Southeast Massachusetts Holidays

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Top Flight + Hotel Deals in Southeast Massachusetts

Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was €1,840, price is now €1,359 per person
€1,359
per person
16 Jul - 20 Jul
found 1 day ago
Return flight included
Lisbon (LIS) to Boston (BOS)
8.4/10 Very Good! (1,439 reviews)
Safe, friendly staff, garage discount, great location. Easy check in and check out.

Reviewed on 18 May 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €2,751, price is now €1,725 per person
€1,725
per person
16 Jul - 20 Jul
found 1 day ago
Return flight included
Lisbon (LIS) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
This was 10/10 with everything top tier

Reviewed on 20 May 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was €2,201, price is now €1,650 per person
€1,650
per person
16 Jul - 20 Jul
found 1 day ago
Return flight included
Lisbon (LIS) to Boston (BOS)
9/10 Wonderful! (1,243 reviews)
Gorgeous hotel in a fabulous location. Highly recommend!

Reviewed on 19 May 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was €1,794, price is now €1,443 per person
€1,443
per person
16 Jul - 20 Jul
found 1 day ago
Return flight included
Lisbon (LIS) to Boston (BOS)
8.8/10 Excellent! (1,475 reviews)
Our stay here was outstanding. The staff was awesome and amazing their attentive to our needs was met with enthusiasm. Danielle, Matthew, Mauricio and the kitchen staff!!!

Reviewed on 19 May 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was €2,227, price is now €1,804 per person
€1,804
per person
16 Jul - 20 Jul
found 1 day ago
Return flight included
Lisbon (LIS) to Boston (BOS)
9.4/10 Exceptional! (1,006 reviews)
Excellent location and great staff

Reviewed on 3 May 2026

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 Nantucket Atheneum and Nantucket Historical Association.

Find hotels in Nantucket Town

Top hotels in Southeast Massachusetts

Garner Hotel Brockton - Boston by IHG

Garner Hotel Brockton - Boston by IHG

2.5 out of 5
405 Westgate Dr. Brockton MA
Fully refundableReserve now, pay when you stay
The price is €106 per night from 24 May to 25 May
€106
24 May - 25 May
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"I never even got into a room, never got a refund from either the hotel.com app or the property! Ridiculous"

Reviewed on 19 May 2026

Garner Hotel Brockton - Boston by IHG
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 €216 per night from 31 May to 1 Jun
€216
31 May - 1 Jun
includes taxes & fees
8.8/10 Excellent! (578 reviews)
"Gorgeous hotel, very clean and welcoming. We had a wonderful stay, staff was very kind."

Reviewed on 13 May 2026

Margaritaville Resort Cape Cod
AutoCamp Cape Cod

AutoCamp Cape Cod

4 out of 5
836 Palmer Avenue Falmouth MA
The price is €169 per night from 27 May to 28 May
€169
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (326 reviews)
"Staff were friendly and helpful. Room and heating could be better. But overall a good and convenient location."

Reviewed on 12 May 2026

AutoCamp Cape Cod
See all 11,557 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.

Popular places to visit

Cape Cod National Seashore

Cape Cod National Seashore

4.5/5(27 reviews)

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

Cape Cod National Seashore
Old Silver Beach

Old Silver Beach

4.5/5(7 reviews)

Go for a swim in the surprisingly warm water or enjoy the views across Buzzard Bay at Falmouth’s family-favorite beach.

Old Silver Beach
Plymouth Rock

Plymouth Rock

4/5(17 reviews)

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.