Eastham is a lanky piece of land bordered by Cape Cod Bay and the Atlantic Ocean – it seems everywhere you go, there’s beach. The so-called "Gateway to the Cape Cod National Seashore" is, well, just that. For an easygoing intro into Massachusetts’ carefree coast, choose Eastham summer rentals. We’re not just here to shelter you during your stay, though. We’re here to help you plan for it! Scroll down for our in-depth Eastham Travel Guide, and if you have tips for how we can improve it, please share.

What to Do In Eastham, Massachusetts

Eastham is one of Cape Cod’s most lackadaisical towns, and that’s the way everyone likes it. Besides stumbling on to a few nuggets of the area’s vibrant colonial history, you’ll spend your time eating, drinking, swimming, and sleeping here. Turn off your blackberry, mentally check out of work (not just physically!), and enjoy your supine Eastham existence while it lasts.

Top Eastham Attractions and Activities

  • Eastham BeachThe Beach – The waves of the Atlantic Ocean are rough and tough, while the bays are calm and kid-friendly. Popular beaches include Great Pond, Coast Guard Beach, and Nauset Light Beach. With Eastham beach house rentals, you’ll never be far from the shoreline.
  • Play tennis on any of Eastham’s several public courts.
  • Jazz things up with a bike, kayak, or canoe ride – seeing the sights on foot gets stale.
  • Go freshwater fishing on Minister Pond or Herring Pond. Not into that? Try shell fishing instead.
  • Stroll through Fort Hill and make sure to stop to smell the fresh ocean air, gaze at interesting birds, and absorb the tranquility of Eastham’s unique marshland.
  • The 1869 Schoolhouse Museum – The local museums don’t pack too much punch, but Eastham’s got a few surprises up its sleeves, like this one. Go back in time for a little while and study Native American artifacts and other relics from the town’s past at this restored school. Admission is free!
  • Salt Pond Visitor Center – Learn about what makes the Cape Cod National Seashore so special via the educational and insightful exhibits on display here. Just outside the center are a group of very walkable trails.
  • First Encounter Coffee House – This former church is now the number one hangout spot in Eastham, especially on the occasional Saturday night when a folk, bluegrass, jazz, or rock musician will take the stage. Got children? They get in free.
  • Captain Penniman House – Is this a maritime/whaling musuem or historic estate? Well, it’s both, and that's why it's well worth a tour.
  • Wiley’s Gym, Fitness and Wellness Center – If you're feeling restless, head here for a Pilates class or rock climbing session, and then cap it all off with a massage.

An Eastham beach home is the perfect companion to your Cape Cod getaway, but it’s okay to get out of town for a night on the town. Chatham, Brewster, Wellfleet, Provincetown, and other more “metro” Massachusetts cities are all near by.

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What to See in Eastham

Even though there’s little to do in Eastham, there’s a lot to see – other than the breathtaking, ocean-framed sunset, that is.

  • Eastham Windmill – It wasn’t really built in the 1680s, but its aged appearance is intentional, meant to remind passersby of Eastham’s past.  
  • Old Cove Burying Ground – This cemetery in the forest is three centuries old! We’ll leave it up to you to determine if a visit here is “morbid” or “historic.”
  • What will the tide bring in today? Eastham’s tide recedes two times a day and that means you’ll have plenty of opportunity to see fascinating marine life, like horseshoe crabs, wash up on the shore.
  • Nauset Lighthouse – This restored beacon is now Eastham’s preeminent landmark.

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Where to Shop and Eat in Eastham

It’s funny how hungry a nap on the beach can make you. Eastham has lots of dining options for you to wake up to.

  • Eastham Seafood RestaurantsArnold Lobster’s Clam Bar – The food here is fast, fresh, and ready-to-go. Take a pound and a half of steamed lobster or basket of fried clams home or chow down at the restaurant’s outdoor patio. Is it really “the best clam shack on Cape Cod?” You decide.
  • Ben & Jerry’s Scoop Shop – Take a cool break from the Cape Cod sun with a smoothie or a cone overflowing with ice cream.
  • Eastham Lobster Pool – Gather for a good old clambake at this seafood mainstay.
  • Jimmy D’s Restaurant – It’s the sports bar of all sports bars. You can even watch golf here. In between joking with the bartender and yelling at the game, make sure to order some food and drink.
  • Beach Break Grill and Lounge – Chill out at this surfer-themed dive.
  • Friendly Fisherman’s – If you like lobster rolls, you’ll love this top takeout spot. 
  • Fairway Restaurant & Pizzeria – For breakfast, try the Crab Cake Benedict or potato pancakes. For dinner, you can’t lose with a calzone or simple slice of pizza. 
  • Red Barn Pizza – For food with some fun on the side, head here. Mini golf and an arcade all accompany the appetizing menu of pizza, subs, and salads.
  • Sam’s Deli – Some days you just feel like a sandwich. And for those days, this deli is a sandwich oasis in a desert of seafood and pizza joints.

Shopping’s an integral part of many vacations, even if you stay on the outside of every shop window. Eastham’s got a nice sampling of gift and specialty shops for you to peruse.

  • Fly Shop Closeouts – Here you can buy fly fishing bait and tackle.
  • Collector’s World – If you’re looking for a souvenir that’s not a keychain or magnet, this antiques shop is the place to go. 
  • Kitson Fine Arts – What does the ocean surrounding Eastham look like through an artist’s eyes? Find out here. 

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When to Visit Eastham

If Eastham’s a little too soporific for you, forgo the classic Eastham summer rentals for a September vacation, so you can take part in the busy Eastham Windmill Weekend, featuring clam chowder cook-offs, raffle prizes, kids activities, square dancing, and live music.

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Getting to Eastham, Massachusetts

You have two choices for airports when traveling to Eastham. Hyannis’ Barnstable Municipal Airport is just 30 minutes from Eastham, while the Logan International Airport in Boston is an hour and 47 minutes away. No matter what airport you land in, though, you won’t have to spend much time in a car.

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Why Eastham Vacation Rentals?

When planning your Cape Cod vacation, seriously consider Eastham summer rentals. No matter what you plan to do or where you plan to go during your trip, there’s nothing quite like a comfy, spacious Eastham condo or home rental to crash in every night. And with all the money you’ll save on Eastham beach rentals vs hotels, you’ll really be able to relax and give in to the town’s leisurely pace.

So, whether you plan to explore everything that exists South to North Eastham, or you’re just hoping to fish all day every day on Minister’s Pond, Eastham vacation rentals make a great foundation for your vacation.

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