Sterling Vacations from $322

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Your Sterling Vacation

Our Sterling vacation 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 vacation to Sterling to suit your style of travel, whatever that may be.

The Latest Sterling vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $560, price is now $322 per person
$322
per person
Dec 26 - Dec 31
found 21 hours ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
18.4/10 Exceptional! (1,111 reviews)
Overall-it was great! Bummer that the microwave on my floor didn't work. Not having a coffee maker in the room was fine, there's a little area on each floor with Keurigs (no cream, just grab that from the lobby when you check in)

Reviewed on Nov 20, 2025

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Price was $1,646, price is now $848 per person
$848
per person
Feb 12 - Feb 17
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
18.8/10 Exceptional! (460 reviews)
I haven’t stayed in a hotel this amazing for a long while! Everything about it was perfect, the staff, the facilities, the location / we had a room with a small kitchen area for a week and it was worth it. We hardly saw any other guests, and definitely didn’t hear anyone / it was a fantastic stay, had the gym to myself and there’s laundry facilities on most floors, I honestly didn’t want to leave! I would highly recommend to anyone visiting the area. The area itself has tons of shops and restaurants and feels very safe.

Reviewed on Nov 20, 2025

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,197, price is now $674 per person
$674
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
17.2/10 Exceptional! (1,337 reviews)
Staff were very courteous! Clean room!

Reviewed on Nov 15, 2025

Lakeside Inn

Lakeside Inn

2 out of 5
Save 100% on your flight
Price was $683, price is now $395 per person
$395
per person
Feb 12 - Feb 17
found 9 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
15.2/10 Exceptional! (2,303 reviews)
Great value right on lakefront and super nice staff!!

Reviewed on Nov 16, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,618, price is now $949 per person
$949
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
19.2/10 Exceptional! (482 reviews)
The room was wonderful, the bed was heaven. Room service was delicious and the overall aesthetic and ambience of the lobby and common areas were fabulous

Reviewed on Nov 18, 2025

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Discover the most popular places to visit in Sterling

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

Sterling Hotel Deals

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
$159 nightly
The price is $178 total per night from Nov 23 to Nov 24
$178 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (141 reviews)
Clean and comfortable

Reviewed on Oct 28, 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 refundable
$83 nightly
The price is $87 total per night from Nov 23 to Nov 24
$87 total
Nov 23 - Nov 24
Total with taxes and fees
6.6/10 (1,083 reviews)
Friendly staff

Reviewed on Nov 16, 2025

Motel 6 Framingham, MA - Boston West
The Verve Hotel Boston Natick, Tapestry Collection by Hilton

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

3.5 out of 5
1360 Worcester St Natick MA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $122 total per night from Nov 23 to Nov 24
$122 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Room a good temp, quiet, and comfortable.

Reviewed on Nov 16, 2025

The Verve Hotel Boston Natick, Tapestry Collection by Hilton
See all 368 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.

Find the Best Sterling Vacation Packages

Sterling Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
7,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Apex Entertainment Center, Wachusett Mountain Ski Area and Worcester Art Museum

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Frequently asked questions

How much does a Sterling vacation package cost?
You'll find cheap prices from $322 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 vacation to Sterling costs.
What are the cheapest months to go to Sterling?
If you're hoping to score a cheap Sterling vacation package, consider visiting in May, November and December. You'll generally find lower prices on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Sterling?
With a well-organized schedule, you can easily visit the top Sterling sights in a handful of days. But if you prefer to explore off the beaten track or go on day trips, think about booking your Sterling vacation 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 vacation package as early as possible.
Is it cheaper to book a Sterling vacation as a package?
Expedia vacation 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 vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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 vacation.
Does Expedia offer Book Now, Pay Later Sterling vacation packages?
Secure your dream getaway to Sterling with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for the next payday — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snap up cheap deals before they disappear.

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