Southeast Massachusetts Holidays

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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
A harbor with several boats, including a red boat named "Kentucky" and a white boat named "Serenity."

Nantucket Town

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

A coastal town with a harbor, a large cruise ship docked, and a prominent church steeple.

Downtown Nantucket

If you're spending some time in Downtown Nantucket, Nantucket Atheneum and Whaling Museum are top sights worth seeing.

A building with a sign that reads "Whaling Museum" and a flag. There are trees, a bench, and a bicycle.

West of Town

While visiting West of Town, you might make a stop by sights like Nantucket Historical Association and Loines Observatory.

A marina with numerous sailboats and yachts anchored in calm waters.

Falmouth Heights

If you're spending some time in Falmouth Heights, Falmouth Heights Beach and Island Queen Ferry are top sights worth seeing.

A lighthouse on a grassy hill with a clear sky and the sun setting in the background.

Katama

While visiting Katama, you might make a stop by sights like South Beach and Norton Point Beach.

Top hotels in Southeast Massachusetts

Best Western Adams Inn Quincy-Boston

Best Western Adams Inn Quincy-Boston

29 Hancock St Quincy MA
4.418.607 ₫
4.935.584 ₫ total
20 Sept - 21 Sept
includes taxes & fees
Best Western Adams Inn Quincy-Boston
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
3.876.768 ₫
5.923.510 ₫ total
20 Sept - 21 Sept
includes taxes & fees
8.6/10 Excellent! (761 reviews)
"Felt like we were down south! Loved it here! Something for everyone."

Reviewed on 15 Sept 2026

Margaritaville Resort Cape Cod
Iris Hotel Cape Cod

Iris Hotel Cape Cod

291 Jones Rd Falmouth MA
3.446.272 ₫
3.944.259 ₫ total
12 Oct - 13 Oct
includes taxes & fees
Iris Hotel Cape Cod
See all 11,354 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.

Stay near popular Southeast Massachusetts attractions

A soccer stadium with a crowd of spectators, a goalpost, and players in action.
Photo by The Curious Zephyr

Gillette Stadium

9.0/10 (1,182 reviews)
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's great live music and acclaimed theatre scene.
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A beach with a lifeguard tower, a rocky breakwater, and the ocean.

Inkwell Beach

9.0/10 (154 reviews)
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.
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A sunset over a snow-covered beach with dunes and grasses.
Photo by Elizabeth Sanders

Mayflower Beach

9.2/10 (224 reviews)
Why not spend a care-free afternoon at Mayflower Beach during your travels in Dennis? While you're in the area, stroll along the waterfront.
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A neon-lit storefront with a sign for 'Lobster Pot' and 'Steaks'.
Photo by Jennywisearcade

Commercial Street

9.6/10 (523 reviews)
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.
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Xfinity Center

8.4/10 (299 reviews)
You can enjoy a show at Xfinity Center on your trip to Mansfield. Experience the area's acclaimed theatre scene or attend a sporting event.
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Patriot Place

9.4/10 (366 reviews)
You can enjoy retail therapy at Patriot Place during your visit to Foxborough. While you're in the area, find time to visit its shops.
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Frequently asked questions

How much does a Southeast Massachusetts holiday package cost?
Starting from a low , 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 1null000null000 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.