Orient Heights Vacations from $531

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Your Orient Heights Vacation

Take all the hassle out of organizing your next break by booking an Orient Heights vacation package. Soak in the sights and sounds of this wonderful neighborhood and enjoy all it has to offer. When it's time to head out and explore, you'll find a lot of popular attractions nearby including USS Constitution Museum, New England Aquarium and Paul Revere House. Visit one, two or all during your trip to Orient Heights. Don't just think about it — make it happen! Reserve your ultimate Orient Heights vacation with Expedia and experience travel your way.

The Latest Orient Heights Vacation Packages

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $861, price is now $531 per person
$531
per person
Aug 28 - Aug 31
found 3 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (188 reviews)
It is truly a bed and breakfast. We stayed in the main house in a cozy upstairs updated bedroom overlooking the ocean. Breakfast was served every morning between 8am and 10am. Allowing us to have our coffee and stroll along the beach before our meal. Staff friendly and helpful. We will return again next year

Reviewed on Jun 18, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $1,044, price is now $606 per person
$606
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Beachside Village Resort

Beachside Village Resort

3 out of 5
Save 100% on your flight
Price was $1,019, price is now $632 per person
$632
per person
Aug 28 - Aug 31
found 3 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (111 reviews)
This property was extraordinary. My late check-in was seamless, and my room was spacious and extremely comfortable. The staff (my apologies, I forgot the front desk staff's names) were friendly, helpful, and professional. I had one minor maintenance issue that Joe resolved promptly and courteously. My room was directly across from the water, so I had a great view from my room and balcony. Having a kitchen made me feel right at home. My local friends, etc., were extremely impressed by the property layout, location, and price. Downtown was within walking distance (about a mile), and the beach was nearby. I will definitely plan a return visit here, but it would be hard to top my last stay.

Reviewed on Jun 5, 2026

The Highliner Hotel

The Highliner Hotel

2 out of 5
Downtown Gloucester
Save 100% on your flight
Price was $1,791, price is now $1,167 per person
$1,167
per person
Sep 4 - Sep 9
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (5 reviews)
Excellent experience

Reviewed on Jun 5, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,816, price is now $1,200 per person
$1,200
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Where to stay in Orient Heights

Find the best Orient Heights areas and neighborhoods for the activities you enjoy most. Learn more about Orient Heights
Downtown Boston

Downtown Boston

4.5/5(2,438 area reviews)

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.

Find hotels in Downtown Boston

Orient Heights Hotel Deals

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $163 total per night from Jul 1 to Jul 2
$163 total
Jul 1 - Jul 2
Total with taxes and fees
9/10 Wonderful! (2,689 reviews)
"Great location"

Reviewed on Jun 21, 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$238 nightly
The price is $277 total per night from Jul 2 to Jul 3
$277 total
Jul 2 - Jul 3
Total with taxes and fees
9.2/10 Wonderful! (4,724 reviews)
"Great"

Reviewed on Jun 21, 2026

Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $254 total per night from Jul 5 to Jul 6
$254 total
Jul 5 - Jul 6
Total with taxes and fees
9.6/10 Exceptional! (4,459 reviews)
"Très bien situé à seaport"

Reviewed on Jun 21, 2026

Seaport Hotel Boston
See all 4,127 properties in Orient Heights
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Orient Heights

Fenway Park

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Gillette Stadium

Gillette Stadium

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

Gillette Stadium
Harvard University

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Harvard Guide leading a tour

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.