Sterling Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Sterling

Price found within the past 48 hours. Click for updated prices.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
10 Sept - 13 Sept
found 21 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Located in a new neighborhood with lots of dining options and easy access to public transportation.

Reviewed on 28 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
10 Sept - 13 Sept
found 21 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 21 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 21 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,964 reviews)
Great stay. Rooftop pool and easy access to multiple T stops for walking. Only complaint was the shower had water underneath the tub and it inpacted our ability to shower before dinner. However maintenance quickly resolved the issue, although with only a short term fix.

Reviewed on 27 Jul 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
10 Sept - 13 Sept
found 21 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
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Reviewed on 28 Jul 2025

Top hotels in Sterling

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 out of 5
59 Laurelwood Road, Sterling, MA
Fully refundableReserve now, pay when you stay
The price is €180 per night from 30 Jul to 31 Jul
€180
30 Jul - 31 Jul
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
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd, Framingham, MA
Fully refundableReserve now, pay when you stay
The price is €88 per night from 30 Jul to 31 Jul
€88
30 Jul - 31 Jul
includes taxes & fees
6.8/10 (1,020 reviews)
"Fine but in decline . Could be better . I have no specific concerns"

Reviewed on 26 Jul 2025

Motel 6 Framingham, MA - Boston West
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 €113 per night from 4 Aug to 5 Aug
€113
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (1,018 reviews)
"Great stay, location and breakfast!"

Reviewed on 22 Jul 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 354 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.

Frequently asked questions

How much does a Sterling holiday package cost?
You'll find cheap prices from €546 on Expedia for your Sterling escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your holiday to Sterling costs.
What are the cheapest months to go to Sterling?
The off-season is the best time to visit Sterling if you're trying to save. Another tip for finding cheap Sterling holiday packages? Avoid visiting during public holidays and any major events.
How many days is enough for Sterling?
With a well-planned itinerary, you can easily hit the top Sterling attractions in a handful of days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Sterling holiday for longer.
How to find the best Sterling package deals?
Use Expedia's handy filters to help you find some of the best Sterling package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Sterling package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Sterling holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a tailored Sterling holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Sterling?
Land incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Sterling holiday.
How to plan a trip to Sterling?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Sterling.
  2. Set your budget: Consider costs like flights, food and transportation when calculating how much to set aside for your trip to Sterling. Then, choose a property that fits your budget, whether that's an economical stay or a more upscale getaway.
  3. Determine how many days away: Start by making a list of all the sights and activities you'd like to get to in Sterling. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Sterling holiday package that brings all your bookings together.

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