Southeast Massachusetts Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Southeast Massachusetts vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
The Cove at Yarmouth by Westgate Resorts
9.2/10 Wonderful! (268 reviews)
Oct 22 - Oct 27
5 night stay
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $818, price is now $571 per person
$571
per person
found 1 day ago
P
Indoor pool and hot tub loved and the outdoor Shack was great
Reviewed on Jun 8, 2026
2.0-star property
The Cape Club Resort
9/10 Wonderful! (28 reviews)
Oct 22 - Oct 27
5 night stay
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $922, price is now $667 per person
$667
per person
found 1 day ago
Website advertised a pool, upon check in, there was no pool
Reviewed on Sep 1, 2026
2.5-star property
Chatham Tides
9.4/10 Exceptional! (754 reviews)
Oct 22 - Oct 27
5 night stay
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,222, price is now $905 per person
$905
per person
found 1 day ago
Oceanfront
Quiet yet convenient location
Quant
No frills, no resort fees - all a plus
Mini kitchens need a microwave
Reviewed on Sep 2, 2026
3.0-star property
Sesuit Harbor House
9.6/10 Exceptional! (204 reviews)
Oct 22 - Oct 27
5 night stay
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,166, price is now $887 per person
$887
per person
found 1 day ago
Lovely property, clean rooms and great hospitality made our stay comfortable and enjoyable.
Reviewed on Aug 30, 2026
Top rated hotels for your Southeast Massachusetts vacation package
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Free Cancellation
Reserve now, pay when you stay
13.63 mi from city center
$199 nightly
The price is $228 total per night
$228 total
Sep 20 - Sep 21
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 tours or tickets, securing valuables, and dry cleaning/laundry. Other amenities at this spa resort include an outdoor pool, a lazy river, and a children's pool.
Pool
Hot Tub
Bayside Resort Hotel
225 Route 28 West Yarmouth MA
Free Cancellation
Reserve now, pay when you stay
16.71 mi from city center
$177 nightly
The price is $202 total per night
$202 total
Sep 20 - Sep 21
Total with taxes and fees
At Bayside Resort Hotel, guests enjoy an indoor pool, a gym, and a sauna. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help secure valuables, and answer any questions about the area. Other amenities at this beach hotel include free WiFi in public areas, a hot tub, and conference space.
Pool
Hot Tub
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
$143 nightly
The price is $160 total per night
$160 total
Sep 7 - Sep 8
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.
Breakfast included
Pet friendly
Don't see what you're looking for?
See all available properties in Southeast Massachusetts
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
Explore More Ways to Travel with Travelocity
- Hostels in New England
- Beach Resorts & in New England
- Cheap Hotels in New England
- New England Hotels
- Houseboats in New England
- Cabin Rentals in Eastern Massachusetts
- Condo Rentals in Eastern Massachusetts
- Cottages in Eastern Massachusetts
- All Inclusive Resorts & in Eastern Massachusetts
- Beach Resorts & in Eastern Massachusetts
- Casino Resorts & in Eastern Massachusetts
- Kid Friendly Hotels in Eastern Massachusetts
- Gay Friendly Hotels in Eastern Massachusetts
- Hotels with Free Breakfast in Eastern Massachusetts
- Hotels with Hot Tubs in Eastern Massachusetts
- Hotels with an Indoor Pool in Eastern Massachusetts
- Hotels with Kitchenettes in Eastern Massachusetts
- Hotels with Waterslides in Eastern Massachusetts
- Eastern Massachusetts Hotels
- Motels in Eastern Massachusetts
- Vacation Homes in Eastern Massachusetts
- 4 Star Hotels in Merrimack Valley
- Extended Stay Hotels in Merrimack Valley
- Guest Houses in Merrimack Valley
- Casino Resorts & in Merrimack Valley
- Historic Hotels in Merrimack Valley
- Hotels with Balconies in Merrimack Valley
- Hotels with Bar in Merrimack Valley
- Hotels with Free Airport Shuttle in Merrimack Valley
- Hotels with an Indoor Pool in Merrimack Valley
- Hotels with Room Service in Merrimack Valley
- Pet Friendly Hotels in Merrimack Valley
- Spa Resorts & in Merrimack Valley
- Hotels with a Wedding Venue in Merrimack Valley
- Merrimack Valley Hotels
- Inns in Merrimack Valley
- Motels in Merrimack Valley
- Rv Parks in Merrimack Valley
- Hotels near Milton Pond
- Hotels near Catamount Ski Area
- Hotels near New York Harbor
