View on map

Add to planner

KEY - Click on the boxes to filter the results shown on the map

  • Chatham

    Chatham is located at the southeast tip of Massachusetts and half way down the 75 mile long Cape Cod Peninsula. Cool summer sea breezes, warm Indian summers, and mild winters make Chatham a place to holiday year-round.

    • Chatham Beach


    • Beach House in Chatham


    Chatham is located at the southeast tip of Massachusetts and half way down the 75 mile long Cape Cod Peninsula. To the east is the Atlantic Ocean, to the South is Nantucket Sound, to the north is Pleasant Bay. Cool summer sea breezes, warm Indian summers, and mild winters make Chatham a place to vacation year-round.

    Whether you are an avid fisherman or a boater, Chatham is your homeport to the ocean. Take a seal tour or watch them follow the fishing fleet into the Chatham Fish Pier. If the water is not your thing, relax on the beach with miles of pristine white sand.

    Chatham is blessed with beautiful scenery, and offers many Nature Trails and Parks for biking and hiking. If golf is your passion, there are beautiful golf courses overlooking the Altantic.

    If you enjoy visiting historic places and museums, there are some of the best preserved homes and buildings in the area. The Old Village protects more than 300 historic properties.

    Chatham is well known for its fresh fish and seafood. While many restaurants feature the “catch of the day” and other local favorites, there is no lack of other fare, including Italian, French, Continental, Asian and, of course, good old traditional American.

    10 things to do in Chatham

    1. EAT SEAFOOD - Fresh seafood can define your vacation on Cape Cod, Chatham’s active pier ensures you dine on the freshest! Everything from fried seafood sandwiches at the pier (Chatham Pier Fish Market), to a foodie heaven overlooking the Chatham Municipal Airport’s tarmac (Hanger B Eatery), to fine dining at Impudent Oyster awaits your taste buds satisfaction.
    2. SHOP - Filled with Mom and Pop shops and bursting with character, Chatham’s Main Street is a do not miss while visiting Cape Cod. If you detour down some of the side streets you will see some noteworthy cottages and mansions. There are 5 great Main Streets for strolling and shopping on Cape Cod and Chatham is one of them.
    3. RIDE - At the Harwich bike rotary you can branch off the Cape Cod Rail Trail onto the Old Colony Rail Trail and it will lead you right into the heart of Chatham. Pass a refreshing Ice Cream shop, a foodie lunch stop at Hanger B Eatery, and maybe take a swim at White Pond along the way. For things to do in Chatham, it doesn’t get much more Cape Cod than this!
    4. SEE THE LIGHT - Start at the easy to reach, drive up and park, Chatham Light overlooking the stunning Lighthouse Beach. If you like to get off the beaten path a bit, take an easy 20 minute hike from Harding’s Beach to the formidable Stage Harbor Light. It is the 'secret' lighthouse of Chatham.
    5. SAIL - Leave from Stage Harbor on the adventure of a lifetime. Chatham is where our charter boat captain heads out each day for private Whale Watching, Sportfishing, and Shark Watching adventures. Empty your bucket list one great experience at a time, on Cape Cod.
    6. CHATHAM PIER - Head to the Chatham Pier if you want to see what’s being served tonight at the best restaurants on Cape Cod. Better yet, if you are looking for one of the best lunch spots in Chatham, the Chatham Pier Fish Market is right behind you. While you are there you are sure to spot the fisherman’s nemesis, the Seal.
    7. BEACHES - The water seems bluer around Chatham and the beaches are spectactular! Great for long walks and sightseeing, not so much for swimming. There are thousands of seals to spot off the coast of Chatham.
    8. SHARK CENTRE - The men in grey suits are so prevalent, in fact, that they have their own research center! The Atlantic White Shark Conservancy Centre is in Chatham and offers some astounding facts and presentations about these incredible, apex predators.
    9. ELDREDGE LIBRARY - While it may seem a waste while on vacation, the Eldredge Library in Chatham is an astonishing example of a classic library from the past. If you are on Cape Cod and a storm blows through or you are here to enjoy the shoulder season…it’s a perfect time to check out a beautifully restored library.
    10. SWIM - There are lots of great swimming holes around Chatham. A favorite is White Pond, conveniently located right off the Old Colony Rail Trail and perfect for a refreshing swim.
    Add this City to planner
    • Top Tip 1

      Catch the Boston Red Sox in a game of baseball at their famous Fenway Park, which celebrated its millennium in 2012. Soak up the friendly but electric atmosphere as you try to work out the rules of the game!

    • Top Tip 2

      Shopaholics should head to Boston’s Faneuil Hall Marketplace for big-name as well as eclectic stores or to Newbury Street, the most exclusive shopping street in New England. Here you’ll find unique art and craft galleries, jewellery outlets and boutiques.

    • Top Tip 3

      Cape Cod is one of the best places for a whale-watching boat trip (the season is from May to October). You may see dolphins as well as Humpback, Minke and Finback whales.

    • Top Tip 4

      Escape the crowds on the more remote beaches of the Cape Cod National Seashore coastline. Or, take the foot passenger ferry from Hyannis to Oak Bluffs on the boutique island of Martha's Vineyard. Hire bicycles and ride to the south shore for the beautiful beaches.

    • Top Tip 5

      So much of New England is about food! Try clam chowder in famous Quincy Market Food Hall, fresh lobster anywhere in Maine and, of course, a tub of Ben & Jerry’s ice cream made in Vermont.

    • Top Tip 6

      Visit the Berkshires, Massachusetts in summer time and catch one of the many summer festivals. It’s the summer home of the Boston Symphony Orchestra, the theatre festival in Stockbridge and the music festival in Tanglewood.

    • Top Tip 6

      Ride the Cog Railway to the peak of Mount Washington in New Hampshire. You'll travel above the clouds and see some spectacular scenery along the way.

    • Top Tip 8

      Old Sturbridge Village, Massachusetts is a living history museum which recreates an 1830’s New England rural village. Costumed staff perform the routines of everyday life of the 19th century.

    • Top Tip 9

      Visit the breathtaking millionaires’ mansions of Newport, Rhode Island, built over 100 years ago by America's wealthiest families - the Vanderbilt’s, Astor’s and Belmont’s to name but a few.

    • Top Tip 10

      Enjoy a summer boat ride aboard The Spirit of Ethan Allen or a lunch cruise on the Northern Lights cruise ship on the 125-mile long Lake Champlain.

    You may also be interested in...
  • The Best of New England

    Begins in and ends in Boston, Massachusetts

    15 Days / 14 Nights

    Departures: year round

    Add this Fly Drive to planner

    Your fly drive includes

    • Round trip scheduled flights
    • Intermediate 4 door car hire, including insurances and satellite navigation.
    • Accommodations as stated
    • Personalised Road Book
    • Coastal Maine


    • Pretty Lighthouses


    • Fall Colours


    • Boston


    • Kennebunkport


    • Bretton Woods


    • Vermont Church


    • Bar Harbor



    Arrive Boston

    Depart the UK on your chosen scheduled flight to Boston. Upon arrival proceed to your hotel, the Fairmont Copley Plaza, an iconic hotel in a location central to many attractions.

    Hotel: Fairmont Copley Plaza



    The cosmopolitan city of Boston is a delight to visit. Great food, wonderful shopping and a wide array of attractions will keep you entertained. Explore the Freedom Trail, shop at Quincy Market or try a Boston 'Duck Tour' and get to see the city from land and water.

    Hotel: Fairmont Copley Plaza




    After collecting your rental car, this mornings drive takes you north into the coastal state of Maine. En route, visit Salem, known best as the home of witchcraft. Your drive takes you along the beautiful Massachusetts and Maine coastlines, scattered with small towns and villages to the pretty town of Kennebunkport.

    Hotel: White Barn Inn



    The White Mountains

    We suggest you take time today to journey further along the Maine coastline before heading inland and perhaps stopping in North Conway for fabulous outlet shopping or to travel the North Conway Railroad. Explore the White Mountain National Forest and take the Mount Washington toll road to the summit of New Hampshire's highest mountain. On your second day, why not make the journey south to Meredith? Perched on Lake Winnipesaukee, Meredith has an idyllic setting and a warm personality.

    Hotel: Omni Mount Washington Resort



    Stowe & The Green Mountains

    Crossing the state line into Vermont today takes you into Green Mountain country. No matter what time of year you visit there's a lot to keep you entertained, from hiking and skiing to browsing the quaint village shops.

    Hotel: Green Mountain Inn



    Lenox & The Berkshires

    Today visit Shelbourne Museum's collection of Americana, scenic gardens and the side-wheeler SS Ticonderoga. Perhaps take a detour to Woodstock, a quintessential New England village with traditional shops and covered bridges. Tonight, you'll stay in the beautiful Berkshire in a town which is the summer home of the Boston Symphony Orchestra.

    Hotel: Cranwell Resort, Spa & Golf Club




    This morning visit the Francine Clarke Art Institute or the Hancock Shaker Village, a restored 19th century settlement before journeying south into Connecticut. As a result of its close proximity to New York City, Connecticut assumes some of the Big Apple cosmopolitan chic whilst retaining its distinctive New England character.

    Hotel: The Mayflower Grace




    Enjoy a relaxing morning in Washington, Connecticut before continuing your journey into New England's smallest state Rhode Island. Newport was the summer resort of the first millionaires. Spend a day by the beach or tour the Cliff Walk and Ten Mile Drive with its extravagant mansions.

    Hotel: Vanderbilt Grace



    Cape Cod

    Journeying east today you leave Rhode Island and return once again into Massachusetts, and on to ever popular Cape Cod. We've allowed three nights so you get the opportunity to explore this wonderful area. Take a trip to Provincetown and enjoy a whale-watching cruise, take a ferry across to Martha's Vineyard or Nantucket Islands and a day strolling the historic town of Chatham.

    Hotel: Chatham Bars Inn



    Chatham Bars Inn

    Make the final journey back to Boston Airport. En route, visit Sandwich and Plimoth Plantation, a living museum depicting life in 1627. Return your car and check-in for your flight to the UK.


    From £3625 per person based on twin occupancy of Standard rooms in low season. Other prices available on request.

    You may also be interested in...