Vacation rentals in Marblehead

4.96 out of 5 average rating, 101 reviews

A vibrant outdoor scene features a brick-paved street lined with historic buildings. Cafes with umbrellas provide seating on the sidewalk, while pedestrians stroll. Potted plants add greenery to the atmosphere, under a bright blue sky with fluffy clouds.

Cottage in Newbury

Plum Island Sunset Cottage

Come to PI to stay at our renovated beach house! Enjoy daily sunsets, a short walk to the beach, ice cream, restaurants, convenience, and wild life! The house sleeps 8, with 2 queen bedrooms & 1 bunk room that sleeps 4. The perfect spot to stay to be close to Newburyport, the surf, bird watching, running, cycling, and scenic walks through the peaceful Wildlife Refuge. Please note: this is NOT a party house. It's a cottage to be enjoyed by friends & family, in respect to neighbors and our home.

4.97 out of 5 average rating, 262 reviews

The charming entrance of the cottage is framed by vibrant greenery and colorful flowers. Two wooden chairs are positioned in front of the entrance, welcoming guests. A decorative flag flutters above the door, completing the inviting scene.

Guesthouse in Annisquam

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

4.96 out of 5 average rating, 302 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest suite in Gloucester

A charming beach house is nestled among tall grasses, with a welcoming deck visible on its front. Soft evening light illuminates the exterior, highlighting the inviting atmosphere of the home. A sandy path leads from the beach to the house, suggesting easy access to the shore.

4.98 out of 5 average rating, 424 reviews

SplashLanding Private Beach Getaway in Gloucester

Jan-March 2025 monthly rentals. Must Book Summer 2025 via Airbnb website not the APP! *Can't find an opening in SplashLanding? Our 2nd unit SquishInn has openings June-Oct 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples 2 friends can join you!

4.84 out of 5 average rating, 111 reviews

An outdoor seating area features bright orange Adirondack chairs arranged around a fire pit, complemented by a shaded area provided by a large umbrella. The cottage is visible in the background, showcasing its coastal charm with fresh landscaping enhancing the inviting space.

Cottage in Newbury

Designer decorated-Sunset Bliss- Beach 3 min walk

Peaceful Plum Island cottage, renovated fall of 2018 and 2023 with New England coastal charm. Open floor plan and water views of the marsh, a short 3 minute walk to the beach. Watch the sun rise over the Atlantic and enjoy the spectacular sunset directly in front of the house for a nightly show. Walk the cottage for ice cream, Rip tide & the Sunset Club for cocktails and dinner. Beach, boating, fishing, wildlife sanctuary, and the historic downtown Newburyport all just 40 miles from Boston!

4.89 out of 5 average rating, 159 reviews

Apartment in Newburyport

Walk to Beach Playground Lighthouse North End

Welcome to this charming 3-bedroom, 1.5-bath cottage on the island's northern tip. Just steps from the beach, boardwalk, Merrimack River, playground, and Plum Island Lighthouse, this cozy retreat sleeps up to 6 guests. Discover your perfect island getaway and enjoy your morning coffee or dinner in the spacious outdoor area while taking in the sea breeze. Only a 10-minute drive from downtown Newburyport's top dining, shopping, and entertainment. Your perfect New England getaway begins here!

4.98 out of 5 average rating, 377 reviews

A multi-story coastal home is seen from a rocky shoreline, surrounded by lush greenery. Several white Adirondack chairs are positioned on the patio, enhancing outdoor relaxation. The gray exterior of the house features a large balcony with white railings, blending harmoniously with the natural landscape.

Apartment in Salem

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

4.87 out of 5 average rating, 109 reviews

An aerial view captures the scenic coastline and sandy beach lined with boats. A variety of residential buildings dot the landscape, interspersed with greenery. The neighborhood showcases the charm of coastal living, with the sea and a pier visible in the background.

Apartment in Swampscott

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

4.86 out of 5 average rating, 122 reviews

A charming exterior view features a two-story house with light grey siding and a red wooden staircase. Lush greenery surrounds the property, including flowering trees. A brick walkway leads to the front entrance, inviting visitors into the home.

Apartment in Amesbury

Private, 2bd, 1st floor unit in historic Amesbury

Your family will be close to everything when you stay at this centrally-located Antique New England getaway . Recently renovated, but tastefully original. Everything you need is within walking distance; shopping, grocery, dining, lake, short drive/ride to beach. The space is about 900sqft; 1 bathroom, king bedroom, queen bedroom, queen pull-out couch, and an additional room in which a twin bed can be put (upon request). It will comfortably hold 4 adults, but will accommodate up to 7.

4.97 out of 5 average rating, 117 reviews

The exterior of a charming two-story home is showcased, featuring wooden paneling and a welcoming wreath on the front door. A large balcony offers views of the serene harbor, surrounded by low shrubs and a path leading down to the water.

Home in Gloucester

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

4.93 out of 5 average rating, 114 reviews

Cottage in Newburyport

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

4.96 out of 5 average rating, 100 reviews

A well-maintained outdoor area is highlighted, featuring a grassy lawn leading up to stone steps. The house, adorned with dark siding, is framed by a large tree and offers a welcoming seating arrangement on the porch. Clear skies provide ample natural light.

Condo in Gloucester

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

Vacation rentals for every style

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Apartments

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Houses

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Hotels

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Popular amenities for Marblehead vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Marblehead's top sights

Peabody Essex Museum207 locals recommend

Salem Willows Park85 locals recommend

Salem Willows Amusement Park85 locals recommend

Sea Level Oyster Bar77 locals recommend

Finz71 locals recommend

Turner’s Seafood at Lyceum Hall68 locals recommend

Boutique hotels in Marblehead

Hotel room in Downtown Boston

The exterior of the Harborside Inn is displayed at dusk, showcasing its robust stone facade and illuminated signage. Outdoor seating is visible on the patio, accompanied by bright lights. The contemporary design integrates seamlessly with the historic architecture, providing a welcoming entrance.

4.87 out of 5 average rating, 124 reviews

Harborside Inn-Boutique Hotel

A historic building stands at the intersection, showcasing classic architectural details. The structure features a prominent entrance and large windows. An American flag is displayed on the rooftop, while modern buildings rise in the background, indicating the urban setting.

Hotel room in Back Bay

4.85 out of 5 average rating, 20 reviews

Copley Double Double - Copley Square Hotel

A bright and airy room features a spacious bed with a patterned blue and white blanket. A large window allows natural light to fill the space, while a desk and chair are set against the wall opposite a mounted television.

Hotel room in Salisbury

4.85 out of 5 average rating, 33 reviews

Cozy Stay | King Bed | Steps from Waterfront

4.94 out of 5 average rating, 68 reviews

A cozy outdoor space features a group gathered around a dining table beneath string lights. Lush greenery surrounds the area, while stone pathways lead through the garden. Several chairs are positioned around the table, creating an inviting atmosphere for shared meals.

Hotel room in Cambridge

(SG) Sunny single, yard-facing with shared bath

Hotel room in Downtown Boston

The illuminated tower of a historic clock building is prominently displayed against a night sky. Architectural details include intricate carvings and a circular clock face, while surrounding modern buildings create a contrasting city skyline.

New place to stay

Marriott Custom House week 3-23-2025 to 3-30-25

A functional bathroom is shown, featuring a compact layout with a sink and a toilet. The space is brightened by white tiling and a mirror above the sink. Black-and-white checkered flooring adds a classic touch to the room.

Hotel room in Cambridge

4.71 out of 5 average rating, 69 reviews

Hotel - Contemporary Room - Near T #4

The exterior of the Staypineapple Hotel is presented, featuring a brick facade with numerous large windows. A welcoming entrance is accentuated by warm lighting and potted plants. Trees line the sidewalk, adding greenery to the urban setting.

Hotel room in South End

4.72 out of 5 average rating, 29 reviews

Staypineapple Boston, South End Corner King

A cozy lounge area features soft gray chairs surrounding a round table. A fireplace is centered along the wall, complemented by a large mirror and decorative shelves. Natural light enters through multiple windows, creating an inviting atmosphere.

Hotel room in Cambridge

4.77 out of 5 average rating, 13 reviews

Prentiss House by Thatch | King Suite #9

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Other great vacation rentals in Marblehead

4.89 out of 5 average rating, 100 reviews

Home in Ipswich

Hillside Ocean View 2BR with Private Beach Access

4.95 out of 5 average rating, 21 reviews

A bright bedroom features a spacious bed dressed in crisp white linens. Three windows offer panoramic views of the water, allowing natural light to fill the space. A white shelving unit stands to the side, enhancing the room's functionality.

Home in Hull

Every room a water view updated kitchen & bath

4.84 out of 5 average rating, 31 reviews

Apartment in Brighton

The Curie-Perfect for Monthly Stays

4.98 out of 5 average rating, 194 reviews

A fire pit is surrounded by colorful adirondack chairs in a grassy area, with bright yellow flowers adding a pop of color. The view in the background includes a landscape of greenery leading to the water, suggesting a peaceful outdoor space for gatherings.

Home in Ipswich

Stagehill Beach House

4.99 out of 5 average rating, 165 reviews

A sunlit front porch is revealed, featuring comfortable seating arrangements with soft, textured cushions. A wooden coffee table sits in the center, accompanied by decorative elements such as candles. Large windows allow natural light to flood the space, complemented by greenery in potted plants.

Cottage in Newburyport

True North Cottage*Ocean side of Boat Basin!*

5 out of 5 average rating, 14 reviews

A cozy game area features a wooden table with a built-in arcade console and bright yellow buttons. Shelves lined with colorful board games are placed against one wall. Light illuminates the space, directing attention to a world map artwork and a staircase leading to the upper level.

Apartment in Salisbury

Steps Away Ocean Home

4.91 out of 5 average rating, 122 reviews

An outdoor covered porch is depicted with a round dining table surrounded by four chairs. A gas grill is positioned near a seating area that includes a couch and two lounge chairs. The home's wooden shingles provide a natural backdrop.

Home in Gloucester

Gloucester Beach House, near Good Harbor Beach!