Eastern Massachusetts Vacations from $1,185

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Eastern Massachusetts Vacation

Choose one of our vacation packages to Eastern Massachusetts and wander wherever your inner adventurer desires. Dining and culture are just a couple of the things you can look forward to in this exciting destination. Your trip to Eastern Massachusetts wouldn't be complete without experiencing some of its most well-known cities, starting with Boston. Two of the top attractions here include Fenway Park and TD Garden. Hyannis is another favorite city with Eastern Massachusetts travelers. Visitors to this exciting destination enjoy Cape Codder Water Park and Cape Cod Inflatable Park. From the instant you book your Eastern Massachusetts vacation to when you get back home, Expedia will be with you each step of the way.

The Latest Eastern Massachusetts vacation packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
Save 100% on your flight
$1,185
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9/10 Wonderful! (1,317 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
$1,447
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Great hotel at a terrific site. The North End restaurants and Faneuil Hall are both at walkable distances. Everywhere we were in the Hotel there was always a staff member asking if we needed help. We loved out stay at the Boston Harbor Hotel.

Reviewed on Sep 22, 2026

The Langham, Boston

The Langham, Boston

Downtown Boston
Save 100% on your flight
$1,354
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,007 reviews)
Nice place. Centrally located. N

Reviewed on Sep 22, 2026

Raffles Boston

Raffles Boston

Back Bay
Save 100% on your flight
$1,354
per person
Nov 11 - Nov 15
found 7 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.6/10 Exceptional! (312 reviews)
The room is beautiful, minimalist, luxurious, and extremely comfortable. In my opinion, it’s perfect for a solo traveler or, especially, for a couple. Since the room is on the smaller side, I personally wouldn’t consider it ideal for families traveling with children. For a romantic getaway, however, it was absolutely perfect. One of the highlights is having an incredible and highly sought-after restaurant right inside the building. The dining experience was exceptional — the food was impeccable, the atmosphere was beautiful, and it truly added another level to our stay. I highly recommend making the restaurant part of the experience. To make our stay even more special, I hired a local company, Our Love Box (@ourlovebox on Instagram), to create a romantic surprise in the room. I ordered a gorgeous bouquet of 100 roses along with a full romantic room setup, and the result was absolutely stunning. What impressed me even more was how seamless everything was. They handled the entire setup and came back the following day to remove all of the decorations. Once they were finished, you couldn’t even tell there had been a setup in the room — everything was left exactly as it was before. Overall, the entire experience was incredible. Between the luxurious and comfortable room, the exceptional dining experience, and the romantic setup, it was truly memorable. I highly recommend this experience for couples celebrating an anniversary, birthday, proposal, or simply looking for a special

Reviewed on Sep 21, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
$1,681
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.4/10 Exceptional! (484 reviews)
Don't see what you're looking for?
See all available trips from Boydton to Eastern Massachusetts
View all trips

Where to stay in Eastern Massachusetts

Find the best Eastern Massachusetts areas and neighborhoods for the activities you enjoy most. Learn more about Eastern Massachusetts
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

A historic building with ornate architecture, a staircase, and a tree in front.

Back Bay

1 out of top 10 points of interest in this area

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

A city skyline with modern high-rise buildings, a historic bridge, and a river with boats.

Seaport District

1 out of top 10 points of interest in this area

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.

A street lamp with a lit bulb, surrounded by trees and a brick building.

Beacon Hill

1 out of top 10 points of interest in this area

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.

A bustling riverside area with a prominent building featuring a large arched entrance, a dock with a boat, and a crowd of people.

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

Stay near popular Eastern Massachusetts attractions

A cityscape with a prominent stadium, a busy intersection, and a skyline with high-rise buildings.

Fenway Park

9.2/10 (11,009 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
See properties
A historic building with a clock tower, a large gate, and a well-maintained lawn.

Harvard University

9.2/10 (6,542 reviews)
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
See properties
A public park with a large fountain, surrounded by trees and modern buildings.

Boston Common

9.4/10 (18,299 reviews)
The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.
See properties
A soccer stadium with a crowd of spectators, a goalpost, and players in action.
Photo by The Curious Zephyr

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.
See properties
A modern building with 'GARDEN' signage, a waterfront, and a cable-stayed bridge.

TD Garden

9.2/10 (7,449 reviews)
Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.
See properties
A historic church with a pointed roof and a large tower, surrounded by modern buildings and a well-maintained park with flowers and trees.

Copley Square

9.4/10 (7,327 reviews)
Explore some of Boston’s finest buildings, educational and arts institutions, and shopping, or simply find a patch of grass and relax.
See properties
A historic town square with brick buildings, a red bus, and a Harvard sign.

Harvard Square

9.0/10 (3,936 reviews)
With a visit to Harvard Square, a favorite shopping spot in Cambridge, you can search for that perfect souvenir. Experience the fascinating museums and acclaimed art scene in this vibrant area.
See properties
A modern architectural building with a large overhanging roof and a glass facade.

Boston Convention and Exhibition Center

8.8/10 (2,207 reviews)
During your trip, find out what's happening at Boston Convention and Exhibition Center, a top convention center in Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.
See properties

What to do in Eastern Massachusetts

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

$50
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

$17
per traveler
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Eastern Massachusetts

Eastern Massachusetts Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$394 nightly
$459 total
Oct 2 - Oct 3
Total with taxes and fees
Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$304 nightly
$353 total
Oct 4 - Oct 5
Total with taxes and fees
Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$265 nightly
$308 total
Sep 27 - Sep 28
Total with taxes and fees
The Revolution Hotel
See all 16,050 properties in Eastern 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 Eastern Massachusetts Vacation Packages

Eastern Massachusetts Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)

More vacations you might like

Explore a world of travel with Expedia

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