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Experience the charm of Marblehead, Massachusetts at Sailors Aweigh, a spacious 3-bedroom, 1-bathroom vacation home with a stunning outdoor space. This cozy retreat features an amazing backyard with a large deck, BBQ, and expansive lawn perfect for relaxing or playing croquet. Inside, you'll find a well-equipped kitchen with full-sized appliances, a cozy sunroom with a large smart TV, and a living room with a decorative fireplace - ideal for conversation or quiet relaxation. The home comfortably sleeps up to 6 guests across 3 queen-sized bedrooms. Situated in the historic town of Marblehead, Sailors Aweigh puts you just steps from the beach, restaurants, pubs, and shops. Explore the charming, narrow streets lined with 18th-century homes, marvel at the breathtaking harbor views, or enjoy a day at the nearby Devereux or King's Beach. This quintessential New England escape offers the perfect blend of comfort and adventure.
This description is for informational purposes. Please verify all details, including amenities, policies, fees, and availability, on the booking platform before booking.
You’ll be staying in someone’s home, so please treat it with care and respect.
House Rules: Good Neighbor and Respectful Visitor Welcome! We hope you will stay with iTrip North Shore. We would be delighted to be host your visit! iTrip North Shore strives to provide excellent service and assistance.
Guests are expected to honor our House Rules to be Good Neighbors and Respectful Visitors.
Good Neighbors honor the right of Sailors Aweigh’s neighbors to peacefully enjoy their homes. iTrip North Shore's guests will:
Respect Quiet Hours: Quiet Hours are dictated by local rules and ordinances. Unless specified otherwise, quiet hours are between 10PM and 8AM.
Not Host Events or Parties: without express written approval from iTrip North Shore, do not host any parties or events.
Follow the Law: do not do anything illegal.
Respect Boundaries: Do not encroach into the neighbors’ space, including but not limited to yards, gardens, decks, patios, and parking spaces. Do not use neighbors’ amenities or take neighbor’s property, such as: furniture, grills, pools, spas, etc.
Follow Parking Instructions: Please follow all parking instructions and only use those spaces allotted to Sailors Aweigh.
Respectful Visitors: remember you are renting a private home; iTrip North Shore guests will treat Sailors Aweigh with the same or more respect that they would like shown to their belongings:
Prudent Use: instructions on how to use appliances and amenities are provided. Please use all items for their intended purpose and per instructions. Please contact iTrip Vacations North Shore Massachusetts if you have any questions.
Be Neat and Caring: please do pick up after yourselves; put trash and recycling in proper bins, do the dishes, use coasters, and leave the furniture where it belongs.
Park in Designated Areas: Please do park in driveways, parking pads and garages. Please do not park on lawns or in gardens.
Do Not Smoke or Vape: smoking or vaping of anything: cigarettes, pipes, cigars, or marijuana, requires special remediation to remove the aroma.
Do Not Tamper with Safety Sensors: iTrip North Shore homes come equipped with a variety of safety sensors, such as: exterior cameras, noise monitoring, smoke detectors, carbon monoxide detectors, and more. Respectful guests do not tamper with the owner's safety sensors.
Be Careful: where there are wet area amenities such as waterfronts, docks, pools, or hot tubs, please take care to secure the areas and take appropriate precautions.
Return Keys/Passes/Remotes: please return items as described in Check-out instructions.
Please know that violating House Rules is grounds for terminating our agreement.
Please enjoy this lovely home with respect for the home and the neighborhood.
Enjoy your stay!
About WiFi Sailors Aweigh provides high-speed internet services. Internet services have been shown to meet the needs of guests traveling for both work and pleasure.
Minimum Age Minimum age for guests booking our properties is 25.
Passport Parking The City of Marblehead offers paid parking lots. You can download the Passport Parking app and have the ability to pay for parking without leaving the comforts of Sailors Aweigh. Below please find some useful information on the pay by plate kiosks, times of operations, locations, and more.
WHERE ARE THE PAY BY PLATE KIOSKS?
There are one or more kiosks in each parking lot. There is an easily identifiable sign “Pay Here” above each kiosk.
Pay at the kiosk, with cash or credit card
Pay by phone, through the Passport Parking App, available on these Play Store and Apple App Store.
Kiosks operate 24 hours/day
Free parking lots are at the Train Station and 2 Blue Lane Road on Rt 127. During the winter, meters and kiosk parking is free. All seasons, on-street parking outside of the meter and kiosk areas are free.
House Rules: Good Neighbor and Respectful Visitor Welcome! We hope you will stay with iTrip North Shore. We would be delighted to be host your visit! iTrip North Shore strives to provide excellent service and assistance.
Guests are expected to honor our House Rules to be Good Neighbors and Respectful Visitors.
Good Neighbors honor the right of Sailors Aweigh’s neighbors to peacefully enjoy their homes. iTrip North Shore's guests will:
Respect Quiet Hours: Quiet Hours are dictated by local rules and ordinances. Unless specified otherwise, quiet hours are between 10PM and 8AM.
Not Host Events or Parties: without express written approval from iTrip North Shore, do not host any parties or events.
Follow the Law: do not do anything illegal.
Respect Boundaries: Do not encroach into the neighbors’ space, including but not limited to yards, gardens, decks, patios, and parking spaces. Do not use neighbors’ amenities or take neighbor’s property, such as: furniture, grills, pools, spas, etc.
Follow Parking Instructions: Please follow all parking instructions and only use those spaces allotted to Sailors Aweigh.
Respectful Visitors: remember you are renting a private home; iTrip North Shore guests will treat Sailors Aweigh with the same or more respect that they would like shown to their belongings:
Prudent Use: instructions on how to use appliances and amenities are provided. Please use all items for their intended purpose and per instructions. Please contact iTrip Vacations North Shore Massachusetts if you have any questions.
Be Neat and Caring: please do pick up after yourselves; put trash and recycling in proper bins, do the dishes, use coasters, and leave the furniture where it belongs.
Park in Designated Areas: Please do park in driveways, parking pads and garages. Please do not park on lawns or in gardens.
Do Not Smoke or Vape: smoking or vaping of anything: cigarettes, pipes, cigars, or marijuana, requires special remediation to remove the aroma.
Do Not Tamper with Safety Sensors: iTrip North Shore homes come equipped with a variety of safety sensors, such as: exterior cameras, noise monitoring, smoke detectors, carbon monoxide detectors, and more. Respectful guests do not tamper with the owner's safety sensors.
Be Careful: where there are wet area amenities such as waterfronts, docks, pools, or hot tubs, please take care to secure the areas and take appropriate precautions.
Return Keys/Passes/Remotes: please return items as described in Check-out instructions.
Please know that violating House Rules is grounds for terminating our agreement.
Please enjoy this lovely home with respect for the home and the neighborhood.
Enjoy your stay!
Things To Do In Beverly Peabody Essex Museum
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Things to Do In Marblehead
A walk or bike ride along the Marblehead Rail Trail, a 4-mile long pathway that meanders through wooded areas and continues on into the neighboring towns of Swampscott and Salem.
A walk through the Marblehead Neck Wildlife Sanctuary, located just 1/4 mile from Sailors Aweigh, offering a one mile trail through 20 wooded acres, with the opportunity for bird and animal sightings.
A visit to Devereux Beach, Marblehead’s largest beach, which offers a playground, restaurant, picnic tables, and parking. Lifeguards on duty during specified hours.
Renting stand-up paddle boards at Riverhead Beach and exploring the boats and sites in Marblehead Harbor.
Eating in Marblehead’s many restaurants, from waterfront dining at the Landing to seafood at the Barnacle or sandwiches and pizza at Cafe Vesuvius.
A visit to one of Marblehead’s many beautiful oceanfront parks, including Chandler Hovey park (featuring the Marblehead Lighthouse), Castle Rock (for the climb and the views), and Fort Sewall (for the scenery and the history).
A visit to one of Marblehead’s many historical sites, including the Jeremiah Lee Mansion, the King Hooper Mansion, Old Burial Hill, the Old Townhouse, and Abbot Hall (home of the painting the Spirit of ’76).
Wandering through Marblehead’s two quaint shopping districts, one newer and one dating from the 1600s, with both offering a variety of dining and shopping options.
Exploring the older part of Marblehead at the far end of the peninsula, with many houses bearing plaques dating from the 1600s and providing information about the original owner’s name and occupation.
A visit to one of Marblehead’s many playgrounds, including Gatchell’s, Hobbs, and Gerry, with climbing structures and slides as well as open fields for children and adults to enjoy.
A movie right in the heart of Marblehead at the Warwick Theater.
Things to Do in Salem
The Salem Witch Museum, Witch House, and Witch Dungeon offer educational insights into the witch trials that took place in Salem in the 1600s.
The world class Peabody Essex Museum with a variety of unique exhibitions from around the world.
The House of the Seven Gables, well known as the setting of Nathaniel Hawthorne’s novel of the same name.
Pickering Wharf, a harbourfront shopping and dining district offering views of beautiful boats and the opportunity to stroll to the end of the nearby pier, ideally after first stopping by Captain Dusty’s for some homemade ice cream.
Salem Willows, which offers ocean front parks, beaches, and walking paths as well as an old fashioned arcade, including a carousel and miniature golf course.
A variety of specialty walking tours are available, many focusing on the Salem Witch Trials.
Boat and trolley tours also offer the opportunity to explore Salem by land or water and learn about the town’s history.
Coffee Maker Sailors Aweigh has a drip coffee maker.
Family Friendly Sailors Aweigh welcomes families and children.
Window AC Sailors Aweigh Air Conditioning is provided using window air conditioners. Air Conditioners are spread throughout the property to provide sufficient cooling. Bedrooms and living areas will have AC Units, seasonally: Window Air Conditioners are installed in May and removed in September.
All window ACs have both cooling and fan modes. So fans are provided as part of the AC unit.
Welcome Pack & Linens
As a token of our appreciation, a Welcome Pack awaits you in the fridge.
Beds are made with freshly laundered linens. Clean towels for each registered guest are placed on the beds. Each accommodation comes with starter pack of 1 roll of paper towels, each bathroom will have at least 1 spare roll of toilet paper. A starter pack of coffee, cleaning supplies, and hand soap is also provided.
Items you should bring with you: Extra paper products, beach towels, beach chairs, sunscreen, toiletries, food, beverages, and any other essentials and assundries to make your vacation enjoyable.

