Southeast Massachusetts Vacation Packages for 2026

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Southeast Massachusetts Flight + Hotel packages

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

Arcadian Hotel

Coolidge Corner
$777
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

North End
$1,190
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Good Hotels Boston

Good Hotels Boston

South End
Save 100% on your flight
$1,362
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, laundry facilities, and bathrobes. Popular attractions Copley Square and Fenway Park are located nearby.
Very nice people and had excellent help!

Reviewed on Aug 7, 2026

Encore Boston Harbor

Encore Boston Harbor

Save 100% on your flight
$1,174
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Very nice stay.

Reviewed on Aug 18, 2026

Eurostars The Boxer

Eurostars The Boxer

West End
Save 100% on your flight
$1,044
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
The house keeping staff was the best in all my last 25 years of traveling on Hotels and my cruises on various cruise lines.

Reviewed on Aug 18, 2026

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

North End
Save 100% on your flight
$1,770
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Harbor and Faneuil Hall Marketplace are located nearby.
Almost everything was absolutely perfect except for two little things. I stayed in building 4, and the two sets of glass doors were quite heavy. Maybe I missed it, but I didn't see a button to push to open the doors automatically, so getting my luggage through the doors was difficult. My only other suggestion is to add a small fridge to the room. Other than that, what an absolutely stunning and peaceful hotel and there is so much stuff to do and see within walking distance. Definitely hop on bus 66 to the water taxi from Logan Airport. It's not expensive at all, you can book the water taxi online, and the boat drops you off right at the entrance to the hotel. Captain Jamie was a very nice guy!! bostonwatertaxi.com

Reviewed on Aug 17, 2026

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Southeast Massachusetts Vacation Packages

Trying to plan a way to package your Southeast Massachusetts flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Southeast Massachusetts vacation packages can help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Southeast Massachusetts incredible. Our Travel Center is a one-stop shop where you can put together the best Southeast Massachusetts vacation package for you and your family. We have a fabulous choice of flights and lodgings, as well as local endeavors to pick from.

Southeast Massachusetts Hotels

Our listings include accommodations that are close to all the Southeast Massachusetts points of interest, and others that are just outside the city center for a peaceful retreat.

We have great deals on everything from luxury hotels that satisfy all the vacation must-haves to affordable hotels perfect for those on looking to save. You can search all the possibilities and choose the lodging that is ideal for you. With AARP Travel Center's Southeast Massachusetts hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.

Things to do in Southeast Massachusetts

The fact that you are traveling to Southeast Massachusetts means your holiday is already off to a great start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.

If you need more suggestions, then make sure to click on AARP's "Things to Do" tab.

Save with a Southeast Massachusetts Vacation Package

With so much to see and do in Southeast Massachusetts, you'll be wanting to focus on your itinerary, not devoting time to finding the cheapest hotel. AARP Travel Center allows you to quickly book everything you wish for, and save money while doing it. You can plan your entire holiday, including things to do in Southeast Massachusetts from only one site. The hardest packing you'll have to do is for your suitcase. Book now and save!

Top Hotel Deals

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA
21.95 km from city center
Book a stay at this spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions ...
Iris Hotel Cape Cod

Iris Hotel Cape Cod

291 Jones Rd Falmouth MA
20.8 km from city center
Book a stay at this business-friendly hotel in Falmouth. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Falmouth Heights Beach ...
Sonesta Select Boston Foxborough Mansfield

Sonesta Select Boston Foxborough Mansfield

35 Foxborough Boulevard Foxborough MA
65.11 km from city center
Book a stay at this business-friendly hotel in Foxborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Nantucket Inn

Nantucket Inn

1 Miller Lane Nantucket MA
67.7 km from city center
Book a stay at this business-friendly resort in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA
26.39 km from city center
Book a stay at this beach hotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the restaurant in our reviews. ...
Bayside Resort Hotel

Bayside Resort Hotel

225 Route 28 West Yarmouth MA
26.91 km from city center
Book a stay at this beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

1470 Iyannough Road Hyannis MA
21.32 km from city center
Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Falmouth Inn

Falmouth Inn

824 Main Street Falmouth MA
21.27 km from city center
Book a stay at this business-friendly hotel in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Lighthouse Inn

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA
33.84 km from city center
Book a stay at this beach hotel in West Dennis. Enjoy free WiFi, free parking, and private plunge pools. Our guests praise the helpful staff in our reviews. ...
Hyannis Harbor Hotel

Hyannis Harbor Hotel

213 Ocean St Hyannis MA
25.41 km from city center
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff in our ...
Pilgrim Sands on Long Beach

Pilgrim Sands on Long Beach

150 Warren Ave Plymouth MA
22.56 km from city center
Book a stay at this beach hotel in Plymouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA
36.18 km from city center
Book a stay at this family-friendly motel in Dennis Port. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Harbor Hotel Provincetown

Harbor Hotel Provincetown

698 Commercial St Provincetown MA
48.28 km from city center
Stay at this hotel in Provincetown. Enjoy free parking, an outdoor pool, and a fireplace in the lobby. Our guests praise the pool and the helpful staff in our ...
All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

1199 Route 28 South Yarmouth MA
31.45 km from city center
Book a stay at this business-friendly hotel in South Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Red Jacket Beach Resort

Red Jacket Beach Resort

1 South Shore Drive South Yarmouth MA
30.39 km from city center
Book a stay at this beach hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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