3 Bedroom Vacation Rentals In Marblehead, MA

Everything here for a perfect multi-family vacation in Marblehead! Two spectacular beaches are a short walk away and beach cart/chairs/cooler/umbrella are provided. Restaurants and shops are within short walks, as are grocery stores and public transportation. brbrFive bedrooms sleep 12, who can all enjo the large family room with sunny deck, Twp full baths, and formal and informal dining areas. Quiet spaces to spread out in small groups . Spectacular game room fills summy 3rd floor with TV viewing area, ping pong, foosball, and work desk, all lit by huge skylights. Laundry room is convenient to in-kitchen eating area. Formal living room with cp,fprtab;e spfabed and cozy den with single bed are remote from the large family room for quiet work or conversations. Sunny huge windows throughout house provide views of quaint historic neighborhood and backyard garden. brbrRedd's Pond next door is perfect for children's fishing and model silboats or for visits to the adjacent Old Burial Hill cemetery, with unique carved 17th century gravestones. brbrRear of house is faces Dunn's Lane, the narrowest street in Marblehead and on way to the historic district with shops and restaurants. Fabulous seafood restaurants as well as yacht clubs and boat rentals are nearby. brbrMany concerts, plays, and movies are available throughout the year, and especially during the Marblehead Festival of the Arts in July.

Walkable to Everything Great about Marblehead! Perfect for multiple families -12

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$927.11

Come stay in our refurbished four bedroom, 2.5 bathroom, house on a quiet, beautiful private way in Marblehead, MA. You can sip cocktails on the deck overlooking the pond as the sun sets while your children feed the ducks and play with the turtles, frogs and fish of the pond.brbrYou can stroll to the private rocky beach a short five minute walk away or drive 5 minutes to the sandy town beach where you can enjoy chowder and a lobster while your children build sandcastles or play on the playground equipment.brbrIn addition to all Marblehead has to offer, we are minutes from downtown Salem, the Witch City, home of the renowned Peabody Essex museum, and site of month-long celebrations in October leading up to Halloween.brbrMarblehead is a short 40 minute drive to Boston where you can stroll Newbury St., visit Faneuil Hall, or visit Fenway Park.brbrKeywords: House

Charming, beloved house sleeps 8, with huge deck over pond & close to the ocean

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$2513.25

Rockcleft by the Sea offers guests luxurious and spacious accommodations in a stunning ocean front location. Situated in a small picturesque community just north of Boston, Massachusetts, this vacation home features wraparound ocean views, a gourmet kitchen, multiple gathering areas, comfortable ensuite bedrooms with down comforters, and numerous special touches to ensure a relaxing family gathering or a productive executive retreat.brbr________________brGathering SpacesbrThe living room, with its soaring ceilings and panoramic ocean views, is the central focal point of the home. A large coffee table is surrounded by welcoming couches and plush swivel chairs, inviting guests to curl up with a book or gather for conversation. A wooden chess set offers the opportunity for a friendly game while watching the ocean spray leap over the rocks just outside the window.brbrThe family room, separated from the living room by sliding glass doors, also offers expansive ocean views. Two screened doors allow in the ocean breeze and offer access to multiple backyard patios. A 58 inch flat screen television set rises from the floor with the touch of a button, allowing for unimpeded views when the TV is retracted. brbrRockcleft’s dining area offers the ideal setting for leisurely family meals, with an oval shaped table with seating for eight, plus room for an additional four and two large buffet tables.brbrThe gourmet kitchen offers space for more casual dining overlooking the ocean, with a large center island (bar-style seating for two) and a circular kitchen table that can accommodate eight. Other accouterments include a SubZero refrigerator, a wine cooler, a convection oven and microwave, a dishwasher, two sinks, and a gas stovetop. The kitchen is fully stocked with all necessary cooking and serving implements as well as small appliances including a coffee maker, Keurig, blender, toaster, electric skillet, and crockpot. brbrThe playroom provides entertainment for children of every age and interest. It includes a foosball table, mini air hockey and knock hockey sets, a train table, and a children's eat-in kitchen. The closet contains a large selection of games and toys, from Monopoly and Scrabble to Trivial Pursuit and Candyland, as well as Legos and building blocks.brbrThree powder rooms, one with a laundry closet, round out the public living spaces.brbr____________brOffice SpacesbrRockcleft also perfectly suits the needs of executives traveling with family or business associates. The spacious upstairs office includes a wraparound desk and a balcony overlooking the ocean as well as double monitors, a mouse, a keyboard, and a printer with USB-C connections for a laptop. A private powder room is attached to the upstairs executive office. brbrThe downstairs office serves as a small business center with landline telephone, guest computer, monitor, printer, and fax machine. brbr___________brFitness RoombrGaze at the ocean or catch the news while using the treadmill or stationary bike, both made by LifeFitness, or the HealthRider total body workout machine.brbr________________________brSleeping AccommodationsbrRockcleft offers three king-size private suites plus a four-bed bunk room, a “snoring” room attached to the first floor ocean front suite, and a daybed in the fitness room. All suites offer comfortable duvets, plush blankets and towels, large screen smart TVs, seating areas, walk-in closets, and bedside tables with reading lights. brbrOwner's Suitebr- Main bedroom: king bed and 55” smart TVbr- Snoring room: queen bed and Roku TV (Accessible through the main bedroom, the snoring room is perfect for snoring spouses, small children, or a caregiver for a guest who needs assistance.)br- Reclining leather chair and ocean front table for 2br- Expansive bathroom: water closet with toilet and bidet, 2 sinks and vanities, walk-in shower with seat, 2 shower heads (one handheld), deep soaking jetted tub for 2 with ocean viewsbrbrOcean Front Suite:br- King bed and 55” smart TVbr- Leather reclining massage chairbr- Private deck with bistro seatingbr- Bathroom: water closet, large vanity, walk-in shower with bench and handheld shower headbrbrOcean View Suite:br- King bed and 55” smart TVbr- Table with seating for 2 and rocking chairbr- Bathroom has separate powder room and bathing room with deep soaking jetted tub and shower combinationbrbrBunk Room Suite:br- 2 twin-over-full bunks and smart TVbr- Table with seating for 2br- Full bathroom with shower/tub combination.brbrFitness Room:br- Twin daybedbr- Shares bathroom with Ocean View Suitebrbr______brParkingbrRockcleft offers 2 garage and 3 driveway spots with a u-shaped drive for easy entry and exit.brbr_______brOutdoorsbrStep through the glass doors of the foyer and out onto the back deck, which extends from one side of Rockcleft to the other. Weather permitting, the deck offers several comfortable recliners and tables for drinks or snacks. A few steps down brings you to the circular flagstone patio, which boasts a round stone table with seating for eight. A series of decks lead down from the backyard to the lower patios. An outdoor grill is available during spring, summer, and fall. An outdoor hot tub is available seasonally from Memorial Day through Labor Day. For guests who request hot tub use, a $100 daily fee is charged upon arrival to cover cleaning and heating costs. brbr_______________brAbout MarbleheadbrRockcleft by the Sea is located in the seaside community of Marblehead, Massachusetts, a small town on a peninsula 15 miles north of Boston. The house itself can be found on Marblehead Neck, a smaller peninsula that is connected to the main part of Marblehead by a half-mile long causeway. The causeway is open to cars, bicycles, and pedestrians, and it affords stunning views of the Atlantic Ocean on one side and Marblehead Harbor on the other. There is much to see and do both in Marblehead and in the surrounding communities.brbrStart your tour with a walk or drive through the colorful narrow streets of downtown Marblehead. The town was founded in 1629 and served as a crucial fishing port during the American Revolution. Look out for the plaques on many of the homes showing the year of construction and original owner. brbrFrom Rockcleft, take a short walk down to Castle Rock and continue on to the Marblehead Lighthouse, a beautiful park overlooking the harbor with picnic tables and benches. In the other direction, just on the other side of the causeway, you will find Devereux Beach, which offers a playground, restaurant, and on-site restrooms. For those interested in exploring the harbor by paddleboard, rentals are available just across the street from Devereux at Riverhead Beach. brbrOther local options: a walk or bike ride along the Marblehead Rail Trail, which extends into neighboring Swampscott and Salem; a walk through the Marblehead Neck Wildlife Sanctuary located just ¼ mile from Rockcleft; a visit to historical Fort Sewall for some revolutionary history; a tour of 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 to the painting the Spirit of ‘76); and eating in some of Marblehead’s many restaurants, from waterfront dining at The Landing to seafood at The Barnacle or sandwiches and pizza at Cafe Vesuvius. brbrAlso take some time to visit nearby Salem, Massachusetts, just a 10-minute drive away, with options including: insights into the Salem witch trials at the Salem Witch Museum, Witch House, or Witch Dungeon; a visit to the world class Peabody Essex Museum with exhibitions from around the world; a tour of the House of the Seven Gables; a visit to Pickering Wharf for harbor front shopping and dining; and boat and trolley tours of Salem and nearby areas.brbr__________brHouse Rulesbr- As noted in rental agreement, a $10,000 authorization only security deposit is required PRIOR to check-in.br- A photo ID matching name on reservation is required at check-in.br- Advance permission and additional contract required for commercial filming/photography.br- Smoking is strictly prohibited. Guests will be fined and evicted for smoking or vaping anywhere on the property.br- NO PARTIES OR EVENTS PLEASE. Only the contracted number of guests allowed at any time. For your safety, video cameras are placed outside of the house. Indoor technology monitors noise and number of devices.br- Rockcleft is located in a quiet family neighborhood. Please enjoy the peace and beauty but honor our neighbor's privacy and keep noise as low as possible.br- Please see provided rental agreement for all additional rules and guidelines and ensure that you agree prior to completing your booking. We ask guests to provide a signed copy of their customized contract prior to booking confirmation.brbrTo protect this very special property, please note that violation of these rules or those outlined in rental agreement is cause for eviction with no refund and forfeiture of all rent and security deposits. Additional fees may be incurred, and guests will be held liable for lost rent if any damage impacts the ability to offer the home for future rental.brbr________brAmenitiesbr- Supplies available for guest use include toilet paper, kleenex, paper towels, sponges, dish detergent, hand soap, dishwasher pods, detergent, shampoo, body wash, and conditioner. The kitchen includes basic spices as well as salt, pepper, oil, and vinegar. Other specialty supplies, including desired food items and toiletries, can be provided upon request.br- The beds are fully made and ready for your arrival with freshly laundered linens and luxurious down comforters. A set of towels for each registered guest is provided. Beach towels are also available, along with folding chairs and an umbrella.br- For families with small children, a luxury Pack-n-Play and other children's furnishings can be arranged upon request.brbr__________brPlease NotebrMarblehead recently implemented a 6% local lodging tax that will be added to your rental rate.br

Rockcleft by the Sea: Stunning Oceanfront Mansion Offers Luxury, Comfort, Views

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$558.5

You will love this 3 bedroom house in a family friendly neighborhood with just a 2 minute walk to Green Street Woods and less than a 10 min walk to Stramski’s Playground and Beach facilities. Explore Old Town Marblehead which is minutes away and downtown Salem is only a 10 minute drive. Our home has a nicely updated kitchen that transitions to a generous open plan for the living and dining room area with beautiful hardwood flooring. There is an extra sitting area with a comfortable daybed just perfect for reading or napping on the first floor as well as a lovely bedroom with an adjacent half bath and laundry access. The second floor has two fully carpeted bedrooms and an updated spacious full bath. Love the outdoors There is a patio area and stone wall behind the house then up a few steps to an open back yard for outdoor games. Decorated with intentional New England cottage style, our home is sunny, comfortable and spacious. It's perfect for families, friends or just a peaceful get away for anyone. Great for any season. brbrDogs allowed at an additional fee. No smoking or vaping inside. No loud events or parties.

The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!

Marblehead, Massachusetts, United States

Bed

Bath

7

Sleeps

$480.87

Stay at the SeaWitch Cottage—a cozy, whimsical condo nestled in the heart of Marblehead’s historic district. This beautifully renovated third-floor apartment blends Victorian charm with playful modern touches, offering a soulful escape for families, couples, or solo travelers.brbrEnjoy peekaboo ocean views from nearly every window, stroll to nearby beaches and parks, and explore beloved local spots like Maddie’s Sail Loft, Shubie’s Market, and Java Sun Café. Salem is just a 15-minute drive away.brbrThe spacebr• 3 bright and airy bedrooms: 2 queen beds, 1 twin daybedbr• Full access to private third-floor walk-up with dedicated entrancebr• 1 parking spotbr• 2 desks / dedicated workspaces for your nomadic productivity or creative wanderingsbr• Small ocean views from nearly every roombr• Smart TV for cozy nights inbr• Fully updated kitchen with premium full-size CAFÉ appliancesbr• Original chestnut exposed beams and flooringbr• Locally crafted stained glass cabinetrybr• Designer lighting, chic wallpaper, and playful color accentsbr• Brand new bathroom fixtures and LG washer/dryerbr• Walkable to beaches, shops, galleries, and waterfront diningbr• Extremely calm and quiet ambiance despite its convenient locationbr• Every detail chosen with intention—and a touch of good witch magic brbrOriginally built in the 1600s, rebuilt in the 1800s, and lovingly restored in 2025 by a family of Massachusetts women and their community of craftspeople. This home is a celebration of history, heart, and healing. May its magic bring you comfort and clarity.brbrPlease note, that this is a third floor apartment, which grant it the water views. That said, plan on packing a bit lighter since the staircase is a bit tight.brGuest accessbrFull access to this private apartment and one parking spot.brOther things to notebrThis is an antique building (like everything in the area). That said, the windows require some elbow grease to open. This antique charm is exactly why we love it (chestnut exposed beams, original flooring, restored windows).brbrAdditionally, this is a third floor apartment, so please take note if you have mobility challenges.brbrMinimum age to book: 25

Apartment

SeaWitch Cottage – Stylish Spot by Shops & Sea

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$912.22

Enjoy this spacious, pristine, 4-bedroom home, with lots of light, in historic Marblehead. It is within walking distance of Marblehead Harbor, Historic District, Devereux Beach, coffee shops, restaurants, boutiques, and other amenities. Open concept first floor.Fully equipped kitchen. 1 king, 1 queen, 1 double, and a single bed. Large baby crib. Two full baths. Laundry facilities. Air conditioning. Large private fenced-in landscaped yard with plenty of parking. Pet friendly. It is a quiet neighborhood, a 10-minute drive to Historic Salem and 30 minutes to downtown Boston.

Elegant home in historic Marblehead.

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$1079.77

Host your next gathering in this beautiful and sunny two family home. Our High Tide guesthouse has 2 bedrooms & 1 full bath and our Low Tide guesthouse has 3 bedrooms & 2 baths to accommodate up to 14 guests. Fun bunk room w 4 XL custom beds. Private office with pullout twin sofa. Extra twin floor mattress available upon request. brbrDecks, private backyard, quiet neighborhood and just steps to all of the wonderful shops, cafes, beaches, harbor and public launch. Convenient to Boston (18 miles), Logan Airport (11 miles) and Salem's Haunted Happenings (2 miles). 45 minute drive to beautiful winery, 1 hour to closest ski mountain. brbrCat 6 Internet, central AC& heat, modern appliances including dishwashers, laundry and 2 cozy living rooms with modern Fireplaces. 3 Roku televisions on each floor. Egyptian cotton sheets, towels and amenities provided. brbrFree and convenient off street parking in driveway for 5-6 cars

Coastal Home in Prime location! Sleeps 14!

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$889.52

Enjoy poolside fun & daily nature walks! Spread out in this 4-bedroom, 1.5 bath home near Redd's Pond, nature trails and Old Town Marblehead. Beautiful exposed beams are featured in the large living and dining room area with plenty of space to play games or share some laughs. Three of the four bedrooms are located on the first floor along with one full and one half ensuite bath, making single-floor living possible. The fenced-in pool and patio area are just waiting for you to come and enjoy.brbrSleeping Arrangements (Sleeps 8):brbrPrimary Bedroom - first floor (sleeps 2)br- Queen-sized bedbr- Ensuite 1/2 bathbr- Large bureau and closetbrbrQueen Bedroom - first floor (sleeps 2)br- Queen-sized bedbr- Large bureaus and closetbr- Desk and chairbrbrTwin Bedroom - first floor (sleeps 2)br- 2 Twin-sized bedsbr- Large bureaus and large closetbrbrQueen Bedroom - second floor (sleeps 2)br- Queen-sized bedbr- Large bureaus and walk-in closetbr- Built-in drawer storagebr- Desk and chairbrbrPets must be approved by the host in advance of your stay. If approved, there is a $150 pet fee per stay. Only dogs. No cats.

Large 4-Bedroom Home with Pool, Nature Trails, Redd's Pond, Walkable to Shopping

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$707.1

Want a uniquely Witch City Experience Stay with us and enjoy special pricing for a group psychic reading or seance.brbrHistoric Elegance Meets Modern Comfort in Marblehead! Nestled in the heart of historic old town, Brackett Cottage is a mere 1-minute walk to shops and restaurants. A 5-minute walk takes you to a beach on Marblehead's famous harbor. While away a perfect day, watching sailboats and schooners soar past. brbr brbrA visit to Brackett Cottage of historic Marblehead transports the traveler back in time when world travelers were courageous and few, and America emblazoned revolutionary spirit. Brackett Cottage celebrates the libertarian spirit while showcasing the owners’ pride of Marblehead. Brackett Cottage harkens back to a time when travelers returned home with wares from long global jaunts. Each piece tells a story. Visitors are embraced by the wares of a global traveler juxtaposed with items that celebrate Marblehead’s seafaring and revolutionary history. brbr brbrBrackett Cottage elegantly encircles you with fine prints, antique style dinner ware, and nautical charts that represent Marblehead’s seafaring role in the American Revolution, War of 1812 and World War I. Immerse in the story of Marblehead, as it serves as the birthplace to the U.S. Navy, while admiring famous ships, tapestries, tables and lamps from around the world. brbr brbrThis New England colonial, built in 1810, features seafaring pieces that reflect the town's character. Each one has been hand-selected to tell the story of this home and one of the most distinct towns in Boston’s North Shore, Marblehead. brbr brbrBrackett Cottage was built by a shipwright for a shipwright – everything about this home is unique. No two rooms have the same shape or height; every room has a colonial era fireplace and a tilt earned through the centuries. Built-ins abound, and the staircase with brass rail feels more appropriate in a ship than a home. brbr brbrIf you want an elegantly appointed, unique accommodation, Brackett Cottage is the place for you. Guest note: as is typical with many colonial era homes, ceilings and doorways are a little lower than today’s standards. Tall people may need to duck through doorways. Stairways are narrow, and floors slope. brbr brbrAt Brackett Cottage, each room provides a cozy place for you to relax and reflect. brbr brbrIn the Living Room, it’s easy to imagine family, friends, and neighbors gathered around the fireplace on the couch or the swivel chairs, sharing news and stories. The fireplace with electric insert and cozy lighting provides the perfect ambience for parlor games and conversations. brbr brbrThe Dining Room welcomes guests to host elegant and intimate dinner parties, or to read by the fireplace. The dining table accommodates 4-6 with dinnerware and glassware displayed in the built-in sideboard. If the natural wood of this room could talk, the stories it would tell! brbr brbrThe Kitchen comprises full-sized appliances and all the furnishings to cook any family meal from a simple continental breakfast to a full dinner. As you exit the Kitchen you head out to the brick pathway that leads to either the stairway to Washington Street, or to the gorgeous private garden where guests enjoy al fresco dining. brbr brbrNow it’s time to grab the brass handrail and climb the ship-like stairs to the second floor where the bedrooms and bathroom await. brbr brbrIn the Master Bedroom, feel like royalty among the French Provincial décor. A king-sized bed smothered with silk bedding and pillows is adorned with classic side tables and crystal lamps. A silk slipper chair beside the fireplace provides another comfortable reading nook. Above the fireplace hangs a nod to modern times; guests can enjoy their favorite streaming services on the 50” smart flat-screen TV, courtesy of high speed internet. brbr brbrIn the Guest Bedroom, the shipwright’s hand is evident. The room feels like a colonial-era ship’s cabin with a built-in trundle bed, quirky closets, and a classic bureau. As is a common theme in this Marblehead home, there is another fireside reading nook. brbr brbrThe smallest bedroom, is outfitted as a den with a trundle day bed lined with large comfy pillows. While sleeping for 2 is possible, the room is set-up for snuggling in front of another 50” smart flat-screen TV – watch your favorite shows or play your favorite games. Shelves, hooks and a cedar chest provide storage for the guest’s belongings. brbr brbrThe full bathroom has a tile-enclosed bath/shower combination along with the usual accouterments. brbr brbr******* Brackett Cottage Highlights brbr brbrCentral Location – 1-minute walk to Marblehead Center, 4-minute walk to the beach brbrPrivate gorgeous garden with large patio and outdoor dining brbrHigh-speed WiFi brbr2 50” Smart Flat Screen TVs brbrKing sized bed in master bedroom brbrFull sized appliances: Stove, Oven, Fridge, Washer & Dryer, and dishwasher brbrParking Passes for off-street parking are available for a nominal fee. brbr brbr*** House Rules ***** brbr brbr- Smoking is strictly prohibited. Guests will be fined and immediately evicted if there is any evidence of smoking found anywhere in this home. brbr- No pets allowed! brbr brbrPlease NO PARTIES, EVENTS, PERFORMING ARTISTS OR BANDS ARE ALLOWED AT ANY TIME. These are cause for eviction with no refund and may damage our ability to offer the home for future guests exposing you to liability. brbr brbrAs with each of our iTrip North Shore properties, Brackett Cottage features a starter kit of a few-days' worth of supplies for guests that includes toilet paper, paper towels, dish detergent, & more. The beds at Brackett Cottage are fully made and ready for your arrival with freshly laundered linens. A set of towels for each person is also included in the rental rate.brbr____ brbrWindow AC Units brbrThis 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.brbr__________ brbrAbout Marblehead brbrFounded 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. brbr brbrAfter 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. brbr brbrMarblehead’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.brbr__________ brbrAbout iTrip North Shore Properties brbr- Smoking is strictly prohibited. Guests will be fined and immediately evicted for smoking or vaping in the home or on the property. brbr- NO PARTIES, EVENTS, PERFORMING ARTISTS OR BANDS ALLOWED AT ANY TIME. brbrThese 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. brbr__________ brbrAmenities: brbr- Each of property features a starter set of supplies for guests which includes toilet paper, paper towels, dish detergent, & hand soap. brbr- 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. brbr- For family friendly homes, a luxury Pack-n-Play or other children's furnishings are available for an additional charge (as availability permits). brbr__________ brbrVisiting like a local means being neighborly. Please be respectful of the owner's home and considerate of the neighbors.

Brackett Cottage: Celebrate 250 Years in Marblehead’s Historic Heart

Marblehead, Massachusetts, United States

Bed

Bath

6

Sleeps

$961.37

Come enjoy all things Old Town Marblehead has to offer. This cozy scandi-boho home is 5 min walk to restaurants, shops, beach, and the waterfront. You will love this home nestled into a private courtyard and garden with 3 outdoor seating areas, ample lawn for corn hole, outdoor movies and more. Wake up to amazing sun rises and birds chirping and cozy evenings with pink sky line.

Hygge carriage house in heart of Old Town Marblehead. Walk to everything MBHD!

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$740.01

Please be aware this home was built in 1733 and is not soundproof. Please note, this is a quiet home, running and screaming children wont be welcome, It is appreciated if you can be aware of this while you enjoy this house. Besides that I want your stay here to be very enjoyable.brbrWelcome drink of Prosecco and chocolates to start your vacation off,brLocation in the middle of downtown, walkable to all restaurants, beach, movie theatre, live music, Speak Easy, parks and much more!brbrEach room has there own TV. (2) 42 TV's. New Beach chairs, beach towels, coolers and lotion for your use. Large back yard, seats 6 on comfortable patio, 1 gas heater 1 electric, enjoy the flowers, take a breather.brbrFor the kids - children over 12 are welcome, This is not a soundproof building (built in 1733) and active children can be disruptive to others - most the time without knowing it. 12 yrs old+ children can enjoy toys and coloring books, games, squirt guns, sprinkler, bubble maker, glow in the dark frisbee, balls, plus more!brbrUpstairs:brLiving room - HD TV, sectional sofa, dining area with 6 chairs, brand new in wall electric fireplace.brKitchen - stainless steel appliances, New Ninja coffee maker, gas stove, microwave, dishwasher, fridge/freezer, granite counter tops;brBedroom 1: Full bed, TV, closet;brBedroom 2: Queen bed, HD TV, desk, laundry, 2 closets;brBathroom 1: Full with a tub;brBathroom 2: Full with a shower.brbrDownstairs:brBedroom 3: Queen bed, desk, large closet, next to brBedroom 4, also designed with a family and kids in mind with an adjoining bedroom and a trundle bed with 2 twin beds that convert to a king. A 52” HD TV games, beanbag chairs, board games, 50 coloring, pencils with books. Two accent. chairs and a table … so when the adults are relaxing upstairs it’s a great place for the kids to enjoy their space. (Also available are additional airbeds).brbrThe location of this home is right at 5 corners in Old Town and steps away from many restaurants, shops, boutiques, bike path with rental bikes - no car needed. You will be 1 mile from the beach, 10 minute drive from Salem. This property has the original foot print of the home in 1735, with an addition and a new downstairs. The original wide plank pine floors and exposed beams in the ceiling, granite counters, stainless steel appliances, gas stove, and dishwasher. Full size washer and dryer in unit with a large master bedroom Do you ever want to get away Not just to another vacation rental but REALLY GET AWAY… imagine this, step in to a historical building in Old Town, Marblehead a old New England town which originated in the 1600’s , this is where the navy originated…. long ago. And now it is an affluent town, surrounded by water and beaches, restaurants, with name plates on every building telling you about the original owner, and his profession and 5 yacht clubs last time I counted.brbrAnd then you open the door and walk into you first room and you realize you are really away … you are now in a safari, there are elephants, giraffes, tigers, and in a glance to the left and to the right you get the feeling of Mad Men but not in an office drinking cocktails, in the safari (so much better) a different place and time, on a safari, you can t believe what you are seeing…. Then you step down the hall and there is a sign on each door, and there is a Glam room. It is hot pink, light green and gold to glam it up, and who is with you Audrey Hepburn is to the right, and to the left is a mirrored gold vanity desk and tons of closets….. now this room is glamourous… hard to decide where to hang out right at the moment. Back down the hall and there is a sign on the door that looks mid-century modern, lets go in. Sure enough, each little detail screams mid-century modern and 2 closets and suite bathroom….. let’s keep moving. Now we are downstairs, and this room is all about the ocean, and how fun there is a wall with chalk board paint we can draw on, there are schools of fish swimming on the wall , glow in the dark stars on the ceiling. And a huge tv showing an ocean program, 2 twin beds, 2 bean bag chairs, (with fish and shells all over them, a siting area with 2 blue chairs and a white table, and look at the games! Twister, books, cards, puzzles, glow in the dark balls, and squirt guns! We can play with those in the yard, this place has a beautiful back yard, with 3 lilac bushes, 1 very large Hydrangea, 3 rose bushes, and Irises, and a patio which has a great siting area, a couch, 3 additional seats, lots of tables to hold my drink and 2 heat lamps to keep the chill off if necessary….. yes, this is a themed vacation rental, every room has a theme, adding more excitement to our trip. It’s a great way to really escape – if its done right, and this one is done right! Not only all this, but chocolates and lavender oil on your pillow, a bottle of Prosseco when you arrive, and a basket of everything you may left behind right there for your use. And if your looking for something different, maybe a personal chef to make you dinner, maybe a singer to entertain you.... just ask, caue this in not your ordinary vacation rental.

Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$753.98

Lowtide Guesthouse is our 3 bedroom unit in a two family home located in the ShipYard district of downtown Marblehead on the coast of New England just 12 miles from Boston’s Logan Airport. This Coastal Guest house provides modern accommodation for up to 9 people with a deck, backyard garden, free off street parking and super fast Cat-6 Wifi. This central air conditioned unit consists of 3 bedrooms, an eat in gourmet kitchen and open living room with a modern electric fireplace, 2 full bathrooms and a sunny office with a pullout sofa. Four custom XL twin bunkbeds are fun and comfy for both children and adults!brbr3 flat screen TV's are provided. So many wonderful sights are ready to explore steps out the front door of this special home in this seaside community. 2 Miles to Salem, 11 miles to Boston, close to the airport and public transportation. 45 minute drive to winery and 1 hr to local ski mountain. Walk out your door to the dock and watch the lobstermen hard at work!

Prime location in town w parking! Walk to beach, shops & harbor-Sleeps 9

Marblehead, Massachusetts, United States

Bed

2

Bath

9

Sleeps

$1075.11

brPerfect for families, couples, reunions, business retreats, and wedding groupsbrbrWelcome to your Marblehead Coastal Escape — where New England charm meets modern luxury. This beautifully appointed 6-bedroom, 3.5-bath home offers over 4,500 sq. ft. of light-filled living space, thoughtfully designed for comfort, connection, and style. Whether you’re planning a seaside getaway, a family celebration, a group retreat, or a small wedding, this home provides the perfect backdrop for unforgettable memories.brbr Prime LocationbrbrNestled in the heart of Historic Old Town Marblehead, this home places you steps from quaint boutiques, cozy cafés, scenic harbor views, and picturesque walking trails.brSpend your days exploring the shops and galleries of Washington Street, unwind on nearby Devereux and Goldthwait Beaches (just a half-mile away), or enjoy an evening stroll through one of New England’s most charming coastal towns.brLogan International Airport (13 miles)brbrThe Spacebrbr6 bedrooms | 3.5 bathrooms — comfortably sleeps up to 14 guestsbrbrBright, open-concept living areas with soaring ceilings and abundant natural lightbrbrPrivate backyard & patio — perfect for outdoor dining, gatherings, or a small wedding ceremonybrbrFully equipped gourmet kitchen with Keurig coffee maker, toaster oven, fridge, gas-range stove & oven, microwave, breakfast bar, electric kettle, dishware/flatware, trash bags/paper towels and cooking basicsbrbrWasher/dryer, high-speed Wi-Fi, and central A/C & Heat,brbrEvery detail has been curated to make you feel right at home—from plush furnishings to coastal-inspired décor.brbrAdd a Touch of MagicbrbrMake your stay even more memorable with a unique Salem experience. Ask about exclusive guest pricing for a group psychic reading or séance, and embrace the mystical spirit of nearby Witch City.brJust minutes away, you’ll find Salem’s iconic Peabody Essex Museum, historic tours, and world-famous Halloween festivities every October.brbrExplore the AreabrbrDiscover why USA Today named Marblehead one of America’s Top 3 Best Coastal Small Towns.brbrSteeped in maritime history — the birthplace of the American NavybrbrOnly 40 minutes from Boston — perfect for day trips to Fenway Park, Faneuil Hall, or Newbury Street shopping. brbrEnjoy sailing, beachcombing, and breathtaking ocean vistas right outside your doorbrbrAccessibilitybrbrTwo-story homebrbr7 steps required to enter the propertybrbrThree full bathrooms located on the second floorbrbrOne half bathroom located on the first floorbrbrGuest AccessbrbrGuests enjoy exclusive access to the entire home and private yard during their stay.brbrParkingbrbrFree parking for up to 5 vehicles (garage + driveway).brbrSafety & SecuritybrbrYour safety matters. This property is equipped with exterior security cameras to help ensure a secure stay. None of the cameras look into any interior spaces. They record a live feed that captures video and audio only when activated by motion or when the video doorbell is pressed. brbrHouse Rules & PoliciesbrbrNo parties or large gatherings — $750 fine for violationsbrbrNo smoking indoors — $1,000 smoke remediation feebrbrFireplace is decorative only and not for guest usebrbrPet-friendly — up to 2 well-behaved pets allowed with pre-trip approval and paid pet feebrbrPlease respect our home and neighbors by maintaining a peaceful and considerate environment

Spacious 6 BR·7 Beds·3.5 BA house in charming Marblehead & Near Salem & Beaches

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$188.66

Perched atop one of Marblehead’s most charming streets, The Main House at Gingerbread Hill offers a bright and inviting retreat that perfectly blends seaside character with modern comfort. With 3 bedrooms, 2 bathrooms, and a dedicated office, this home provides the space and flexibility for extended stays—whether you’re visiting family, renovating your own home, or simply soaking up life by the coast.brbrInside, you’ll find an open floor plan filled with natural light and ocean peeks from multiple bedrooms. Thoughtful updates complement original details, creating a warm and welcoming atmosphere throughout.

Beautiful Seaside House in Marblehead

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$456.42

Large and sunny 3 bedroom apartment in the heart of downtown Marblehead. Walk to restaurants, movies, ice cream, entertainment, the beach, and more! Dine on the deck and observe the sights and sounds of beautiful Marblehead. brbrThis unit is equipped with three queen beds and a pullout sofa. There is a fully stocked kitchen, in unit laundry, and central AC to go along with your dedicated parking space.brbr2nd floor unit - must climb exterior stairs. There is also an auto body shop below this unit and some noise can be heard during their business hours.

Apartment

Downtown Marblehead 3brm

Marblehead, Massachusetts, United States

Bed

Bath

8

Sleeps

$392.07

Presenting the newly restored Robert Morgan House. Located in the heart of Marblehead's Old & Historic district and walking distance to local shops, restaurants, the harbor and beaches, this bright and charming 3 bedroom and 1 bath condo is a masterful blend of historic detail and modern design. Located on the first floor, amenities include a private entrance, covered front porch, living area, dining for 6, walk-in shower, a nicely appointed kitchen, workspace, and dedicated off-street parking.brbrThe Robert Morgan House, a new sister property to the highly rated Samuel Tucker House, is located in the center of Marblehead's Old & Historic District and the unit has just undergone a thoughtful renovation and restoration project. Guests will have full access to the first floor unit and the covered front porch. The large kitchen with new stainless steel appliances also has a dining table that can seat up to (6) guests comfortably. The living room has ample space to play games and has a flat screen TV for additional entertainment. The property has (3) bedrooms: (2) bedrooms have queen size beds and plenty of clothing storage for longer stays, the third bedroom has a dedicated work space, storage, and sleeps two (it has a twin size day-bed and another twin size trundle bed tucked below). The bathroom has a walk-in shower and vanity with storage. The space has everything you need to enjoy your Marblehead stay.

Condo

Robert Morgan House - Old Town Luxury 3 Bed Condo

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$436.75

This sun-filled home is just minutes from beaches, downtown Marblehead and Salem. Enjoy the open-concept kitchen, living and dining area with a wood-burning fireplace and 20ft high vaulted ceiling. West-facing glass sliding doors open onto the home’s main deck. Dine al fresco above a lovely backyard and wooded area complete with a hot tub, grill, fire pit and heat lamp. 3 large bedrooms comfortably sleeps 6 people, with an extra futon in the loft for children. Pet-friendly!

3 bedroom house near Salem, walk to beaches

Marblehead, Massachusetts, United States

Bed

Bath

Sleeps

$751.19

Want a uniquely Witch City Experience Stay with us and enjoy special pricing for a group psychic reading or seance.brbrLooking 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! brbr- An amazing outdoor space including a large deck, BBQ, dining space, gathering space with Adirondack chairs, and the perfect large lawn and croquet. brbr- A kitchen furnished with everything you need: full sized stove, side-by-side fridge, large washer & dryer, and tons of space brbr- A cozy sunroom with large screen Smart TV and plenty of board games for playful fun. brbr- Cozy living open space with decorative fireplace – a great space for conversation or quiet relaxation. brbr- Private workspace in the dedicated office with desk, desk chair, and desk light brbr- Perfect for 3 couples with 3 Bedrooms each with a queen bed, and off-street parking for 3 cars. brbrAs 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. brbrThe spacious kitchen features: brbr- full sized appliances: electric stove with large oven, dishwasher, side-by-side fridge, and large microwave brbr- Make your favorite coffee with the drip coffee maker brbr- Tons of pots, pans, knives, utensils, and kitchen wares. brbr- Large Front-load washer and dryer brbr- Breakfast nook with pub height seating for two. brbrEverything you need to prepare a fabulous meal! brbrAs 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. brbrSailors Aweigh back yard is absolutely amazing - full of fun gathering spaces: brbr- Outdoor shower – rinse off the sea salt while enjoying a beautiful summer sky brbr- Deck with a Dining Table: enjoy that perfect vacation morning: coffee with birdsong – so soothing brbr- Gas Grill for those great BBQ dinners. brbr- Relax & take in the sun on the Adirondack Chairs. brbr- Feel free to set-up croquet on the expansive lawn. brbr_____ brbrSailors Aweigh Sleeping arrangements: 3 Bedrooms Sleeps 6 brbrFront Bedroom (Sleeps 2) brbr- Queen bed bookended by 2 side tables brbr- Bureau brbr- Large Closet brbr brbrLeft Side Bedroom (Sleeps 2) brbr- Queen bed bookended by 2 side tables brbr- Large Bureau brbr- Closet brbr brbrRight Side Bedroom (Sleeps 2) brbr- Queen bed bookended by 2 side tables brbr- Large Bureau brbr- Closet brbr_____ brbrSailors Aweigh Accommodation Highlights brbr- Amazing backyard and outdoor living space brbr- Outdoor Deck with dining area and gas grill brbr- Expansive backyard brbr- Well-furnished kitchen with full sized appliances: dishwasher, stove, fridge, and laundry brbr- Drip Coffee Maker brbr- 3 bedroom brbr- 1 Full Bathroom with walk-in shower brbr- Main floor powder room / half bathroom brbr- 1 Large Screen Smart TVbrbr____ brbrWindow AC Units brbrThis 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.brbr__________ brbrAbout Marblehead brbrFounded 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. brbr brbrAfter 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. brbr brbrMarblehead’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.brbr__________ brbrAbout iTrip North Shore Properties brbr- Smoking is strictly prohibited. Guests will be fined and immediately evicted for smoking or vaping in the home or on the property. brbr- NO PARTIES, EVENTS, PERFORMING ARTISTS OR BANDS ALLOWED AT ANY TIME. brbrThese 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. brbr__________ brbrAmenities: brbr- Each of property features a starter set of supplies for guests which includes toilet paper, paper towels, dish detergent, & hand soap. brbr- 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. brbr- For family friendly homes, a luxury Pack-n-Play or other children's furnishings are available for an additional charge (as availability permits). brbr__________ brbrVisiting like a local means being neighborly. Please be respectful of the owner's home and considerate of the neighbors.

Sailors Aweigh: Marblehead 3BR Retreat with Outdoor Space Near Harbor & Beaches

Marblehead, Massachusetts, United States

Bed

Bath

6

Sleeps

$414.44

This historic 3 bedroom fully furnished house offers lots of space for enjoying your stay with easy access to shops, restaurants, harbor, local theater, museums, waterfront parks and beautiful downtown areas! The main living floor has a full eat-in kitchen (granite & stainless), pantry, formal dining room, open foyer, attractive living room (with TV over the fireplace), full bath, & laundry. WIFI and cable included. Light and airy, the master bedroom (king bed) looks out over historic 'old town’ and Abbott Hall. The large second bedroom features a queen bed. The bedrooms both open to a full bath with a claw-foot tub/ shower. A very large and cozy 3rd floor bedroom has a full bed, 2 windows and a skylight. This home has been thoughtfully updated over the years, preserving most of the historic features and extensive woodwork. There is a modest side yard with a deck (with grill), brick patio, putting green, and small grass area. At the rear entry there is a porch. Garage parking available. Rent by week, month or annual.

Charming downtown home in the center of Historic Marblehead: 5min walk to harbor

Marblehead, Massachusetts, United States