Southeast Massachusetts Holidays

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Your Southeast Massachusetts Holiday

Our Southeast Massachusetts holiday packages provide an affordable, easy and immersive way to enjoy all that this exciting destination has to offer. If it's festivals and history you're looking for, this is the place to be. With so much to see on a trip to Southeast Massachusetts, it can be tricky to know where to start. Kick off your journey in Hyannis at Cape Codder Water Park and Cape Cod Inflatable Park — two much-loved attractions here. Another city worth adding to your itinerary is Braintree. Don't miss Nantasket Beach and Wollaston Beach. Expedia has flights, hotels and everything else you need to help you organise your very own tailored Southeast Massachusetts holiday today.

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 featuring a marina, boating and a bay or harbour

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

Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree

3.5 out of 5
50 Forbes Road, Braintree, MA
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 2 Nov to 3 Nov
AU$191
per night
2 Nov - 3 Nov
9/10 Wonderful! (2,544 reviews)
"Excellent dining and shopping spots walking distance from hotel. Fantastic service!"

Reviewed on 1 Oct 2025

Hyatt Place Boston/Braintree
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$212 per night from 4 Nov to 5 Nov
AU$212
per night
4 Nov - 5 Nov
7.4/10 Good! (1,034 reviews)
"As soon as I walked in our comfy room. It reeked of mold. Besides that, all was fine!"

Reviewed on 1 Oct 2025

Best Western Adams Inn Quincy-Boston
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd, Hyannis, MA
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (370 reviews)
"Everything was perfect"

Reviewed on 27 Sept 2025

Get rates
Margaritaville Resort Cape Cod
See all 11,112 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

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
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
Plymouth Rock which includes a park as well as a small group of people

Plymouth Rock

No American historical tour is complete without a personal encounter with this symbol of national identity and origins.

Plymouth Rock

Frequently asked questions

Can I cancel my flight booking to Southeast Massachusetts due to COVID-19?
In response to these difficult times, many air carriers are offering greater flexibility. Click through to our Customer Service Portal to get important information about changing or cancelling your flight due to COVID-19.
What's the best way to find cheap flights to Southeast Massachusetts that have flexible change policies?
By using our handy "No change fee" filter, that's how. Simply enter your travel details, click the "Search" button, then select the box directly underneath the "Flexible change policies" heading (to the left of your screen). Expedia makes it a snap to find flexible and affordable fares to Southeast Massachusetts.
What are some of the general tips for travellers to Southeast Massachusetts during the COVID-19 outbreak?
If it's your first time travelling during the COVID-19 pandemic, you'll notice plenty of new rules and standards in place. Take note of these tips and make your journey to Southeast Massachusetts a smooth one:
  • Before locking in your flight, find out if any travel restrictions or bans apply — in both your destination and origin. Get up-to-date information by reviewing government websites.
  • Wear a face mask even during airport screening. A TSA employee will require you to temporarily lower your mask for ID purposes.
  • You're no longer required to hand your boarding pass (paper or electronic) directly to a TSA employee. Instead, place your pass on the scanner and then hold it up for the agent to visually inspect it.
  • You're allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on bag. You'll need to remove it for screening.
  • Empty everything from your pockets, such as your wallet, coins and keys, and put them in your carry-on rather than the bins. This will reduce handling during screening.
  • Separate any food you have for X-ray scanning. Putting it in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to Southeast Massachusetts?
Cape Air is a popular carrier servicing Southeast Massachusetts. Search for a ticket to Logan Intl. Airport (BOS) and you'll have 1785 Cape Air flights a month to select from.
How can I find cheap tickets to Southeast Massachusetts?
For the best deal to Southeast Massachusetts, book well ahead of time. Also think about using Expedia's "flexible dates" feature at the top of your search results. This will display prices for nearby days. In the last seven days, was the best price for a flight to Southeast Massachusetts.
How much is a flight to Southeast Massachusetts?
In the last seven days, round-trip flights to Southeast Massachusetts sold for as little as and reached a maximum of . For one-way journeys departing from (), the lowest amount paid during this same period was .
What are the most popular airports to fly into in Southeast Massachusetts?
Book your flight to Logan Intl. Airport (BOS) and experience everything that Southeast Massachusetts has to offer. As the region's primary entry point, about 12051 flights land here each month.
When is the cheapest time to fly to Southeast Massachusetts?
Jetting off on a Tuesday, followed by a Monday, is usually the best way to score the cheapest fare. Avoid weekends if possible, because Saturday is typically the most expensive day of the week. Spend the cash you saved enjoying yourself in Southeast Massachusetts instead!
How much is a plane ticket to Southeast Massachusetts?
Fares to Southeast Massachusetts ranged from to in the last seven days. Generally, the sooner you book the better the price.
Which airlines with flights to Southeast Massachusetts employ COVID-19 cleanliness policies?
As travel restrictions start to lift, most airlines are back in business with new measures including social distancing and increased sanitization. Here's what a few carriers are doing to help stop the spread of COVID-19:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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