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Sterling Vacation Packages

Welcome to Sterling, Central Massachusetts. This region's charming rural landscapes and rolling hills draw in visitors of all sorts.

Save Time and Money with a Sterling Package Deal

Expedia enables you to save money when you purchase a package. We will help you and your traveling partner purchase your perfect flight and hotel combination. You'll have more spending money for your Sterling vacation!

Smart travelers who purchase a package deal can save up to $583.

With hefty savings and approximately 400 partner airlines and 321,000 hotels worldwide on our universal database, you should book today!

Imagine the extra money you'll have with some of the best prices and deals via Expedia.

You can postpone your travel plans with us because we do not charge cancellation fees for almost all of our hotel reservations.

Sterling Vacation Packages

Sterling is located around 35 miles away from Boston and about 45 miles from Providence.

While you're here, think about making the trip to West Newton to check out Harvard Square. To get there, travel 30 miles east of Sterling.

16 miles east of this place is Maynard. When you arrive there, stop at Walden Pond.

You'll be happy to hear that you have a number of scenic beaches at your fingertips. Oakland Beach, 55 miles to the south, and Crystal Lake Sandy Beach, 45 miles to the southwest, are two popular choices.

When you start to crave the sights and sounds of Mother Nature, round up the family and head to Callahan State Park, located 18 miles from Sterling. Also consider Ghiloni Park, 14 miles away.

Sports lovers should go see the Worcester Bravehearts or Holy Cross Crusaders at Fitton Field in Worcester, 14 miles to the south of Sterling. If you're fond of baseball, then this is the right place for you to be.

To ski on fresh powder slopes, make your way to Blue Hills Ski Area or Nashoba Valley Ski Area.

If you travel 4 miles to the east of Sterling you will get to South Lancaster. Some time here gives you the chance to visit Johnny Appleseed Visitor Center and Roller Kingdom. In addition, you could check out Solomon Pond Mall and The Silver Buffalo Gallery in Clinton. This destination sits 5 miles from Sterling.

About 5 miles to the west of Sterling is Princeton, an important regional center where you'll find Wachusett Mountain Ski Area, Redemption Rock and Monadnock Triple. Minuteman Express and Polar Express are some additional sites that ought to be on every traveler's to-do list.

Central Massachusetts offers plenty of cool ways to experience its alluring landscapes. Adventurous types should try hiking or horse riding.

Once you're packed and ready to get your flight, it's good to remember that the nearest airport is located 40 miles to the northeast.

Accommodation in Sterling

Visitors to Sterling should secure a hotel ahead, because currently there are only limited Sterling hotels available.

The Chocksett Inn and Restaurant and Classic Suites and Inn are your best options in Sterling.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Hotel Deals

See all 88 Properties in Sterling
Chocksett Inn and Restaurant $129
Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

59 Laurelwood Road, Sterling
     
    4.1
    of 5, from 32 reviews
    3.5 out of 5.0

    Situated in Sterling, this romantic hotel is within 12 mi (20 km) of The Mall at Whitney Field, Nashoba Valley Winery, and Wachusett Mountain Ski Area. Solomon Pond Mall is 12.8 mi (20.5 km) away.

    Red Roof PLUS+ Boston - Framingham
    Red Roof PLUS+ Boston - Framingham

    Red Roof PLUS+ Boston - Framingham

    650 Cochituate Rd, Framingham
       
      3.8
      of 5, from 1,503 reviews
      2.0 out of 5.0

      The hotel is within a half-hour drive of downtown Boston, and only minutes from New England's largest concentration of retail outlets. Natick Mall offers a huge range of shops and restaurants, and visitors can also try Ken's Steakhouse, a local institution just a mile from the hotel.

      Magnuson Hotel Framingham $75
      Magnuson Hotel Framingham

      Magnuson Hotel Framingham

      130 Worcester Rd, Framingham
         
        3.6
        of 5, from 1,002 reviews
        2.5 out of 5.0

        Situated in the business district, this hotel is within a 15-minute walk of Fun and Games Family Entertainment Center and Shoppers World. Natick Collection and Learned Beach are also within 2 mi (3 km).

        Best Western At Historic Concord $116
        Best Western At Historic Concord

        Best Western At Historic Concord

        740 Elm St, Concord
           
          4.3
          of 5, from 819 reviews
          2.5 out of 5.0

          This hotel is centrally located near the historic sights and attractions of New England, including the homes of Ralph Waldo Emerson and Louisa May Alcott, and Walden Pond.

          Days Inn by Wyndham Leominster/Fitchburg Area $68
          Days Inn by Wyndham Leominster/Fitchburg Area

          Days Inn by Wyndham Leominster/Fitchburg Area

          482 N Main St, Leominster
             
            3.0
            of 5, from 452 reviews
            2.0 out of 5.0

            Situated in Leominster, this motel is 2.2 mi (3.5 km) from The Mall at Whitney Field and within 6 mi (10 km) of Fitchburg State University and Johnny Appleseed Visitor Center. Wachusett Mountain Ski Area and Ashburnham Town Hall are also within 12 mi (20 km).

            Holiday Inn Express Hotel & Suites Auburn $104
            Holiday Inn Express Hotel & Suites Auburn

            Holiday Inn Express Hotel & Suites Auburn

            10-12 Johnson St, Auburn
               
              4.3
              of 5, from 678 reviews
              2.5 out of 5.0

              Situated in Auburn, this hotel is 1.2 mi (1.9 km) from Auburn Mall and 2.9 mi (4.6 km) from Goddard Rocket Launching Site. Clark University and Fitton Field are also within 6 mi (10 km).

              Courtyard by Marriott Boston Marlborough $87
              Courtyard by Marriott Boston Marlborough

              Courtyard by Marriott Boston Marlborough

              75 Felton St, Marlborough
                 
                4.3
                of 5, from 535 reviews
                3.0 out of 5.0

                Situated in Marlborough, this hotel is within a 15-minute walk of Peter Rice Homestead and Apex Entertainment Center. New England Sports Center and John Brown Bell are also within 3 mi (5 km).

                Hilton Garden Inn Worcester $118
                Hilton Garden Inn Worcester

                Hilton Garden Inn Worcester

                35 Major Taylor Boulevard, Worcester
                   
                  4.2
                  of 5, from 888 reviews
                  3.0 out of 5.0

                  Situated in Worcester, this hotel is within a 10-minute walk of DCU Center, Mechanics Hall, and Union Station. Franklin D. Roosevelt American Heritage Center and Worcester Historical Museum are also within 15 minutes.