1 / 50

Sailors Aweigh

House in Marblehead, MA

6 guests·3 bedrooms·3 bathrooms
4.7 · 13 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Sprawling backyard with deck, croquet, and social outdoor dining.

Location & Accessibility

Location & Accessibility

Walk to beach, pubs, and shops—central Marblehead access.

Style & Comfort

Style & Comfort

Cozy sunroom and fireplace create welcoming, conversation-friendly evenings.

Property details

Want a uniquely Witch City Experience? Stay with us and enjoy special pricing for a group psychic reading or seance. Looking for that perfect vacation rental? Looking for an amazing outdoor space? Looking for a cozy home that is close to everything – park your car and walk to the beach, restaurants, pubs, and shops? Welcome to Sailors Aweigh, a Marblehead vacation home with all of the above and more! - An amazing outdoor space including a large deck, BBQ, dining space, gathering space with Adirondack chairs, and the perfect large lawn and croquet. - A kitchen furnished with everything you need: full sized stove, side-by-side fridge, large washer & dryer, and tons of space - A cozy sunroom with large screen Smart TV and plenty of board games for playful fun. - Cozy living open space with decorative fireplace – a great space for conversation or quiet relaxation. - Private workspace in the dedicated office with desk, desk chair, and desk light - Perfect for 3 couples with 3 Bedrooms each with a queen bed, and off-street parking for 3 cars. As you enter Sailors Aweigh, you’ll be pleased with the open space and main floor living space. You enter the large bright kitchen with plenty of space for preparing meals. To your right, enter the dining room with dining space for 6. Off the dining room, one can enter the sunroom with big screen Smart TV, and the living room with decorative fireplace. A powder room off the dining room rounds out the first-floor features. Check out the large collection of board games – just perfect for those couple competitions. The spacious kitchen features: - full sized appliances: electric stove with large oven, dishwasher, side-by-side fridge, and large microwave - Make your favorite coffee with the drip coffee maker - Tons of pots, pans, knives, utensils, and kitchen wares. - Large Front-load washer and dryer - Breakfast nook with pub height seating for two. Everything you need to prepare a fabulous meal! As you exit the kitchen, enter the dining room with dining table for 6. In the sunroom, you’re surrounded by 3 walls of windows. Sunlight glistens off the cozy furnishings and views of Sailors Aweigh expansive outdoor space. Sailors Aweigh back yard is absolutely amazing - full of fun gathering spaces: - Outdoor shower – rinse off the sea salt while enjoying a beautiful summer sky - Deck with a Dining Table: enjoy that perfect vacation morning: coffee with birdsong – so soothing - Gas Grill for those great BBQ dinners. - Relax & take in the sun on the Adirondack Chairs. - Feel free to set-up croquet on the expansive lawn. _____ Sailors Aweigh Sleeping arrangements: 3 Bedrooms Sleeps 6 Front Bedroom (Sleeps 2) - Queen bed bookended by 2 side tables - Bureau - Large Closet Left Side Bedroom (Sleeps 2) - Queen bed bookended by 2 side tables - Large Bureau - Closet Right Side Bedroom (Sleeps 2) - Queen bed bookended by 2 side tables - Large Bureau - Closet _____ Sailors Aweigh Accommodation Highlights - Amazing backyard and outdoor living space - Outdoor Deck with dining area and gas grill - Expansive backyard - Well-furnished kitchen with full sized appliances: dishwasher, stove, fridge, and laundry - Drip Coffee Maker - 3 bedroom - 1 Full Bathroom with walk-in shower - Main floor powder room / half bathroom - 1 Large Screen Smart TV ____ Window AC Units This property is cooled with window air conditioning units. The units are installed in May and removed in September. Each window AC unit has both a cooling function and a fan function. Each room with a window AC unit; also has a fan. __________ About Marblehead Founded in 1629, Marblehead was a crucial fishing port during the American Revolution; much of its history can be discovered by navigating through the colorful, narrow streets of Old Town. Like an open-air museum, Marblehead flaunts its history not only in its well-preserved 18th-century houses and architecture, national historic landmarks and local shops are sprinkled throughout the town. After meandering amongst the quaint Colonial houses, take a tour through Marblehead Neck, which leads to the lighthouse. Marvel at the breathtaking views of Marblehead Harbor, birthplace of the US Navy, & a major sailing capital. Marblehead’s most popular beach, Devereux, has plenty of picnic tables, playgrounds, and on-site restrooms. Gas House Beach is on Little Harbor. With a rocky shore and small boats anchored in tranquil, shallow water, the scene at Gas House is perfectly New England. Active visitors can enjoy a paddle at King’s Beach with views of Boston. __________ About iTrip North Shore Properties - Smoking is strictly prohibited. Guests will be fined and immediately evicted for smoking or vaping in the home or on the property. - NO PARTIES, EVENTS, PERFORMING ARTISTS OR BANDS ALLOWED AT ANY TIME. These are cause for eviction with no refund. If any damage impacts our ability to offer the home for future guests, you will be held liable. __________ Amenities: - Each of property features a starter set of supplies for guests which includes toilet paper, paper towels, dish detergent, & hand soap. - The beds are fully made & ready for your arrival with freshly laundered linens. A set of towels for each registered guest are included in the rental rate. - For family friendly homes, a luxury Pack-n-Play or other children's furnishings are available for an additional charge (as availability permits). __________ Visiting like a local means being neighborly. Please be respectful of the owner's home and considerate of the neighbors. Minimum age to book this property is : 25

Sleeping arrangements

Bedroom 1

1 Double Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

What’s included

  • Self check-in

    Self check-in

  • Parking

    Parking

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Fireplace

    Fireplace

  • Kitchen

    Kitchen

Guest reviews

Star icon 4.7 | 13 reviews
5
4
3
2
1
A

Aleyna

Star Icon 0 0Star Icon 0 1Star Icon 0 2Star Icon 0 3Star Icon 0 4

August 2026

we had a very good time, thank you Liann!

C

Catherine

Star Icon 1 0Star Icon 1 1Star Icon 1 2Star Icon 1 3Star Icon 1 4

November 2025

Wonderful house. Nice beds, good water pressure and easy to navigate to and from. Marblehead is a lovely community. House is spacious, just wish there were a few more sitting places when all 6 of us were hanging out other than the dining table. We had a great girls trip and loved visiting Salem at Halloween!!

M

Madeline

Star Icon 2 0Star Icon 2 1Star Icon 2 2Star Icon 2 3Star Icon 2 4

September 2025

This was a lovely weekend stay in Marblehead for myself and my friends attending a wedding in Salem. We felt the space was clean and the host clearly communicating everything we needed in advance. Would recommend!

K

Kate

Star Icon 3 0Star Icon 3 1Star Icon 3 2Star Icon 3 3Star Icon 3 4

September 2025

The house was clean and located a short drive from Salem. Check in and check out were easy. I would stay there again.

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 10:00am

No pets allowed

Min. age to rent: 25

No smoking

No parties

Have a question about this property?

Site Footer

Get deals directly in your inbox:

© 2026 Whimstay, Inc. All Rights Reserved. “SEIZE THE STAY” and “WHIMSTAY” are registered trademarks of Whimstay, Inc. and the W Logo is a trademark of Whimstay, Inc.