Sterling Vacation Packages 2026 from $609

Sterling flight + hotel vacation packages

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

Deerfield Inn

Save 100% on your flight

$609

per person

Sep 3 - Sep 7

found 15 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

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 lobby fireplace, a communal living room, and a computer station are also on offer.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,084

per person

Aug 31 - Sep 3

found 1 day ago

Roundtrip flight included

Austin (AUS) 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 Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

Save 100% on your flight

$4,158

per person

Aug 26 - Sep 1

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A private beach and a hot tub are featured at this guesthouse. Enjoy a day at the beach kayaking, or relax with sun loungers. WiFi in public areas is free.

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

$1,439

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$1,190

per person

Sep 15 - Sep 20

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out 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

$159 nightly

$178 total

Jul 19 - Jul 20

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

$149 nightly

$166 total

Jul 19 - Jul 20

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

Best Western Royal Plaza Hotel & Trade Center

181 Boston Post Rd W Marlborough MA

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$128 total

Jul 26 - Jul 27

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference center. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Pool

Breakfast included

La Quinta Inn by Wyndham Auburn Worcester

446 Southbridge St Auburn MA

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$83 total

Aug 9 - Aug 10

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's express check-out and multilingual staff can provide around-the-clock assistance.

Breakfast included

Pet friendly

DoubleTree by Hilton Hotel Boston - Westborough

5400 Computer Dr Westborough MA

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$137 total

Aug 16 - Aug 17

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

Monticello Inn Framingham

90 Worcester Rd Framingham MA

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$89 total

Jul 19 - Jul 20

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Parking included

Free WiFi

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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.

Stay near popular Sterling attractions

Davis' Farmland & Mega Maze

7.0/10 (2 reviews)

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

See properties

Frequently asked questions

How much are vacation packages to Sterling?

Your vacation daydreams can be realized in Sterling from just $609. 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.