
Chicago (CHI) to Boston (BOS)
JetBlue Airways • Non-stop roundtrip • Coach
Price was $672, price is now $495 per person
$495
per person
found 11 hours ago
P
Indoor pool and hot tub loved and the outdoor Shack was great
Reviewed on Jun 8, 2026
Top rated hotels for your Southeast Massachusetts vacation package
Best Western Adams Inn Quincy-Boston
29 Hancock St Quincy MA
Free Cancellation
Reserve now, pay when you stay
44.65 mi from city center
$161 nightly
The price is $180 total per night
$180 total
Jul 26 - Jul 27
Total with taxes and fees
Best Western Adams Inn Quincy-Boston features a gym, free WiFi in public areas, and meeting rooms. Self parking is available for USD 10 per night. The 24-hour front desk has multilingual staff ready to assist with concierge services and securing valuables. Additional amenities include conference space, express check-in, and express check-out.
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Free Cancellation
Reserve now, pay when you stay
13.63 mi from city center
$306 nightly
The price is $351 total per night
$351 total
Aug 6 - Aug 7
Total with taxes and fees
Guests of Margaritaville Resort Cape Cod have access to a full-service spa, a water park, and an indoor pool. Free parking is available if you drive. The 24-hour front desk has staff standing by to help with access to locker space, dry cleaning/laundry, and securing valuables. Other amenities at this spa resort include an outdoor pool, a lazy river, and a children's pool.
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Free Cancellation
Reserve now, pay when you stay
12.92 mi from city center
$218 nightly
The price is $249 total per night
$249 total
Jul 19 - Jul 20
Total with taxes and fees
At Iris Hotel Cape Cod , guests enjoy an indoor pool, a gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has staff standing by to help with securing valuables and luggage storage. Additional amenities include conference space, a business center, and coffee/tea in a common area.
Pool
Parking included
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View all propertiesLowest 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.
Things to do
Moby Dick's New Bedford Smartphone Guided Walking Tour
$8
per adult
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