Orient Heights Vacations from $743
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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
Save 100% on your flight
Price was $1,291, price is now $743 per person
$743
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The property was well maintained and close to good restaurants. We had a cooked breakfast every day.
Reviewed on Jul 16, 2026
Boston Lodge and Suites
Dorchester
Save 100% on your flight
Price was $2,339, price is now $1,310 per person
$1,310
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Good Hotels Boston
South End
Save 100% on your flight
Price was $2,032, price is now $1,183 per person
$1,183
per person
Sep 24 - Sep 29
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
Summer House Hotel
Save 100% on your flight
Price was $2,602, price is now $1,680 per person
$1,680
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
7.4/10 Good! (3 reviews)
Helpful staff! Make sure to review the check in information, there is a specific window of time! My room and bed were absolutely cozy and cute. I’d advise against staying in a cottage close to the restaurant in the summer if you are looking for absolute quiet due to the fact some are in immediate proximity to the outdoor dining area. Overall amazing stay, especially being so close to a beach with attached dining!
Reviewed on Jul 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
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.
Orient Heights Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $254 total per night from Aug 2 to Aug 3
$254 total
Aug 2 - Aug 3
Total with taxes and fees
9.6/10 Exceptional! (4,567 reviews)
"Great staff, great location. Clean room - overall great stay"
Reviewed on Jul 17, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $185 total per night from Aug 16 to Aug 17
$185 total
Aug 16 - Aug 17
Total with taxes and fees
9/10 Wonderful! (2,741 reviews)
"We enjoyed our 2 night stay at the Revolution. Short walk to Back Bay station put the entire city at our fingertips."
Reviewed on Jul 17, 2026
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $190 total per night from Aug 16 to Aug 17
$190 total
Aug 16 - Aug 17
Total with taxes and fees
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.
Things to do
Boston Haunted Tour : Ghosts & Gravestones
$47
per adult
80% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
Boston Summer Nights Tour and River Cruise
$50
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.