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Chestnut Hill Vacations

Pack those stellar shades. We have Chestnut Hill vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Chestnut Hill – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Chestnut Hill vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Chestnut Hill

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Chestnut Hill vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Chestnut Hill well.

Top Hotel Deals

See all 66 Properties in Chestnut Hill
Best Western Plus Towson Baltimore North Hotel & Suites

Best Western Plus Towson Baltimore North Hotel & Suites

1100 Cromwell Bridge Rd, Towson
    3.0 out of 5.0
     
     

    Located right off highway I-695, Best Western Plus Towson Baltimore North Hotel & Suites is a 3-minute drive from Towson Town Center mall. There are 3 golf courses ...

    Best Western Plus Towson Baltimore North Hotel & Suites$85

    Best Western Plus Towson Baltimore North Hotel & Suites$85
    Home2 Suites by Hilton Baltimore/White Marsh

    Home2 Suites by Hilton Baltimore/White Marsh

    10465 Philadelphia Road, White Marsh
      2.5 out of 5.0
       
       

      Situated in the entertainment district, this hotel is 2.2 mi (3.6 km) from White Marsh Mall and within 12 mi (20 km) of Double Rock Park and Boordy Vineyards. ...

      Home2 Suites by Hilton Baltimore/White Marsh$110

      Home2 Suites by Hilton Baltimore/White Marsh$110
      Red Roof PLUS+ Baltimore North - Timonium

      Red Roof PLUS+ Baltimore North - Timonium

      111 W Timonium Rd, Lutherville Timonium
        2.5 out of 5.0
         
         

        Situated in Lutherville Timonium, this hotel is within 6 mi (10 km) of Greenspring Station, Towson University, and Greater Baltimore Medical Center. Towson Town ...

        Red Roof PLUS+ Baltimore North - Timonium$62

        Red Roof PLUS+ Baltimore North - Timonium$62
        Comfort Inn Baltimore East Towson

        Comfort Inn Baltimore East Towson

        8801 Loch Raven Blvd, Towson
          2.5 out of 5.0
           
           

          Located in the heart of Towson, this hotel is 2.3 mi (3.8 km) from Goucher College and 2.8 mi (4.4 km) from Towson University. Towson Town Center and Mount Pleasant ...

          Comfort Inn Baltimore East Towson$72

          Comfort Inn Baltimore East Towson$72
          Days Inn by Wyndham Towson

          Days Inn by Wyndham Towson

          8712 Loch Raven Blvd, Towson
            2.0 out of 5.0
             
             

            Situated in Towson, this hotel is 2.4 mi (3.8 km) from Goucher College and 2.7 mi (4.3 km) from Towson University. Towson Town Center and Mount Pleasant Golf ...

            Days Inn by Wyndham Towson$55

            Days Inn by Wyndham Towson$55
            Hilton Garden Inn Baltimore/White Marsh

            Hilton Garden Inn Baltimore/White Marsh

            5015 Campbell Boulevard, Baltimore
              3.0 out of 5.0
               
               

              Situated in the entertainment district, this hotel is 0.7 mi (1.1 km) from White Marsh Mall and within 9 mi (15 km) of Double Rock Park and Mount Pleasant Golf ...

              Hilton Garden Inn Baltimore/White Marsh$84

              Hilton Garden Inn Baltimore/White Marsh$84
              Red Roof Inn Aberdeen

              Red Roof Inn Aberdeen

              988 Hospitality Way, Aberdeen
                2.0 out of 5.0
                 
                 

                Situated in a shopping district, this hotel is 1.7 mi (2.8 km) from Ripken Stadium and 1.8 mi (3 km) from Cal Ripken Museum. Aberdeen Proving Ground and Bulle ...

                Red Roof Inn Aberdeen$59

                Red Roof Inn Aberdeen$59
                Embassy Suites by Hilton Baltimore Hunt Valley

                Embassy Suites by Hilton Baltimore Hunt Valley

                213 International Cir, Hunt Valley
                  3.5 out of 5.0
                   
                   

                  Situated in Hunt Valley, this hotel is 1.5 mi (2.5 km) from Oregon Ridge Nature Center and within 9 mi (15 km) of Basignani Winery and Greenspring Station. Pine ...

                  Embassy Suites by Hilton Baltimore Hunt Valley$110

                  Embassy Suites by Hilton Baltimore Hunt Valley$110
                  Red Lion Hotel North Baltimore

                  Red Lion Hotel North Baltimore

                  2004 Greenspring Dr, Lutherville Timonium
                    3.0 out of 5.0
                     
                     

                    Situated in the business district, this hotel is within 6 mi (10 km) of Greenspring Station, Towson University, and Greater Baltimore Medical Center. Towson ...

                    Red Lion Hotel North Baltimore$81

                    Red Lion Hotel North Baltimore$81
                    Ramada Limited Cockeysville

                    Ramada Limited Cockeysville

                    10100 York Rd, Cockeysville
                      2.0 out of 5.0
                       
                       

                      Situated in Cockeysville, this hotel is within 6 mi (10 km) of Fire Museum of Maryland, Oregon Ridge Nature Center, and Hampton National Historic Site. Towson ...

                      Ramada Limited Cockeysville$59

                      Ramada Limited Cockeysville$59

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.