Sterling Vacation Packages 2026 from $382

Sterling flight + hotel vacation packages

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

The Wylie Inn and Conference Center at Endicott College

$382

per person

Apr 19 - Apr 23

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

A 24-hour gym, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A coffee shop, a computer station, and luggage storage are also on offer.

The Beverly

$509

per person

May 3 - May 8

found 20 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. Express check-out and a virtual front desk are also provided.

Eurostars The Boxer

West End

$669

per person

May 1 - May 3

found 10 hours ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. A computer station, dry cleaning, and luggage storage are also on offer.

Top Sterling hotels deals

Chocksett Inn and Restaurant

59 Laurelwood Road Sterling MA

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$189 total

Feb 9 - Feb 10

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-out, and wedding services are also on offer.

Pet friendly

Parking included

Great Wolf Lodge Boston / Fitchburg, MA

150 Great Wolf Dr Fitchburg MA

$179 nightly

$200 total

Feb 10 - Feb 11

Total with taxes and fees

This smoke-free resort features free water park access, 4 indoor pools, and a restaurant. Bring the family and enjoy the lazy river, bowling alley, and mini golf. Enjoy the seasonal outdoor pool and unwind at the bar/lounge and poolside bar.

Pool

Restaurant

The Colonial Hotel

625 Betty Spring Road Gardner MA

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$179 total

Feb 9 - Feb 10

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

DoubleTree by Hilton Hotel Boston - Westborough

5400 Computer Dr Westborough MA

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$118 total

Feb 22 - Feb 23

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Parking included

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

1360 Worcester St Natick MA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$119 total

Feb 22 - Feb 23

Total with taxes and fees

This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a snack bar/deli, and express check-in are also offered.

Pet friendly

Parking included

Embassy Suites by Hilton Boston Marlborough

123 Boston Post Rd W Marlborough MA

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$127 total

Feb 12 - Feb 13

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like cooked-to-order breakfast and free self parking.

Pool

Hot Tub

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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.

Mary Had a Little Lamb Statue

You can find out about the history of Sterling when you stop by Mary Had a Little Lamb Statue. Experience the area's festivals and entertainment venues.

Frequently asked questions

How much are vacation packages to Sterling?

Your vacation daydreams can be realized in Sterling from just $382. Our packages include flights and hotels, so they're bound to make booking nice and easy. The only thing you'll have to worry about is having an incredible time.

How long should my Sterling vacation be?

Many travelers pack their bags and explore the sights of Sterling for approximately 2 nights. That's a good starting point, but don't feel restricted by it. Whether you stay a couple of nights to see the famous sights or hang around to discover the lesser-known sights, an unforgettable adventure awaits.

Where can I get the best vacation package deals for Sterling?

You can grab terrific Sterling package deals with Travelocity. Choose from as many as 400 airlines and 1,000,000 properties worldwide and turn those travel dreams into reality.

Why should I book my Sterling vacation package with Travelocity?

Travel is all about making fantastic new memories and leaving all your troubles behind — which is why we have a team of experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our broad range of package deals. So what are you waiting for? There's no time like the present to secure that vacation you've always dreamed of.

Can I save on my Sterling car rental if I book it with hotels and flights?

Bundling your hotel, flight and car into a Sterling vacation package is a surefire way to land the best deal. Plus, having your own car rental gives you total freedom to find your way to all those big sights you can't wait to check out. Located 35 mi from Sterling, Fenway Park is one attraction that should feature on your itinerary. Fasten your seat belt and make a day trip of it.

Which airport is best for Sterling?

Logan Intl. Airport (BOS) (40 mi away from downtown), Bradley Intl. Airport (BDL) (60 mi away from central Sterling) and T.F. Green Airport (PVD) (50 mi away from central Sterling) are the main options in Sterling.

Where should I stay when visiting Sterling?

Many travelers stay at the Chocksett Inn and Restaurant. It's the perfect base for your Sterling escape.