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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,346, price is now $645 per person
$645
per person
Nov 9 - Nov 12
found 17 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,842, price is now $1,639 per person
$1,639
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,609, price is now $1,052 per person
$1,052
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,989, price is now $1,317 per person
$1,317
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $1,958, price is now $1,370 per person
$1,370
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

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
Oct 6 - Oct 7
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
Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

2 out of 5
1668 Worcester Rd Framingham MA
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $117 total per night
$117 total
Oct 26 - Oct 27
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
Courtyard by Marriott Boston Natick

Courtyard by Marriott Boston Natick

3 out of 5
342 Speen St Natick MA
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $118 total per night
$118 total
Oct 8 - Oct 9
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and express check-in are also offered.
Pet friendly
Free WiFi
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
$187 nightly
The price is $209 total per night
$209 total
Oct 4 - Oct 5
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
Courtyard by Marriott Boston Marlborough

Courtyard by Marriott Boston Marlborough

3 out of 5
75 Felton St Marlborough MA
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $151 total per night
$151 total
Oct 29 - Oct 30
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 gym and perks like free self parking and a free area shuttle.
Pool
Pet friendly
La Quinta Inn by Wyndham Auburn Worcester

La Quinta Inn by Wyndham Auburn Worcester

3 out of 5
446 Southbridge St Auburn MA
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $97 total per night
$97 total
Nov 1 - Nov 2
Total with taxes and fees
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 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
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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 $645. 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

Browse Sterling vacation photos for more inspiration

An aerial view of a town surrounded by dense forests, with a mix of residential and commercial buildings, and a prominent church.
A snow-covered town with a church, houses, and a road.
A white church with a steeple and clock tower, surrounded by trees and a well-maintained lawn.
Sterling Town Hall, a white building with a triangular pediment and columns.

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