Sterling Holidays

Book a Hotel + Flight or Car together to unlock savings

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 4.955.769 ₫ per night from 12 Aug to 13 Aug
4.955.769 ₫
5.535.515 ₫ total
12 Aug - 13 Aug
includes taxes & fees
8.6/10 Excellent! (133 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 2.430.424 ₫ per night from 12 Aug to 13 Aug
2.430.424 ₫
2.714.660 ₫ total
12 Aug - 13 Aug
includes taxes & fees
6.4/10 (914 reviews)
"Excellent staff"

Reviewed on 5 Aug 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 3.125.543 ₫ per night from 17 Aug to 18 Aug
3.125.543 ₫
3.491.232 ₫ total
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Have stayed here several times plan on returning. Had an ussuewith TV whi"

Reviewed on 10 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.

Popular places to visit

Davis' Farmland & Mega Maze

Enjoy an outing to Davis' Farmland & Mega Maze during your stay in Sterling. You can attend a sporting event while in the area.

Davis' Farmland & Mega Maze

Frequently asked questions

How much does a Sterling holiday package cost?
You'll find cheap prices 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.