Southeast Massachusetts Holidays from AU$1,660

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Your Southeast Massachusetts Holiday

Our Southeast Massachusetts holiday packages provide an easy, affordable and immersive way to experience all that this inspiring destination has to offer. If it's festivals and history you're looking for, Brockton is a great starting point. Why not organise your trip to Southeast Massachusetts around some of its most well-known cities? Hyannis, West Yarmouth and Main Street Hyannis are terrific places to start. When you're ready to stop dreaming and start travelling, Expedia will help turn your Southeast Massachusetts holiday into reality.

The Latest Southeast Massachusetts Holiday Deals

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

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
per person
16 May - 23 May
found 10 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
8.8/10 Excellent! (1,924 reviews)
Everything well, Room Space not well!

Reviewed on 13 Mar. 2025

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
16 May - 23 May
found 10 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
7.4/10 Good! (512 reviews)
Very nice and loved the staff

Reviewed on 28 Feb. 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
16 May - 23 May
found 10 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (2,782 reviews)
Great place. Top notch

Reviewed on 13 Mar. 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Save 100% on your flight
per person
16 May - 23 May
found 10 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
8/10 Very Good! (532 reviews)
On the outskirts of Chinatown. Not alot of dining options close by other than Asian cuisine. A bit on the sketchy side, but felt safe walking during the day. Pics of the common areas are nicer than the actual. Room was good though, clean and had what we needed. Comfy bed. Shower could use an update - flow is very low.

Reviewed on 23 Feb. 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
16 May - 23 May
found 10 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
8.8/10 Excellent! (1,010 reviews)
Staff and level of service was outstanding.

Reviewed on 2 Mar. 2025

Our guide on where to stay in Southeast Massachusetts

Find the best Southeast Massachusetts areas and neighborhoods for the activities you enjoy most. Learn more about Southeast Massachusetts
Nantucket showing boating, a bay or harbour and a marina

Nantucket Town

While visiting Nantucket Town, you might make a stop by sights like Nantucket Atheneum and Nantucket Historical Association.

Find hotels in Nantucket Town

Southeast Massachusetts Holiday

Southeast Massachusetts Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Top Sights
Cape Cod National Seashore, Cape Cod Beaches and Nauset Beach

Our pick of the best Southeast Massachusetts Hotel Deals

Margaritaville Resort Cape Cod
Margaritaville Resort Cape Cod
4 out of 5
1225 Iyannough Rd, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is AU$342 per night from 16 Mar to 17 Mar
AU$342
includes taxes & fees
16 Mar - 17 Mar
8.2/10 Very Good! (102 reviews)
Fun little getaway
"Came here just for a small overnight for my Daughter. She loves an indoor water park. Check in was quick, easy and informative. Greeted nicely. Room was very clean and well decorated. Felt like I was not on the Cape. Water park is small but fun for kids. Lifeguards were all friendly and attentive. ..."

Reviewed on 10 Mar. 2025

Margaritaville Resort Cape Cod
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
2.5 out of 5
867 Iyannough Road, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 30 Mar to 31 Mar
AU$191
includes taxes & fees
30 Mar - 31 Mar
8.8/10 Excellent! (546 reviews)
Entirely perfectly located hotel
"Great location because the mall was nearby and Whole Foods IHOP across the road."

Reviewed on 8 Mar. 2025

Fairfield Inn & Suites by Marriott Cape Cod Hyannis
Best Western Adams Inn Quincy-Boston
Best Western Adams Inn Quincy-Boston
2.5 out of 5
29 Hancock St, Quincy, MA
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 24 Mar to 25 Mar
AU$203
includes taxes & fees
24 Mar - 25 Mar
7.2/10 Good! (983 reviews)
"Worn out property and not so happy staff."

Reviewed on 2 Feb. 2025

Best Western Adams Inn Quincy-Boston
See all 10,710 properties in Southeast Massachusetts
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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Southeast Massachusetts holiday package cost?
Starting from a low AU$1,660, a package is your gateway to inexpensive travel. Custom build your Southeast Massachusetts adventure by selecting from our comprehensive range of airfares, hotels and rental cars.
How do I get a cheap travel package to Southeast Massachusetts?
One word: bundle. Flights, rental cars and hotels — combine whatever you need into a Southeast Massachusetts holiday package and save. Score even better deals when you include extras such as activities or tours to your booking. But that’s not the only impressive part. You have the freedom to customize your trip your way. We offer over 550 airlines and 1 000 000 hotel options in all corners of the globe, so that everyone has a chance to travel and fulfil those holiday fantasies.
Where should I stay in Southeast Massachusetts?
Plymouth is a fantastic place to include in your itinerary. It’s where you’ll find well-known sights including Plymouth Rock and Mayflower II. Provincetown also draws in many wanderers eager to explore some of the best attractions in Southeast Massachusetts. Two of the best are Pilgrim Monument and Herring Cove Beach.
What are the top hotels in Southeast Massachusetts?
When it comes to hotels in Provincetown, Hampton Inn Boston - Logan Airport and Boston Park Plaza are two terrific options. If you’re also visiting Brewster, Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel will make you feel right at home.
How far in advance should I book my Southeast Massachusetts holiday?
While not all air carriers release tickets early, customers are usually able to start comparing international fares on Expedia up to a year in advance. This is the time you’ll score some fantastic deals. If you’re booking late, you could still be in luck. Discounted prices occasionally emerge a few weeks prior to departure.
What does an Expedia Southeast Massachusetts travel package include?
Flights, rental cars and hotels — you’ll find them all here. With Expedia, you can shape your Southeast Massachusetts package the way you want. All you have to do is decide exactly what you need. Once you’ve made your booking, you can add extras like activities and tours. The more you bundle, the greater your savings!
What should I know before booking a Southeast Massachusetts travel package?
Bundling your bookings into a Southeast Massachusetts holiday package is the most convenient way to organise your trip. Not only that, you’ll save just for combining your hotels, flights and car rentals. Once you’ve booked, why not add on an activity or a tour?
Can I choose my airline with a Southeast Massachusetts Expedia holiday package?
Yes — that’s one of the best things about an Expedia package. You’re the boss! We have more than 550 partner airlines all over the world, so you have options galore when arranging your Southeast Massachusetts adventure.
If I'm not able to travel, can I cancel my Southeast Massachusetts holiday package?
You can. We understand that life doesn’t always go to plan, so we’re happy to help if you have to make changes to your Southeast Massachusetts holiday package. You may be able to cancel or change your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Southeast Massachusetts

Commercial Street

Commercial Street

Enjoy a stop at Commercial Street, an entertaining place to visit in Provincetown. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Commercial Street
Plymouth Harbor which includes a marina and a coastal town

Plymouth Harbor

4.5/5(4 reviews)

Visit the place where the Mayflower dropped anchor and the Pilgrims first touched the New World, a focal point of any visit to Plymouth.

Plymouth Harbor
Nauset Beach showing a sandy beach as well as a couple

Nauset Beach

Vast expanses of white sand, light blue water and gentle waves mingle with the sounds of seabirds and seals at this secret gem in Cape Cod.

Nauset Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.