Southeast Massachusetts Holidays

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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 Town

Nantucket Town

While visiting Nantucket Town, you might make a stop by sights like Fire Hose Cart House and Nantucket Atheneum.

Find hotels in Nantucket Town

Southeast Massachusetts Holiday

Our pick of the best Southeast Massachusetts Hotel Deals

Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
The price is NZ$316 per night from 17 June to 18 June
NZ$316
17 June - 18 June
includes taxes & fees
8.6/10 Excellent! (248 reviews)
"The check in was good. Very nice young woman tending to the desk. My MAJOR complaint comes from the embarrassingly terrible breakfast: Stale bread, beige colored water being handed off as coffee, no fruit, terrible presentation. For a place that sells itself as a spa retreat, my day was sour after ..."

Reviewed on 10 June 2026

Iris Hotel Cape Cod
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
The price is NZ$377 per night from 21 June to 22 June
NZ$377
21 June - 22 June
includes taxes & fees
8.8/10 Excellent! (1,538 reviews)
"Breakfast was good, nice to have inside and outside pool lovely views across the Salt Marsh. Coffee available all day. Downside- Looking slightly tired and housekeeping did happen at all."

Reviewed on 8 June 2026

Bayside Resort Hotel
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 NZ$505 per night from 14 June to 15 June
NZ$505
14 June - 15 June
includes taxes & fees
Margaritaville Resort Cape Cod
See all 11,640 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.

Discover the most popular places to visit in Southeast Massachusetts

Gillette Stadium

Gillette Stadium

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

Gillette Stadium
Hyannis Harbor

Hyannis Harbor

4.5/5(2 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.

Hyannis Harbor
Inkwell beach in oak bluffs on martha's vineyard

Inkwell Beach

If a restful holiday is part of your travel plans, Inkwell Beach might be the perfect place to visit during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront or simply enjoy its wineries.

Inkwell Beach

What to do in Southeast Massachusetts

Moby Dick's New Bedford Smartphone Guided Walking Tour

Moby Dick's New Bedford Smartphone Guided Walking Tour

NZ$13
per adult
Moby Dick's New Bedford Smartphone Guided Walking Tour
See all activities in Southeast Massachusetts

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.