Sterling Holidays from £848

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Your Sterling Holiday

Our Sterling holiday packages offer countless opportunities to discover new sights, sounds and sensations. And with all the planning taken care of, you can relax and enjoy your city break in the way that you deserve. Tower Hill Botanic Garden, Museum of Russian Icons and Dexter Drumlin are just a few of the sights worth exploring during your trip to Sterling. Expedia is here to help you escape the everyday. Tailor your holiday to Sterling to suit your style of travel, whatever that may be.

Top Sterling Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on 3 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
27 Oct - 3 Nov
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
Raffles is the most service oriented hotel we have ever stayed at. This place is amazing!!

Reviewed on 2 Aug 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
8 Sept - 14 Sept
found 12 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (358 reviews)
The property wasn’t at the level we expected of the Mandarin Oriental, however the location was good and walkable to Bay Bay restaurants and shopping.

Reviewed on 4 Aug 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
27 Oct - 3 Nov
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9/10 Wonderful! (2,696 reviews)
The staff really go above and beyond in customer service no questions were left unanswered, and assistance with finding our way around Boston. Special shout out to Maya, she really was helpful and considerate of our needs. Loved the property location which made our first time in Boston so much more special. If we are ever back in the area we would not hesitate to stay here again. Thanks again

Reviewed on 4 Aug 2025

Sterling Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
7,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Wachusett Mountain Ski Area, Apex Entertainment Centre and Worcester Art Museum

Top hotels in Sterling

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 out of 5
59 Laurelwood Road, Sterling, MA
The price is £159 per night from 10 Aug to 11 Aug
£159
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (132 reviews)
Short Stay
"Everything went smoothly, but for the noisy air conditioning system and the very noisy toilet!!! Other than that nice, clean, no disturbances at all."

Reviewed on 25 Jun 2025

Chocksett Inn and Restaurant
Extended Stay America Suites Boston Westborough Computer Dr

Extended Stay America Suites Boston Westborough Computer Dr

2.5 out of 5
1800 Computer Dr, Westborough, MA
Fully refundableReserve now, pay when you stay
The price is £78 per night from 11 Aug to 12 Aug
£78
11 Aug - 12 Aug
includes taxes & fees
6.4/10 (909 reviews)
"Good"

Reviewed on 18 Jul 2025

Extended Stay America Suites Boston Westborough Computer Dr
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
5400 Computer Dr, Westborough, MA
Fully refundableReserve now, pay when you stay
The price is £100 per night from 14 Aug to 15 Aug
£100
14 Aug - 15 Aug
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"The restaurant staff is exceptional."

Reviewed on 4 Aug 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 356 properties in Sterling
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

Why should I book my Sterling holiday with Expedia?
With top-value flights, hotel and car hire choices all in one place, Expedia makes booking your Sterling holiday hassle-free. What's more, we can help you bundle your bookings into a package holiday so you can get even more savings. Choose from amazing properties, add your flights and/or a car hire (and maybe even some exciting activities!) and get incredible prices. Need to change your plans? Expedia offers a flexible cancellation policy for many bookings. To discover more, check out our Customer Service Portal link.
When is the best time of year to holiday in Sterling?
February, June and October are the busiest months in Sterling, while May, November and December are generally quieter. Plan your getaway to Sterling based on what style of holiday you want. January is the coolest month, when average daytime temperatures are -3ºC. In July, the warmest period, you can expect averages of 22ºC during the day.
What is the top hotel for my holiday in Sterling?
Offering many of home's creature comforts, Boston Park Plaza will make the perfect base for your Sterling escape.
How do I get a cheap holiday to Sterling?
Browse and book everything all in one place with our Sterling holidays. You'll discover bargains on flights, hotels and more that'll keep your credit card happy and your adventurous spirit alive. And, with more than 400 partner airlines and 321,000 hotel options throughout the world to select from, you have countless opportunities to mix and match as you please. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Sterling holiday?
Make sure your next holiday in Sterling is one to remember by checking out its leading attractions. Wachusett Mountain Ski Area, Tower Hill Botanic Garden, Polar Express and Nashoba Valley Winery are some of the things worth discovering while you're in this city.
Do I need a visa for my Sterling holiday?
Visa requirements for Sterling vary based on your nationality and purpose of your visit. Make sure you check official government websites to determine if you need a visa for your holiday. They'll give you the most up-to-date information, including details about application procedures or supporting documentation that may be necessary. Research your visa requirements well ahead of time to ensure a travel experience that's hassle free. Finally, check to see that your passport has a minimum of six months validity from your planned date of return.
What should I wear on my Sterling holiday?
Do some research into the sorts of clothing people in Sterling wear, and consider browsing social media fashion pages for inspiration. Whatever your look, try to create a versatile wardrobe full of pieces that work for your destination and showcase your personal style. Daytime temperatures during January, Sterling's coolest month, average -3ºC. July marks this city's warmest month when the average temperature reaches 22ºC. Our top piece of advice? Take the guesswork out of packing and check the local weather conditions.
What does an Expedia Sterling holiday include?
Flights, hotels and car hires, or any combination of them — it's totally up to you. Whether you're visiting Sterling with the kids or enjoying a solo break, there's a package to match your budget and style. Once you've made your booking, why not add on a few tours or activities? Explore a large selection of property types and select one that matches your travel needs. The most in-demand rentals here are private holiday homes and apartments. With Expedia, it's a breeze to tailor your Sterling retreat however you want.
Does Expedia offer Book Now, Pay Later Sterling holidays?
Expedia has teamed up with online lender Klarna to make booking your next getaway easier on your budget. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more money to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that work for all budget sizes, so you can take that well-deserved holiday sooner.
  • No-deposit holidays: When you stumble on an awesome deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.

Can I choose my airline with a Sterling Expedia holiday?
Yes, so take your pick! We have access to over 400 airlines globally, so you can customise your Sterling adventure according to your budget and style.

* 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.