Deals on vacations and trips to Sterling

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Sterling flight + hotel vacation packages

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

The McKernan Inn

3 out of 5
Price was $732, price is now $510 per person
$510
per person
Mar 20 - Mar 24
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,807, price is now $1,150 per person
$1,150
per person
Feb 19 - Feb 23
found 23 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Save 100% on your flight
Price was $843, price is now $574 per person
$574
per person
Feb 26 - Mar 4
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 4 onsite conference rooms. A snack bar/deli and concierge services are also provided.
AC Hotel by Marriott Portsmouth

AC Hotel by Marriott Portsmouth

3.5 out of 5
North End
Save 100% on your flight
Price was $840, price is now $599 per person
$599
per person
Feb 26 - Mar 4
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A restaurant, a 24-hour front desk, and dry cleaning are also provided.
The Inn at Buzzards Bay

The Inn at Buzzards Bay

2.5 out of 5
Price was $903, price is now $669 per person
$669
per person
Mar 7 - Mar 14
found 3 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Boston (BOS)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, express check-out, and barbecue grills are also on offer.

Top Sterling hotels deals

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 out of 5
59 Laurelwood Road Sterling MA
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $178 total per night
$178 total
Dec 28 - Dec 29
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
Red Roof Inn Boston - Southborough/ Worcester

Red Roof Inn Boston - Southborough/ Worcester

2 out of 5
367 Turnpike Rd Southborough MA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $94 total per night
$94 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A picnic area is also provided.
Pet friendly
Parking included
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
Free Cancellation
$179 nightly
The price is $200 total per night
$200 total
Jan 4 - Jan 5, 2026
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 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
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $127 total per night
$127 total
Jan 1 - Jan 2, 2026
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
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd Framingham MA
Free Cancellation
$77 nightly
The price is $81 total per night
$81 total
Dec 28 - Dec 29
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.
Pet friendly
Parking included
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
5400 Computer Dr Westborough MA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $109 total per night
$109 total
Jan 2 - Jan 3, 2026
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
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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.

Davis' Farmland & Mega Maze

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.

Mary Had a Little Lamb Statue

Frequently asked questions

How much are vacation packages to Sterling?
Your vacation daydreams can be realized in Sterling from just $510. 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.

Photos of local treasures

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