Southeast Massachusetts Trip

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Top Southeast Massachusetts Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was ₹109,717, price is now ₹73,867 per person
₹73,867
per person
30 Mar - 4 Apr
found 20 hours ago
Return flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Great gym and staff. Kudos to Nicky at the front desk.

Reviewed on 22 Feb 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ₹238,390, price is now ₹125,647 per person
₹125,647
per person
30 Mar - 4 Apr
found 20 hours ago
Return flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on 25 Jan 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was ₹120,790, price is now ₹77,570 per person
₹77,570
per person
30 Mar - 4 Apr
found 20 hours ago
Return flight included
Chicago (CHI) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
I had a pleasant stay there. The receptionists are so nice and helpful. I came early before the checking time but they let me in. Extending reservation was also easy and they're helpful. They let me come back in after my buses were cancelled, and that's a very great service. They provided good amenities too. So far, it's been a comfortable stay in the hotel; and the location is quite near with the north station and stores if you need to buy meals just in case.

Reviewed on 24 Feb 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was ₹230,063, price is now ₹149,497 per person
₹149,497
per person
30 Mar - 4 Apr
found 20 hours ago
Return flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
The most perfect hotel and service I’ve ever experienced in my lifetime!

Reviewed on 24 Feb 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was ₹164,975, price is now ₹114,018 per person
₹114,018
per person
30 Mar - 4 Apr
found 20 hours ago
Return flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Friendly staff, clean room

Reviewed on 20 Feb 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
From the dock.

Nantucket Town

While visiting Nantucket Town, you might make a stop by sights like Vestal St Observatory and Nantucket Atheneum.

Find hotels in Nantucket Town

Top hotels in Southeast Massachusetts

Holiday Inn Express Brockton - Boston by IHG

Holiday Inn Express Brockton - Boston by IHG

2.5 out of 5
405 Westgate Dr. Brockton MA
Fully refundable
The price is ₹8,822 per night from 8 Mar to 9 Mar
₹8,822
₹9,854 total
8 Mar - 9 Mar
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
Yes

Reviewed on 25 Feb 2026

Holiday Inn Express Brockton - Boston by IHG
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
The price is ₹12,024 per night from 8 Mar to 9 Mar
₹12,024
₹18,963 total
8 Mar - 9 Mar
includes taxes & fees
8.6/10 Excellent! (465 reviews)
The updates they made are beautiful. You really feel like you’re in the Caribbean if you don’t step outside. All the staff I encountered were super helpful and courteous. The water park was closed for unforeseen maintenance for a day and a half which happened to be out last days so that was disappointing ...

Reviewed on 25 Feb 2026

Margaritaville Resort Cape Cod
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
The price is ₹9,735 per night from 9 Mar to 10 Mar
₹9,735
₹12,959 total
9 Mar - 10 Mar
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Good stay over. Takes a bit to get deposit back.

Reviewed on 20 Feb 2026

Falmouth Inn
See all 11,143 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

Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

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

Gillette Stadium
Cape Cod National Seashore showing tranquil scenes and general coastal views

Cape Cod National Seashore

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
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

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.