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Family Reunions on Cape Cod, Nantucket & Martha's Vineyard

The Cape and Islands is the ideal spot for your next family reunion. With so many beaches, restaurants, activities, and sightseeing opportunities, everyone is guaranteed to have a good time. A large vacation rental home offers plenty of bedrooms for privacy but also offers spacious living areas where everyone can gather for family games, talks, and dining. By staying in a home, you have access to your own private outdoor spaces where kids can run and adults can lounge. And you have the ability to prepare your own meals if you wish. In terms of cost, it is generally much more cost effective to rent a home with many bedrooms than pay for many hotel rooms. So when planning a family reunion, consider a vacation rental home on the Cape Cod, Nantucket or Martha’s Vineyard.

Family at Jackknife Beach in Chatham
Jackknife Beach in Chatham

When to go: Summer is a popular time as the weather is ideal for beach going and outdoor activities, but the shoulder seasons of spring and fall offer a great time to visit, too. There are still beach days but no summer crowds, rental rates tend to be lower than during the summer season, and homeowners are more willing to rent for shorter periods of time

Where to stay: Once a consensus has been reached regarding the time of year to hold the reunion, it is time to start looking for your home away from home. has a variety of homes that can meet the needs of most parties, from those that are suited to smaller groups to homes that can accommodate over 25 guests. A rental home provides you with space to gather, and space to spread out.

Staying in a home with lots of history while you explore your own family history during your reunion can be inspiring. Our Great Gatsby (ID #4612) in Chatham was built in the 1930’s by good friends of F. Scott and Zelda Fitzgerald.

With the gorgeous weather in the summer and fall, you will not be spending much time inside, so be sure to find a vacation rental with plenty of outdoor space! ID #4564 has an amazing view of Oyster Pond with access to the water for kayaking and paddleboarding — perfect for spending time with the whole family during a reunion. And if you’re looking for proximity to gorgeous Mayflower Beach in Dennis, look no further than ID #29298. Or, if you’re considering the Vineyard, take a peek at ID #26587 in Oak Bluffs, featuring water views and a dip pool!

Want to be within walking distance of a town so that you can stroll to shops and restaurants? This luxurious estate on Nantucket (ID #4804) affords plenty of privacy, yet is a five-minute walk to Main Street.

Yarmouth Vacation Rental for Family Reunions
Yarmouth Vacation Rental - ID 2602

What could be more fun than for your family to have access to their own private pool? Not only does this lovely home in Eastham (ID #29796) have a pool, but it’s located close to Cook’s Brook Beach. If you enjoy spending time with your extended family but also need some space, then consider a vacation rental with an estate feel. This large home at the mouth of the Bass River in Yarmouth (ID #2602) can give you just that. With 7 bedrooms, private beach, and an extra large living area there is plenty of space to enjoy time both with, and away from, your family. Another great option with a pool, (ID #23584), has 6 bedrooms and is located within a close distance of the popular Sandwich Boardwalk.

Lots of brothers, sisters, aunts, uncles, nephews, and cousins? Then an extra large vacation home is a must, and with 6 bedrooms and a guest house. (ID #35307) in Falmouth can most certainly meet the needs of a large family reunion.

Want to stay together but still have some privacy for individual families? Consider this oceanfront home with two guest cottages on a private beach in Dennis Port (ID #4640).

And if you’re looking for a more unique experience, consider ID #35227 in Sandwich—a transformed historic landmark, a church!

Planning your meals: With access to a fully equipped kitchen in your vacation rental, meal preparation can be done with ease and at considerably less cost than eating out. You may want to assign a few different members to be responsible for dinner for the group each night. Other dining options include planning an evening out, and the Cape and Islands are filled with a wide variety of wonderful restaurants that can accommodate large groups. Or, better yet, stay in with your family without taking time to prepare a meal! Hire a catered clambake or have a chef come into the home and cook for the group. That way, you can enjoy spending time with your family in a relaxed environment and leave the cooking to someone else! Here's a 7 bedroom New Seabury home (ID #16151) with an immaculate kitchen. And, it's close to the beach!

Planning activities: A great benefit to staying in a vacation rental is having access to a yard that can allow you to organize such fun, family-friendly events. One popular family reunion activity is arranging an old-fashioned field day that includes such fun family games as an egg and spoon race, water balloon toss, three legged races, or a tug-of-war. Additionally, you can arrange for beach days, museum days, or go deep sea fishing or on a golf outing (mini or 18 holes), sightsee on your own, or arrange for tours. Whale watches are another great way to spend a day, and there is no doubt that seeing a whale up close is an unforgettable experience. Also, don’t forget about the extensive bike trails, hiking trails and walking trails offered throughout the Cape and Islands. Find things to do on Cape Cod.

Providing welcome gifts and keepsakes: Consider providing a “goody bag" to your family members upon their arrival. The options for this are endless and can be as simple or extravagant as you choose. Perhaps a beach bucket filled with local goodies (think Cape Cod Potato Chips or Nantucket Nectars), a personalized t-shirt, or water bottles. Many gift shops on the Cape and Islands can help you create the perfect welcome gift.

Capturing the experience: You will certainly want to have your reunion documented for future enjoyment, and to share with others. What better way than through photographs? In addition to snapping your own photos, consider hiring a professional photographer. A group photo taken on the grounds of your vacation rental or at one of the beautiful area beaches will provide a wonderful memento of your special family reunion.

Use the Power Search to find the perfect Cape Cod vacation rental for your next family gathering.

About Elizabeth Weedon

About Elizabeth Weedon: I have worked for since 2008, and I've been a loyal homeowner listed on the site since early 1998. An enthusiastic member of the Homeowner Support Team, I provide fellow Cape and Islands vacation rental homeowners with advice about online marketing and rental management techniques to ensure them a successful rental experience each season. In addition to phone and email support to our homeowners, I also create and edit much of the content on our website, as well as our Homeowner Blog and monthly newsletters. I am also the Press & PR Coordinator for the company, responsible for drafting our press releases and responding to press inquiries and interviews. I grew up summering on the Vineyard, where I have managed my family's rental home since the mid-1980's, and I'm passionately devoted to the Island. My husband and I live in Wellesley where we have raised our 2 grown kids and our Black Lab, Maisie.