6 Br Private Vacation Home Vacation Rental In East Dennis, Massachusetts

Welcome to your dream getaway at 58 Pleasant Street in East Dennis, where luxury meets comfort in this fully renovated, oversized home. Nestled in a serene setting, this exquisite property combines thoughtful finishes, artful design, and spectacular amenities, making it the perfect choice for the most discerning renters.

As you step onto the meticulously landscaped grounds, you'll find a grand main home, a charming guest house, and a heated saltwater pool and spa. The main home greets you with an expansive living space, featuring a gourmet kitchen equipped with top-of-the-line appliances, a cozy breakfast nook, and an inviting sitting area. Perfect for entertaining, the dining room comfortably seats 14 and is conveniently located near the kitchen. The main level also boasts a library/office room, offering a quiet retreat near the front door, and a cozy den off the main living area, ideal for intimate conversations or spirited board games. A side entrance leads to a mudroom and a full bathroom, adding to the home's thoughtful layout.

Upstairs, the home offers four beautifully appointed bedrooms, including two with ensuite baths. The primary bedroom features a spacious deck overlooking the pool area and guest house, providing a tranquil space to enjoy your morning coffee or evening sunset. The lower level of the home includes a finished rec room and an additional bedroom, offering even more space for relaxation and entertainment.

The guest house is a delightful retreat on its own, complete with a well-equipped kitchenette, a comfortable living area, and a full bath. Combined, the main home and guest house comfortably accommodate up to 14 guests, making it ideal for large families or groups of friends.

Location is key, and this property does not disappoint. Cold Storage Beach is just 0.6 miles away, offering pristine sands and sparkling waters for your enjoyment. Dennis Village, located 3 miles away on historic Route 6A, provides charming shops, delightful eateries, and a glimpse into the area's rich history.
Experience the perfect blend of luxury and convenience at this exceptional Pleasant Street property, where every detail has been thoughtfully designed to create an unforgettable vacation experience. Whether you're lounging by the heated saltwater pool, enjoying a meal in the elegant dining room, or exploring the local attractions, this home promises to be your ideal home away from home.

The home is available for year round bookings. Please see below for minimum stay requirements based on the time of year. Please note, off season bookings do not include the pool, spa or guest house and occupancy for these bookings is capped at 12 people in the main house only. The cleaning fee is reduced as well during these stays.

Subject to applicable taxes and fees. No pets please. All linens and towels are provided. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver insurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional security protection which may be required at this property.

STAY REQUIREMENTS:
8/30/25- 10/3/25- 4 night minimum stays (Pool and Spa are Open)
10/4/25 - 5/15/26 - 3 night minimum stays (Pool and Spa are Closed)
5/16/26 - 6/26/26 - 4 night minimum stays (Pool and Spa are Open)
6/27/26 - 8/28/26 - 7 night minimum stays, Sat. to Sat. only (Pool and Spa are Open)
8/29/26 - 10/2/26- 4 night minimum stays (Pool and Spa are Open)
10/3/26 - 12/31/26 - 3 night minimum stays (Pool and Spa are Closed)

BEDROOM CONFIGURATION:
Main House 2nd Floor:
Bedroom 1 (Primary Suite)- 1 king bed w/ ensuite bathroom
Bedroom 2- 1 queen bed w/ ensuite bathroom
Bedroom 3- 1 queen bed
Bedroom 4- 2 double beds (1 double w/ double trundle bed underneath)
Main House Lower Level:
Bedroom 5- 4 single beds (2 sets of trundle day beds)
Guest House 2nd Floor:
Bedroom 6- 1 king bed

Located in South Dennis, this vacation home is near the beach. The area's natural beauty can be seen at Cape Cod Beaches and Mayflower Beach, while West Dennis Beach and Cape Cod Inflatable Park are popular area attractions. Cape Codder Water Park and Cape Cod Museum of Natural History are also worth visiting. Discover the area's water adventures with sailing and fishing nearby, or enjoy the great outdoors with hiking and cycling.