Southeast Massachusetts Vacation Packages 2026 from $433

Your Southeast Massachusetts Vacation

Our Southeast Massachusetts vacation packages provide an affordable, easy and immersive way to enjoy all that this exciting destination has to offer. If it's festivals and history you're looking for, this is the place to be. With so much to see on a trip to Southeast Massachusetts, it can be tricky to know where to start. Kick off your journey in Hyannis at Cape Codder Water Park and Cape Cod Inflatable Park — two much-loved attractions here. Another city worth adding to your itinerary is Braintree. Don't miss Nantasket Beach and Wollaston Beach. Expedia has flights, hotels and everything else you need to help you organize your very own tailored Southeast Massachusetts vacation today.

The Latest Southeast Massachusetts vacation packages

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

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$433

per person

Oct 5 - Oct 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

8.4/10 Very Good! (190 reviews)

Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Luxury Apartments by Hyatus at Boston Everett

$1,408

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9/10 Wonderful! (6 reviews)

We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week. We did not have a rental car but the parking garage was easily accessible and secure. We were able to get ubers very easily from the location. The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient. The support staff replied to all our messages in the chat option quickly and were very helpful. The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred. Would recommend this place without hesitation.

Reviewed on Jun 15, 2026

The Langham, Boston

Downtown Boston

Save 100% on your flight

$959

per person

Sep 19 - Sep 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.6/10 Exceptional! (1,002 reviews)

Elegant surroundings. The service was very good, especially the valet, who was very busy but we did not have to wait at all for our car. Very nice restaurants at the hotel property.

Reviewed on Aug 12, 2026

The Atlas Hotel

Allston

Save 100% on your flight

$1,447

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.4/10 Exceptional! (254 reviews)

The hotel was clean and well maintained. Very innovative designed. The staff was constantly hospitable - opening every door when we enter. The only downside was the room next to us was very loud on our last night which kept us up most of the night - nothing to do with the hotel. I didn’t complain and am hoping for some compensation back.

Reviewed on Aug 10, 2026

Boston Harbor Hotel

North End

Save 100% on your flight

$1,268

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (1,006 reviews)

We weren't quite sure what to expect in a hotel in the heart of Boston but were extremely pleased with the experience and the room. The room/suite was a perfect size to relax in after a busy day seeing the sights of the city, and while our view was of the city and not the harbor, it was nonetheless wonderful. The room was appointed very tastefully and invited you to rest, The hotel and room had an air of quiet luxury which we did not expect. We very much enjoyed having breakfast by the dock/water and each time, the wait staff were so friendly and helpful. There is no question we will stay there again should our plans take us to Boston. Thanks helping to make our anniversary trip so great!

Reviewed on Aug 12, 2026

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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

Discover the charm of Nantucket, a historic New England seaport town, with its museums like the Nantucket Whaling Museum and picturesque landscapes. Enjoy local shops, restaurants, and explore key localities such as Surfside and Siasconset.

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 lighthouse with a house nearby, under a starry night sky with visible Milky Way.

Bass River

Estuary village Bass River offers kiteboarding at West Dennis Beach, windsurfing at Kalmus Beach, and attractions like Marsh Island and Windmill Beach. Enjoy a round at Bass River Golf Course too!

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.

New Seabury

Travelers like the museums in New Seabury, and South Cape Beach State Park is a top attraction you might want to visit.

Stay near popular Southeast Massachusetts attractions

A soccer stadium with a crowd of spectators, a goalpost, and players in action.

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 theater scene.

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A coastal landscape with sand dunes, green vegetation, and the ocean in the background.

Cape Cod National Seashore

9.6/10 (1,134 reviews)

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

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A neon-lit storefront with a sign for 'Lobster Pot' and 'Steaks'.

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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A sunset over a snow-covered beach with dunes and grasses.

Mayflower Beach

9.2/10 (224 reviews)

Why not spend a carefree afternoon at Mayflower Beach during your travels in Dennis? While you're in the area, stroll along the waterfront.

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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 vacation is part of your travel plans, Inkwell Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront, or simply enjoy its wineries.

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Xfinity Center

8.4/10 (299 reviews)

You can make plans for a show at Xfinity Center on your trip to Mansfield. Experience the area's acclaimed theater scene or attend a sporting event.

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What to do in Southeast Massachusetts

Moby Dick's New Bedford Smartphone Guided Walking Tour

per adult

See all activities in Southeast Massachusetts

Southeast Massachusetts Hotel Deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

$230 nightly

$263 total

Sep 7 - Sep 8

Total with taxes and fees

Iris Hotel Cape Cod

291 Jones Rd Falmouth MA

Fully refundableReserve now, pay when you stay

$136 nightly

$156 total

Sep 7 - Sep 8

Total with taxes and fees

8.4/10 Very Good! (332 reviews)

"L"

Reviewed on Aug 12, 2026

Sonesta Select Boston Foxborough Mansfield

35 Foxborough Boulevard Foxborough MA

Fully refundableReserve now, pay when you stay

$99 nightly

$111 total

Aug 24 - Aug 25

Total with taxes and fees

8.6/10 Excellent! (1,000 reviews)

"It was easy to find and quiet. We enjoyed the breakfast and our room had everything we needed."

Reviewed on Aug 12, 2026

See all 11,474 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.

Find the Best Southeast Massachusetts Vacation Packages

Things to do near Southeast Massachusetts

Southeast Massachusetts offers a delightful blend of outdoor adventures and urban experiences perfect for family vacations. Enjoy summer festivals, community events, and a variety of outdoor activities in picturesque recreation areas. Indulge in local flavors during restaurant week, and explore shopping centers and golf courses for a well-rounded getaway. Whether you're relaxing at a spa or immersing yourself in the vibrant local culture, there's something for everyone to enjoy.

Shopping

Mashpee Commons, located 10 miles away, offers a vibrant shopping experience with entertainment and family-friendly activities. For unique gifts, visit Wings & Things, just 9 miles from Southeast Massachusetts. Don’t miss the Raynham Flea Market, 25 miles away, where you can find a variety of treasures in a lively atmosphere.

Recreation

At Cape Cod Country Club, enjoy upscale amenities and beautiful surroundings for a relaxing day. Doran Park offers invigorating sports activities, perfect for those looking to stay active. Lyman Reserve is a serene spot for wellness and relaxation, surrounded by nature’s beauty, ideal for unwinding and rejuvenating.

Adventure

At Water Wizz, located 5 miles from Southeast Massachusetts, you can dive into thrilling water slides and relax in the wave pool, offering a fun-filled day for the entire family. The Shining Sea Bikeway, 8 miles away, invites you to explore scenic coastal views on your bike, perfect for outdoor enthusiasts.

Nightlife

Southeast Massachusetts offers vibrant nightlife options. Enjoy craft cocktails at The Whaling City Tavern in New Bedford, or dance the night away at The Vault in Fall River. For a laid-back vibe, visit The Bar at the Cove in Wareham, perfect for mingling with locals.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Southeast Massachusetts

Southeast Massachusetts offers a perfect blend of outdoor adventures and city experiences, making it ideal for family vacations. Visitors can explore beautiful beaches, fascinating history museums, and serene nature preserves. The region caters to those seeking cultural enrichment and outdoor fun. Don't forget to check for local public holidays and special events during your visit, especially around Christmas, to enhance your experience in this vibrant part of the Commonwealth of Massachusetts.

Old Silver Beach: Located only 4 miles away, Old Silver Beach offers a perfect seaside escape with its soft sands and gentle waves. Enjoy sunbathing, swimming, and beachcombing, all while basking in the warm beach vibes that make it a favorite for families and sun-seekers alike.
Massachusetts Maritime Academy: About 5 miles from Southeast Massachusetts, this modern college campus boasts impressive facilities and a unique maritime focus. Visitors can explore the vibrant atmosphere and gain insights into maritime education, all while enjoying the dynamic city vibes surrounding the academy.
Wings Neck Lighthouse: Just 0.3 miles away, this historic lighthouse is a charming landmark steeped in maritime culture. Its stunning views and rich history make it a delightful spot for photography and learning about the region's seafaring past.

Best time to go to Southeast Massachusetts

The best time to visit Southeast Massachusetts is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	34.2°F (1.2000000000000002°C)	Light Rain	Mostly Sunny	Low	Slightly Low
February	34.5°F (1.4°C)	Light Rain	Mostly Cloudy	Low	Average
March	38.3°F (3.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	48.2°F (9.0°C)	Light Rain	Mostly Sunny	Average	Average
May	56.3°F (13.5°C)	Light Rain	Mostly Sunny	Average	Average
June	63.3°F (17.400000000000002°C)	Light Rain	Mostly Sunny	High	Slightly High
July	71.2°F (21.8°C)	Light Rain	Mostly Sunny	High	Slightly High
August	70.7°F (21.5°C)	Light Rain	Mostly Sunny	High	Slightly High
September	65.5°F (18.6°C)	Light Rain	Mostly Sunny	Average	Average
October	56.5°F (13.6°C)	Light Rain	Mostly Sunny	Average	Average
November	45.9°F (7.7°C)	Light Rain	Mostly Sunny	Average	Average
December	38.3°F (3.5°C)	Light Rain	Mostly Sunny	Low	Slightly Low

Tips to save on your trip to Southeast Massachusetts

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Southeast Massachusetts.
Consider traveling during the off-peak season (typically March and December to January) for more affordable package holidays to Southeast Massachusetts.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.