Sterling Vacation Packages 2026 from $518

Sterling flight + hotel vacation packages

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

Holiday Inn Express Fall River North by IHG

$518

per person

May 6 - May 11

found 14 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-in. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,770

per person

Apr 2 - Apr 7

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

The Wylie Inn and Conference Center at Endicott College

$521

per person

May 9 - May 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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 Langham, Boston

Downtown Boston

$977

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.

The Club at New Seabury

New Seabury

Save 100% on your flight

$745

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

A golf course, 2 restaurants, and 15 outdoor tennis courts are all featured at this smoke-free condo resort. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas. Enjoy the gym and unwind at the bar/lounge and beach bar.

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

Mar 1 - Mar 2

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

Embassy Suites by Hilton Boston Marlborough

123 Boston Post Rd W Marlborough MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$121 total

Mar 8 - Mar 9

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

Great Wolf Lodge Boston / Fitchburg, MA

150 Great Wolf Dr Fitchburg MA

Free Cancellation

$179 nightly

$200 total

Mar 2 - Mar 3

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

DoubleTree by Hilton Hotel Boston - Westborough

5400 Computer Dr Westborough MA

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$118 total

Mar 6 - Mar 7

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

Red Roof Inn PLUS+ Boston - Framingham

650 Cochituate Rd Framingham MA

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$90 total

Mar 2 - Mar 3

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.

Pet friendly

Parking included

Comfort Inn Auburn - Worcester

426 Southbridge St Auburn MA

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$94 total

Mar 3 - Mar 4

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-in. There's a gym on site, and a fireplace in the lobby and express check-out are also provided.

Breakfast included

Parking included

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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 $518. 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.