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.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Located in a new neighborhood with lots of dining options and easy access to public transportation.

Reviewed on 28 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,964 reviews)
Great location. Easy access to the City.

Reviewed on 29 Jul 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
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Reviewed on 28 Jul 2025

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 showing a bay or harbour, a marina and boating

Nantucket Town

While visiting Nantucket Town, you might make a stop by sights like Theatre Workshop of Nantucket and Nantucket Atheneum.

Find hotels in Nantucket Town

Top hotels in Southeast Massachusetts

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 €192 per night from 5 Aug to 6 Aug
€192
5 Aug - 6 Aug
includes taxes & fees
8/10 Very Good! (52 reviews)
Did the trick
"Clean room, building and rooms are a bit dated. Would return, fairly priced."

Reviewed on 13 Jul 2025

Iris Hotel Cape Cod
Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane, Nantucket, MA
8.8/10 Excellent! (501 reviews)
"Beautiful would definitely stay again"

Reviewed on 26 Jul 2025

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Nantucket Inn
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,432 reviews)
"Breakfast was excellent. Pools were great. Bayfront was beautiful. Worth the extra few dollars in comparison to the many others in the area."

Reviewed on 27 Jul 2025

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Bayside Resort Hotel
See all 11,249 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 featuring general coastal views and tranquil scenes

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
Nauset Beach which includes a 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 showing a garden 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

How much does a Southeast Massachusetts holiday package cost?
Starting from a low €546, 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 1,000,000 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.