New England Vacation Rentals Ultimate Guide to 7 Days in Cape Cod in the Summer

As summer draws ever closer, it is time to start making plans for the annual seasonal vacation, the one week out of your year where your only responsibilities are to see something new and have an amazing time while you do it. These seven days of freedom give you the time you need to recharge, refresh, and renew, and it just so happens those seven days can be especially exciting and relaxing when you choose New England Vacation Rentals for your vacation escape. Summer on Cape Cod is the most wonderful time of the year, and from mid-June until Labor Day, our vacation rentals become available for Friday to Friday seven-day bookings. This is the only way to book from us during the busiest season of the year, but there is no hardship in using your precious vacation days on Cape Cod, especially when you follow our guide to seven amazing days on our historic Cape!

Day 1: The Fun Starts NOW!

Your first day on Cape Cod is one generally spent stocking your kitchen, choosing your bedroom retreat, and getting a feel for the area you have chosen to make your home away from home for the next seven days of your life. Choosing your bedroom is easy, and whether you are the type of traveler who prefers to live out of their suitcase or one that has to unpack and put everything neatly away, (there will be plenty of storage and closet space in your Cape Cod sanctuary) a quick trip to the Chatham Village Market or the local Shaw’s grocery store will free you up to start exploring!

A sunset walk should be added to your daily itinerary, for there is no better way to enjoy the beaches of Cape Cod than by witnessing the fiery colors that light up the sky each evening. But for now, even as the day is nearing its natural conclusion, it is time to gather up the family and grab something to eat, and although your fully equipped kitchen is newly stocked with everything you need to create a full meal, we suggest that a dinner at the Impudent Oyster, 15 Chatham Bars Avenue, is the best way to finish off your first day in paradise! This is a popular spot, serving the tastiest seafood on Cape Cod, so reservations are suggested for dinner and can be made by calling 508-945-3545. They also serve land mammal dishes, and if you are looking for a taste of something fancy, their Duck Wesley is the perfect dish to sample!

Day 2: Which Way to the Beach?

On your first day on Cape Cod, you may have already enjoyed a taste of the beach with a sunset stroll, but today is all about staking your claim on a stretch of sandy beach and experiencing all that an ocean by the sea has to offer! There will be plenty of time to explore local attractions on days three through seven, but on day two, sunny skies and the roaring ocean are calling your name.

Depending on which of our properties you are staying in, you have a varied selection of beaches on which you can play, but if you get the chance, try to spend at least one day at Mayflower Beach in Dennis. This popular beach offers three parking lots, so if you are staying in other villages, you should be able to find a parking spot for your rental car. The water is a touch warmer on this shore and the waves crest high, ensuring that the surfers love this spot as much as you will, as it gives you something to watch during your lazy moments on the sand! At lunch, Chapin’s, located just steps away from your umbrellas and beach chairs, is the perfect spot to enjoy all your favorite seafood dishes and vacation cocktails; their Patio Painkiller made with Rumhaven Coconut Water Rum, New Amsterdam Mango Vodka, pineapple juice, and a dash of nutmeg is dangerously delicious!

Day 3: A Tour of Lighthouses

The lighthouses of Cape Cod have guided many a sailor to safety, but they are also popular with tourists who have not grown up by the sea, so why not take a self-guided tour to see what all the fuss is about! You may have already posed for the family Christmas card in front of Chatham Lighthouse, but there are many more to explore and love.

The Three Sisters Lighthouses, located on Cable Road in Eastham, were moved to their current location when erosion at the shoreline could have caused them to be lost forever. (The original Three Sisters were built of brick and did end up falling into the sea; this version is wood built on stone foundations.) Nauset Light, also located in Eastham, may look familiar to you, as it is the star attraction on bags of Cape Cod Potato Chips! Stage Harbor Light in Chatham—located on private property, but easily viewed from Harding’s Beach in Chatham—and West Dennis Light (formerly known as Bass River Lighthouse) are just a couple more examples of lighthouses you should be looking out for during your unforgettable stay on Cape Cod. You may not get to see the inside of some or any of these beautiful structures, but we can promise that the pictures you will take will all be frame worthy, enticing you to hang them on your walls in a place of honor!

When it comes time for dinner, a special day spent touring the lighthouses deserves the incredible meals found at The Brewster Fish House at 2208 Main Street. Even though your tour of lighthouses did not bring you to Brewster, it is worth driving a few more miles to taste the seafood offered here, starting with their creamy and delicious lobster bisque!

Day 4: The Perfect Day

As you reach the midway point of your Cape Cod getaway, you have started to settle in and are realizing that you really have stepped out of your real life right into paradise, and that makes day four the perfect time to enjoy the perfect day on Cape Cod. Early risers can start this day out with a walk along the shores nearest your New England Vacation Rentals getaway, watching the sun rise over the sea and marveling over the many colors displayed in the sky. After, you can always head back to your sanctuary for a little more sleep, or you can mosey on over to the Hole in One Breakfast & Lunch, 98 MA-6A in Orleans, for a breakfast you will never forget. This is where the locals go for hearty breakfasts and sweet treats that you will miss when you return home to real life—especially their donuts!

While you are in Orleans, stop by the Jonathan Young Windmill Collection at 41 Old King’s Highway for a sneak peak into the history of the Cape and some really cool pictures of a windmill that was constructed in the 1700s. Lunch at the Oyster Company (202 Depot Street in Dennis Port) breaks up the long day in the most delicious of ways, and after, one last touristy stop at Cranberry Bog Tours, 1601 Factory Road in Harwich, is where you will discover those commercials for cranberry juice weren’t exaggerating about what a cranberry bog looks like. By now you are probably pretty hungry, so we will finish up the day with a few hours of relaxation at your favorite beach, watch the sun set over the sea, and head back to your vacation home away from home for a home-cooked dinner enjoyed on the patio!

Day 5: A Step into the Past

From your first moments on Cape Cod, you cannot help but be wowed by the history that surrounds your every step, and as such, a day spent steeped in history will be a memorable one. From a sea captain’s home clad in stereotypical clapboard siding offering widow’s walks and the scents and sounds of the sea to the museums that highlight the beauty of the Cape by exploring its history in depth, this beautiful place is rich in history and charm, and after devouring a delicious and filling breakfast at Grumpy’s, 1408 Main Street Route 6A in East Dennis, it will be time to explore some of the museums and historic sites that have made Cape Cod famous.

The Edward Gorey House, also known as the Elephant House, is where the famous author, illustrator, and playwright finished out the later years of his life. Located at 8 Strawberry Lane in Yarmouth Port, today his home serves as a museum for his work and a celebration of his life. Get a glimpse of what life was really like for Cape residents in the early 1800s with a visit to the Caleb Nickerson Homestead, located at 1107 N Orleans Road in North Chatham, marking the grounds where the first settlers set up residency in 1664. Tours are available on Wednesdays only in the summer months, which conveniently happens to be day five of your Cape Cod getaway! Chatham played its part in the last World War, with local lads sacrificing their lives, including one private who was killed during the attack on Pearl Harbor. Boat builders contributed designs for boats and local women set up a Civilian’s Defense Committee and knitted warm sweaters for their boys at war. The Chatham Historical Society, based in the Atwood Museum, 347 Stage Harbor Road, tells these stories and so many more in your final historical stop of the day. Spend a few hours exploring the renovated captain’s house built in 1752, and marvel at how much has changed on Cape Cod over the centuries and how much has stayed the same!

Day 6: How Has Time Passed So Quickly?

Why is it that the months leading up to vacations seem to stretch out in an endless array of seconds, minutes, hours, and days, but your seven days on Cape Cod fly by in a blink? On your last full day on the Cape, there are still so many things you want to do and seemingly so little time in which to do it! After five days, you have experienced much of what Cape Cod has to offer, so this day is dedicated to shopping and more time at the beach, starting (and perhaps ending!) with the shops on Main Street in Chatham. Grab a few gifts for yourself and the family members or friends back home who were not fortunate enough to join you on this getaway at Yankee Ingenuity, a gift shop found at 525 Main. Savor the enchanting souvenirs found at Mermaids on Main (410 Main), including whimsical gifts which are interspersed with vintage items that you never knew you needed! The Tibetan Gift Shop (595 Main) features wares with an Eastern and mythical flair, and the Mayflower shop (475 Main) offers a little of this, a little of that, and a lot of everything in this historic shop that has decorated the Chatham landscape since 1875! One shop that you will want to leave Main Street for is the Chatham Jam & Jelly Shop, located at 16 Seaquanset Road. Offering sweet treats that will serve as a fleeting reminder of the sweet memories made on Cape Cod, everything made here is created with local produce, ensuring that the sweetness is fresh as well!

Day 7: The Memories Will Last Forever

No one wants the good times to end, but your Friday to Friday seven-day booking in our New England Vacation Rentals summer sanctuaries has come to its natural conclusion. Before you check out and begin your re-entry to real life, there is still time for one more trip to the beach, one last seafood meal, and one final look back at the sturdy Cape Cod home that sheltered you and provided relaxation over the last week. The living room where you enjoyed a roaring fire on cooler nights, the fully equipped kitchens in which many meals were created and stories were shared, even the dining room table where you and your family gathered around playing games and devouring foods, talking loudly and laughing even louder. These memories will be ones that will be treasured forever, and as you pack your bags (Aren’t you glad you brought that collapsible bag found on Amazon that is now filled with all the goodies you purchased over the course of your Cape Cod adventures?) and walk away with your luggage trailing behind, you may not even recognize how relaxed, happy, and renewed you feel. Reserve your favorite summer sanctuary today!