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.
Omni Parker House

Omni Parker House

Downtown Boston
Save 100% on your flight
$1,016
per person
Oct 29 - Nov 3
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Faneuil Hall Marketplace and Boston Common are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

North End
$1,463
per person
Oct 29 - Nov 3
found 11 hours ago
Roundtrip flight included
Chicago (ORD) 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
$1,351
per person
Sep 24 - Sep 28
found 10 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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

Hotel AKA Boston Common

Hotel AKA Boston Common

Downtown Boston
Save 100% on your flight
$1,080
per person
Oct 29 - Nov 3
found 11 hours ago
Roundtrip flight included
Chicago (ORD) 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 Boston Common and Faneuil Hall Marketplace are located nearby.
Great staff, Saheed was pleasant and courteous. Lovely room, clean and nice modern furniture. The staff in the restaurant are very attentive and friendly, the bartender Kathleen made excellent mixed drinks and was pleasant to talk to.

Reviewed on Aug 14, 2026

Eurostars The Boxer

Eurostars The Boxer

West End
Save 100% on your flight
$1,062
per person
Oct 29 - Nov 3
found 11 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
Save 100% on your flight
$1,253
per person
Oct 29 - Nov 3
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
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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. ...
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. ...
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. ...
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 ...
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 ...
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. ...
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 ...
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 ...
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 ...
The Beachside

The Beachside

30 North Beach Street Nantucket MA
63.06 km from city center
Stay at this hotel in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Jethro Coffin House and Children's Beach are located ...
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

180 Water St Plymouth MA
26.11 km from city center
Book a stay at this business-friendly hotel in Plymouth. Enjoy free parking, free water park access, and a 24-hour fitness center. Our guests praise the pool ...
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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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