Southeast Massachusetts Vacations 2025 from CA $586

Southeast Massachusetts flight + hotel packages

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

Copley House

Back Bay

Save 100% on your flight

per person

Mar. 12 - Mar. 16

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

Stay at this 3-star guesthouse in Boston. Enjoy free WiFi, parking (surcharge), and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Boston Common are located nearby.

Fairmont Copley Plaza, Boston

Back Bay

Save 100% on your flight

per person

Mar. 12 - Mar. 16

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

Stay at this 4.5-star luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Boston Common and Fenway Park are located nearby.

YOTEL Boston

Seaport District

Save 100% on your flight

per person

Mar. 12 - Mar. 16

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions Boston Common and TD Garden are located nearby.

The Newbury Boston

Back Bay

Save 100% on your flight

per person

Mar. 26 - Apr. 2

found 18 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Boston (BOS)

Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and TD Garden are located nearby.

The Revolution Hotel

South End

Save 100% on your flight

per person

Mar. 12 - Mar. 16

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and Fenway Park are located nearby.

Top Southeast Massachusetts hotels deals

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

867 Iyannough Road, Hyannis, MA

Free cancellation

Reserve now, pay when you stay

CA $152

CA $174 total

includes taxes & fees

6 Feb - 7 Feb

Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Cape Codder Water Park and Summer House Natural Soaps are located nearby.

Margaritaville Resort Cape Cod

1225 Iyannough Rd, Hyannis, MA

Free cancellation

Reserve now, pay when you stay

CA $185

CA $260 total

includes taxes & fees

2 Feb - 3 Feb

Book a stay at this family-friendly resort in Hyannis. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the clean rooms in our reviews. Popular attractions Cape Codder Water Park and Barnstable Performing Arts Center are located nearby.

Bayside Resort Hotel

225 Route 28, West Yarmouth, MA

Free cancellation

Reserve now, pay when you stay

CA $153

CA $192 total

includes taxes & fees

24 Jan - 25 Jan

Stay at this 3-star beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Putter's Paradise Miniature Golf and Bay View Street Beach are located nearby.

John Carver Inn & Spa

25 Summer Street, Plymouth, MA

Free cancellation

Reserve now, pay when you stay

CA $154

CA $187 total

includes taxes & fees

23 Jan - 24 Jan

Stay at this 3-star spa hotel in Plymouth. Enjoy free parking, a full-service spa, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Richard Sparrow House and John Jenney Museum are located nearby.

Chatham Bars Inn

297 Shore Rd, Chatham, MA

CA $475

CA $571 total

includes taxes & fees

23 Jan - 24 Jan

Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chatham Seaside Links and Chatham Fish Pier are located nearby.

Pilgrim House

336 Commercial St, Provincetown, MA

Get rates

Stay at this 3.5-star hotel in Provincetown. Enjoy free WiFi, 3 bars/lounges, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Provincetown Public Library and MacMillian Wharf are located nearby.

Don't see what you're looking for?

See all available properties in Southeast Massachusetts

View all properties

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

4.5/5(27 reviews)

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

Cape Cod National Seashore

5/5(19 reviews)

Explore the lovely green spaces of Cape Cod National Seashore and enjoy the hiking trails in Eastham. Wander the beautiful beaches and seaside in the area.

Hyannis Harbor

4.5/5(33 reviews)

Explore the waterfront in Hyannis with a trip to Hyannis Harbor. Stroll along the seaside in this family-friendly area, or check out its seafood restaurants.

Frequently asked questions

How much are vacation packages to Southeast Massachusetts?

You can land an awesome flight and hotel bundle for an affordable CA $586. With a Travelocity vacation package, a getaway in Southeast Massachusetts has never looked so good! Save both time and money and get an early start with packing your suitcases.

Where can I get the best vacation package deals for Southeast Massachusetts?

For an amazing Southeast Massachusetts package deal, nothing compares to Travelocity. Take your pick from as many as 400 airlines and 1,000,000 properties around the globe to create your ideal adventure — the choice is all yours!

Why should I book my Southeast Massachusetts vacation bundle with Travelocity?

We take the hassle out of travel planning. Whether you’re seeking an amazing new place to wander around or want to ensure you get the best deal around, we’re here to assist. Our 24/7 support, high-quality service and Price Match Guarantee mean you can book with confidence.

Can I save money on my Southeast Massachusetts car rental if I combine it with hotels and flights?

You certainly can with our Southeast Massachusetts vacation packages. With one of these, there are loads of ways to stretch your budget further. Combine any two or more car, flight, hotel and tour bookings and see the savings pile up. With your own set of wheels, all the key sights in and around Southeast Massachusetts are within reach.

Which airport is best for Southeast Massachusetts?

Most visitors head to Southeast Massachusetts through Logan Intl. Airport (BOS) or T.F. Green Airport (PVD). Martha’s Vineyard Airport (MVY) is another popular choice.

What is there to do in Southeast Massachusetts?

A diverse and inspiring destination, Southeast Massachusetts offers some incredible things to see and do. Plymouth Rock and National Monument to the Forefathers are among the most popular.