A Cape Cod vacation has long been a part of the American dream, offering beach days, lobster dinners, and a stroll through our nation’s past, but did you also know it could be a vacation filled with lazy pool days as well? We at Pretty Picky Properties are proud to offer vacation rentals that even the most discerning of traveler’s flock to, offering luxury amenities, including private pools, to enhance your vacation experience. Today, we would like to take you on a tour of our Chatham, MA vacation rentals with pool, perhaps helping to narrow down your rental choice to just one that will become an integral part of your vacation experience!
Testimonials | FAQs
Chatham, Massachusetts Vacation Rentals for Most Sizes of Traveling Groups
Chatham is a town located in the elbow of Cape Cod, known for its beautiful Main Street filled with charming shops, the still active historic Chatham Light, and for being home to a large number of our Pretty Picky Properties vacation retreats, many of which offer private pools for your enjoyment. These spaces range in size from spacious 3-bedroom retreats to generously sized 8-bedroom sanctuaries, ensuring that no matter how many people are in your traveling party, you will find a property that fits your group like a fine leather glove. Luxurious, stylish, and welcoming to all, their private pools are often heated, enabling guests to swim comfortably during their stay, but the pool is just the start of the long list of amenities guests will find on the other side of the entrance doors!
Filled with Light
The Cape Cod landscape is sure to take your breath away and we want to make sure that you get all the opportunities to enjoy it, so our Chatham, Massachusetts vacation rentals with pools will also feature a large number of generously sized windows, ensuring that the homes stay light, even on rainy days. Stepping inside for the first time, the Pretty Picky Properties difference will immediately be apparent, both in the vibe (casual, yet upscale, and always welcoming!) and in the furnishings, appliances, and electronics that are housed within.
Follow the paths created by floors often constructed from wood into rooms where the luxuries will make you feel spoiled and the ambiance will make you feel relaxed, starting with our living rooms. New England homes aren’t often known for their open concept floor plans, but the majority of our Chatham retreats will offer this style of floor plan, ensuring that even as you lounge on slipcovered sofas, idly scrolling through the guide on the state of the art television, you can stay connected with your family members hanging out in the other public spaces, enabling you to stay close.
Testimonials
Paul N.
Our second time at Whale Song in Chatham and all was great.
Elizabeth S.
We loved our stay. Location, cleanliness and ease of communication was all great. They even accommodated a last minute early check in as we had an event to get to. Thanks!
Alison C.
Thank you so much for a beautiful Chatham stay. We loved making new Cape memories here. The house is super fun for families with the pool and backyard as particular highlights.
Outdoor Amenities Enhance Your Vacation Experience
If there is any greater way to honor a warm and sunny summer day than by hanging out poolside, sipping margaritas and watching the kiddos splash in clear waters, please tell us! And because relaxation is key during your Cape Cod getaway, our outside areas will include even more ways to relax and be spoiled. Firepits are popular after the sun sets, leading to marshmallow roasts and scary stories, and parents, after a long day of strolling through the Sylvan Gardens or exploring the Monomoy National Wildlife Refuge, the restorative benefits of soaking in a hot tub with the jets hitting every aching spot, are priceless.
Lounge chairs padded with thick cushions somehow make your tropical drinks taste even better, and because a good old-fashioned family barbecue is a popular summer tradition, gas grills and outdoor patio furniture will enable you to stay outside even longer! Cornhole games, hammocks, and outdoor showers are more amenities you might find in the large backyards of our Chatham, MA vacation rentals with pools.
A List of All the Luxury Extras
When you come inside, however, it doesn’t mean the fun times or the spoiling moments will come to an end, especially as we are known for offering luxury extras that we don’t charge extra for! Some of these spaces may offer fully equipped game rooms featuring game tables, arcade games, and even video game consoles, or your space may just be equipped with a pool, ping pong, or foosball table, still offering more ways to play.
Didn’t plan ahead? Check out our last-minute Chatham house rentals available and seize the moment!
Gas fireplaces in living rooms and bedrooms will add romance and warmth to your visit, coffee bars and wet bars will ensure that your hydration needs are met, and if your retreat doesn’t offer a private home theater, super-sized televisions mounted across from soft and plush sofas or sectionals will give guests a similar experience. Gourmet kitchens, quiet sitting areas, and deep soaking tubs in spacious and spa-like bathrooms will ensure that this vacation will top all others that you have taken.
Reserve your favorite Chatham vacation rentals here today!
FAQs about our Chatham, MA Vacation Rentals with Pool
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Do any of your vacation rentals with pools offer water views as well?
Although it is rare to find homes with both a pool and water views, some of our most popular Chatham retreats do offer both, including one memorable property that sits on the shores of Frost Fish Creek and provides its own private dock.
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I like to golf, does Chatham offer any courses?
Chatham Seaside Links, located at 209 Seaview Street in Chatham, is a charming 9-hole course that was established in 1895, adding a historical flavor to your game.
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We are traveling with our teenage children and would prefer not to have to watch the same television shows as they do. Do your properties offer multiple living areas?
Yes, many of our properties offer more than one living area. The separation between parents and teens can be a life saver, enabling teens to claim one living space as their own while parents can claim the other.
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We love seafood, do you have any recommendations for restaurants in Chatham that are casual and child-friendly?
Chatham Pier Fish Market, 45 Barcliff Ave #2, will more than likely become your favorite place to eat, offering delicious and fresh seafood as well as an observation deck that is perfect for watching boats, dolphins, and friendly seals that like to hang out in the area.
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Are any of your properties with pools also pet-friendly?
Yes, Pretty Picky Properties offers vacation rentals in Chatham that offer pools and are pet-friendly ensuring that your entire family can enjoy a once in a lifetime Cape Cod vacation.