Highlands Holidays from £1,098

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Your Highlands Holiday

Your next big journey is calling with a holiday package to Highlands. Fun, food and nonstop good times — you're bound to find it in this neighbourhood. Begin your trip to Highlands by heading to nearby attractions such as Bentley College, Brandeis University and Moody Street Historic District. Expedia can help you turn your ideal Highlands holiday into reality, no matter your budget or travel plans.

Price found within the past 48 hours. Click for updated prices.
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

2.5 out of 5
per person
27 Oct - 30 Oct
found 19 hours ago
Return flight included
London (LHR) to Boston (BOS)
9/10 Wonderful! (956 reviews)
It was very clean and beautifully kept. All staff were professional and nice.

Reviewed on 10 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
15 Sept - 22 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on 11 Aug 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
15 Sept - 22 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
15 Sept - 22 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8.6/10 Excellent! (2,132 reviews)
My first time here..The staff was very helpful and it was very clean.the room itself was a very great use of space..no refrigerators however ice machine literally on every floor was great. Coupsnt beat the price either. Quick walk to the concention center too . Came for fan expo.

Reviewed on 10 Aug 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
15 Sept - 22 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
8.8/10 Excellent! (1,021 reviews)
The bed was comfortable

Reviewed on 10 Aug 2025

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Downtown Boston which includes a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in Highlands

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £189 per night from 24 Aug to 25 Aug
£189
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,799 reviews)
"The best in the seaport!"

Reviewed on 9 Aug 2025

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £169 per night from 1 Sept to 2 Sept
£169
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (3,196 reviews)
"The staff is great! The valet were absolute gentlemen! The folks at the front desk were lovely and, when I was lost trying to find parking, the young lady on the phone made me feel at ease, gave perfect guidance and even rooted me on by saying "you can do this!" And I can't forget the concierge who ..."

Reviewed on 9 Aug 2025

Hilton Boston Park Plaza
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £168 per night from 17 Aug to 18 Aug
£168
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (1,567 reviews)
"Loves the property! Close to the subway!"

Reviewed on 7 Aug 2025

citizenM Boston Back Bay
See all 3,386 properties in Highlands
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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Highlands travel package cost?
From just £1,098. Yes, you read that correctly. Our Highlands travel packages are the easiest way to make your budget stretch further. Bundle your hotels, flights and rental car and explore this vibrant destination.
If I'm not able to travel, can I cancel my Highlands travel package?
Whether it's your hotel, flight or rental car, you can cancel or change it. Locked in your Highlands travel package in the last 24 hours? You may be able to make changes or cancellations for free. For bookings made more than 24 hours ago, you may incur a charge from your hotel, airline or car rental company. For more information, check out our Customer Service Portal. We'll help you every step of the way.
How do I get a cheap travel package to Highlands?
Browse and book everything in the one place with our Highlands travel packages. You'll discover deals on hotels, flights and more that'll keep your travel budget happy and your sense of adventure alive. And, with more than 550 partner airlines and 1,000,000 properties all over the world to select from, you'll have endless opportunities to mix and match however you please.
Does Expedia offer Book Now, Pay Later Highlands holidays?
Yes, we do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply choose the payment plan best suited to your needs during checkout and take away the stress of budgeting for your next trip. Remember to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your holiday buck. Check out our flexible payment options below:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's convenient monthly instalment plans. If making bite-sized repayments each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your holiday across multiple transactions.
  • Low deposit holidays: Pressing the "book now" button is easier with this plan. Put down a small deposit on your escape and then start packing your bags.

Where should I stay in Highlands?
Book a hotel nice and close to Bentley College, one of this neighbourhood's top attractions. It's the ideal place if you're looking to capture some great travel photos.
What are the top hotels in Highlands?
Lock in a room at Best Western Plus Waltham Boston. It's one of the area's most popular properties. Another top-rated option in Highlands is Hilton Garden Inn Boston/Waltham.
How far in advance should I book my Highlands holiday?
It all depends on the air carrier, but you can normally browse through international flights on Expedia up to 12 months in advance. While it's generally a good idea to book ahead of time, lucky travellers occasionally nab a cheaper flight just weeks prior to the date of departure.
What does an Expedia Highlands travel package include?
That depends on you. You can select from a variety of Highlands bundles, such as a hotel, rental car and flight. You can also book a flight with a hotel, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like activities and tours. Whatever your perfect Highlands holiday looks like, you're sure to save!
What should I know before booking a Highlands travel package?
A travel package can be easier on the wallet than separately booking everything you need for your adventure. For example, bundle your flights, hotels and rental cars and score impressive savings. Whatever sort of holiday you're planning, there's sure to be a package that matches your budget.
Can I choose my airline with a Highlands Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our travel packages give you the flexibility to pick from available flight, hotel or activity options that suit you.

Popular places to visit

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

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

Fenway Park
Harvard University showing a city and heritage architecture

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
Boston Common which includes a skyscraper, landscape views and a park

Boston Common

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.

Boston Common

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£59
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£52
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

£25
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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. Flight-inclusive packages are ATOL protected.