Southeast Massachusetts Vacation Packages 2026 from $766

Southeast Massachusetts flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Meco Hotel - Hostel

West End

Save 100% on your flight

$766

per person

Jul 30 - Aug 2

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

A coffee shop, free WiFi in public areas, and a snack bar/deli are available at this hostel. Express check-in is also provided.

Boston Harbor Hotel

North End

$1,231

per person

Aug 5 - Aug 9

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Hotel Ivy Boston Common

Bay Village

Save 100% on your flight

$782

per person

Aug 5 - Aug 9

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

Free WiFi in public areas, luggage storage, and a safe deposit box are available at this hotel. There's locker space and multilingual staff can provide around-the-clock assistance.

Sea Crest Beach Resort

Save 100% on your flight

$2,498

per person

Jul 18 - Jul 25

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

A private beach, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the picnic area.

The Langham, Boston

Downtown Boston

$910

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.

Top Southeast Massachusetts hotels deals

Garner Hotel Brockton - Boston by IHG

405 Westgate Dr. Brockton MA

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$132 total

May 31 - Jun 1

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$251 total

May 20 - May 21

Total with taxes and fees

This smoke-free resort features a full-service spa, a water park, and 2 restaurants. There's fun for all ages with a lazy river and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the outdoor pool and perks like free self parking and free WiFi.

Pool

Hot Tub

AutoCamp Cape Cod

836 Palmer Avenue Falmouth MA

$138 nightly

$158 total

Jun 2 - Jun 3

Total with taxes and fees

This holiday park doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A coffee shop, a terrace, and a garden are also on offer.

Pet friendly

Parking included

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$167 total

May 20 - May 21

Total with taxes and fees

This hotel features 2 poolside bars, 2 bars/lounges, and an indoor pool. Enjoy the gym and free perks like buffet breakfast and free self parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Pool

Hot Tub

Summercamp

70 Lake Avenue Oak Bluffs MA

$238 nightly

$266 total

May 20 - May 21

Total with taxes and fees

This hotel features free WiFi in public areas, concierge services, and self parking. A snack bar/deli and luggage storage are also provided.

Free WiFi

Air conditioning

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

867 Iyannough Road Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$123 total

May 28 - May 29

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free continental breakfast each morning.

Pool

Breakfast included

Don't see what you're looking for?

See all available properties in Southeast Massachusetts

View all properties

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.

Popular places to visit

Gillette Stadium

4.5/5(400 reviews)

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Hyannis Harbor

4.5/5(603 reviews)

See the Cape Cod peninsula from a different perspective by riding a boat out of this picturesque harbor or wandering along its docks and jetties.

Cape Cod National Seashore

4.5/5(624 reviews)

Covering over miles of shoreline around Cape Cod, this national park offers endless things to see and do regardless of the season.

Frequently asked questions

How much are vacation packages to Southeast Massachusetts?

You can land an awesome flight and hotel bundle for an affordable $766. With a Travelocity vacation package, a getaway in Southeast Massachusetts has never looked so good! Save both time and money and get an early start with packing your suitcases.

Where can I get the best vacation package deals for Southeast Massachusetts?

For an amazing Southeast Massachusetts package deal, nothing compares to Travelocity. Take your pick from as many as 400 airlines and 1,000,000 properties around the globe to create your ideal adventure — the choice is all yours!

Why should I book my Southeast Massachusetts vacation bundle with Travelocity?

We take the hassle out of travel planning. Whether you're seeking an amazing new place to wander around or want to ensure you get the best deal around, we're here to assist. Our 24/7 support, high-quality service and Price Match Guarantee mean you can book with confidence.

Can I save money on my Southeast Massachusetts car rental if I combine it with hotels and flights?

You certainly can with our Southeast Massachusetts vacation packages. With one of these, there are loads of ways to stretch your budget further. Combine any two or more car, flight, hotel and tour bookings and see the savings pile up. With your own set of wheels, all the key sights in and around Southeast Massachusetts are within reach.

Which airport is best for Southeast Massachusetts?

Most visitors head to Southeast Massachusetts through Logan Intl. Airport (BOS) or T.F. Green Airport (PVD). Martha's Vineyard Airport (MVY) is another popular choice.

What is there to do in Southeast Massachusetts?

A diverse and inspiring destination, Southeast Massachusetts offers some incredible things to see and do. Plymouth Rock and National Monument to the Forefathers are among the most popular.