Southeast Massachusetts Beach Vacations

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Top Beach vacation packages in Southeast Massachusetts

Price found within the past 48 hours. Click for updated prices.
The Beachside

The Beachside

Nantucket Town
$834
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Rock Springs (RKS) to Boston (BOS)
9.4/10 Exceptional! (352 reviews)
Really nice hotel, away from the craziness of the downtown area. My only complaint is that the walls are paper thin and you can hear every single movement from above. We were given a room away from the main building where there is a second level, even though I know some of the rooms closer were empty and did not have a floor above. You can hear walking, rolling of suitcases and housekeeping carts so bad. Other than that, it was a nice property.

Reviewed on Sep 28, 2026

The Mansion at Ocean Edge

The Mansion at Ocean Edge

Save 100% on your flight
$1,554
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Boston (BOS)
8.2/10 Very Good! (1,002 reviews)
The room was dirty, the tub has two holes, light switches broken. Wallpaper coming off the walls, bed had stains and the indoor pool had bugs and mold everywhere. The shower walls had black mold. The staff was not helpful at all. Carpet was not vacuumed.

Reviewed on Sep 25, 2026

Harbor View Hotel

Harbor View Hotel

$1,845
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Louisville (SDF) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,000 reviews)
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5* Beach vacations in Southeast Massachusetts

Price found within the past 48 hours. Click for updated prices.
Harbor View Hotel

Harbor View Hotel

$1,845
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Louisville (SDF) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,000 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Southeast Massachusetts
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3 Night Beach vacations in Southeast Massachusetts

Price found within the past 48 hours. Click for updated prices.
The Beachside

The Beachside

Nantucket Town
$834
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Rock Springs (RKS) to Boston (BOS)
9.4/10 Exceptional! (352 reviews)
Really nice hotel, away from the craziness of the downtown area. My only complaint is that the walls are paper thin and you can hear every single movement from above. We were given a room away from the main building where there is a second level, even though I know some of the rooms closer were empty and did not have a floor above. You can hear walking, rolling of suitcases and housekeeping carts so bad. Other than that, it was a nice property.

Reviewed on Sep 28, 2026

Harbor View Hotel

Harbor View Hotel

$1,398
per person
Nov 5 - Nov 8
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,000 reviews)
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4 Night Beach vacations in Southeast Massachusetts

Price found within the past 48 hours. Click for updated prices.
Chatham Tides

Chatham Tides

$703
per person
Nov 3 - Nov 7
found 17 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
9.4/10 Exceptional! (776 reviews)
We stayed one week at Chatham Tides and it was the PERFECT beach front location to enjoy one last summer hurrah! The location could not be any more convenient and the room amenities make it so convenient too! It was lovely having the coffee maker, fridge, and stovetop for occasional meals - but we were also so close to amazing restaurants too! The housekeeping facilities were wonderful! Additionally, there were kayaks, an outdoor shower, beach chairs, and a grill available for use! Parking was easy too! And the staff was the absolute nicest and kindest who helped us with any questions we had! We had the best week - highly highly recommend this gorgeous hotel. 12/10 stars!

Reviewed on Sep 26, 2026

Harbor Hotel Provincetown

Harbor Hotel Provincetown

Save 100% on your flight
$13,906
per person
Dec 21 - Dec 25
found 16 hours ago
Roundtrip flight included
Nashville (BNA) to Provincetown (PVC)
8.4/10 Very Good! (1,013 reviews)
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

$718
per person
Nov 3 - Nov 7
found 17 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
9.4/10 Exceptional! (226 reviews)
Our room was lovely with a beautiful ocean view! We could have stayed forever. It was quiet enough that the waves could be heard through the open window. The inn has a large veranda for breakfast overlooking the private beach. We thoroughly enjoyed our stay and hope to be back soon!

Reviewed on Sep 28, 2026

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Find your perfect Southeast Massachusetts beach vacation

How do I book the best Southeast Massachusetts beach vacation packages?

Life’s a beach when you dive into our brilliant Southeast Massachusetts beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Southeast Massachusetts?

A rental steps from the shore creates an amazingly affordable Southeast Massachusetts beach vacation. Seaside sojourns during low season start from $703. Prices and availability are subject to change. Additional terms may apply.

When should I book a Southeast Massachusetts beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Southeast Massachusetts?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Southeast Massachusetts beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Southeast Massachusetts vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Southeast Massachusetts beach vacation deals?

Sort your search results by deals to delight in amazing Southeast Massachusetts beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Southeast Massachusetts beach trip with free cancellation and/or flexible dates?

Just like the Southeast Massachusetts tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Southeast Massachusetts beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Southeast Massachusetts. (OK, maybe not that last part.)

Top Beach Southeast Massachusetts Hotels

Sea Crest Beach Resort

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA
  • 2 hours drive from Gillette Stadium
At this hotel, get ready to enjoy the sunsets on the beach in North Falmouth, as you'll be near Cape Cod Beaches. 2 restaurants, a private beach, and a beach ...
Sea Crest Beach Resort
Lighthouse Inn

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA
  • 2 hours drive from Gillette Stadium
Make the most of this fantastic location, as you'll be a short walk from Cape Cod Beaches with a holiday at this hotel. Amenities at Lighthouse Inn include a ...
8.8/10 Excellent! (325 reviews)

Travelers like: on the beach, sun loungers, beach umbrellas, beach towels

Travelers say...
"Property was absolutely breathtaking. The restaurant/bar was steps from the beach and had a beautiful interior. The accommodations were very quaint. It was like stepping back in time. They were clean and comfortable and also allowed for a beautiful view. We were there in off season so it was not ..."

Reviewed on Sep 27, 2026

Lighthouse Inn
Chatham Bars Inn

Chatham Bars Inn

297 Shore Rd Chatham MA
  • 2 hours drive from Gillette Stadium
Settle in and relax at this luxury boutique resort and get ready to stroll along the shore in Chatham, as you'll be a short walk from Cape Cod Beaches. 3 outdoor ...
Chatham Bars Inn
See all 11,302 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.

Things to do

Moby Dick's New Bedford Smartphone Guided Walking Tour

Moby Dick's New Bedford Smartphone Guided Walking Tour

$8
per adult
Moby Dick's New Bedford Smartphone Guided Walking Tour
See all activities in Southeast Massachusetts

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.