Waterfront holiday rentals in Gloucester

A balcony view reveals a tranquil harbor filled with anchored boats, framed by vibrant flowers in a planter. The clear blue sky reflects on the water, while a bustling street lined with parked cars leads towards the waterfront.

4.95 out of 5 average rating, 163 reviews

Harborside Oasis | Harbor View | Heart of Downtown

Step into Coastal Bliss at Our Rockport Apartment! 🌊🏠 Perfectly positioned just steps from Bearskin Neck, immerse yourself in unique shops 🛍️, exquisite dining 🍽️, and serene beaches 🏖️. Revel in the spectacular views of iconic Motif Number 1 from your balcony, enjoy high-speed WiFi, and a 55" Smart TV in a fully stocked kitchen. Ideal for soaking in Rockport's vibrant yet relaxing atmosphere. Note: Requires climbing stairs and can get noisy! Book your unforgettable seaside retreat today! ⚓

The image captures a serene waterfront scene with comfortable Adirondack chairs arranged on a grassy area overlooking a calm harbor. The view includes a small dock with boats and a waterfront lined with rocky formations, creating a peaceful coastal ambiance.

4.98 out of 5 average rating, 234 reviews

Winter retreat & waterviews in downtown Rockport

Rockport is charming over the holidays with lights, music and shopping! This brand new waterfront apartment is in a historic home with onsite parking & a private entrance. Galleries, restaurants, coffee shops, live music and shopping on Bearskin Neck are steps away. Features full kitchen and bathroom with new applicances and fixtures. Living room has a loveseat, swivel chair, dining table, coffee table, roku TV, games, puzzles & books. Kitchen has a fridge, stove, oven, microwave and Keurig.

The open kitchen features a large island with seating for several guests. A cozy living area is visible, with a comfortable seating arrangement and large windows allowing natural light and ocean views. Warm wood flooring complements the airy atmosphere.

4.99 out of 5 average rating, 147 reviews

4 Bed 2.5 Bath Water view Downtown with Parking

Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

4.96 out of 5 average rating, 170 reviews

A spacious living area with a plush sectional couch in a neutral tone, centered around a coffee table, invites relaxation. Large sliding glass doors frame panoramic ocean views and provide natural light. A modern gas fireplace and stylish decor enhance the cozy atmosphere.

Flat in Beachmont

Beachmont Guest Suite

Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

4.87 out of 5 average rating, 127 reviews

An expansive view of the ocean showcases rolling waves under a partially cloudy sky. A deck is visible, outfitted with outdoor seating, surrounded by lush greenery and coastal vegetation, creating a serene outdoor space.

Flat in Magnolia

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

Apartment in Hampton Beach

4.97 out of 5 average rating, 308 reviews

Seacoast Getaway

Seacoast, NH’s popularity is well-earned, with museums, the finest restaurants, spas and shopping that blend perfectly with the Seacoast landscape. From our beautiful beaches and coastline combined with plentiful outdoor recreation, including fishing and whale watching, kite flying and more with Portsmouth, Rye, Exeter and Kittery Maine, all a short ride our beachfront condo has something for all. After a day of outdoor activity and exploring, come retire and rest in our place with a view.

4.98 out of 5 average rating, 425 reviews

A well-lit sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light fills the room from multiple windows, complemented by a cozy seating nook and shelving that adds a charming touch to the serene atmosphere.

Flat 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.

4.93 out of 5 average rating, 174 reviews

A charming white house is positioned along a rocky shore, showcasing a four-season porch with large windows that provide views of the harbor. Lush greenery surrounds the property, complementing the tranquil water scene with boats in the distance.

Home in Gloucester

Wonderful Rocky Neck home on Gloucester harbor

2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.

4.92 out of 5 average rating, 231 reviews

A welcoming sign for the Rocky Neck Art Colony is displayed prominently. The sign features blue and white colors with decorative elements, including an image of a bird. Text indicates the area is one of America's oldest working art colonies, situated in historic Gloucester.

Loft in Gloucester

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2025! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

4.98 out of 5 average rating, 344 reviews

A cozy living room features a white-brick fireplace, with a functional gas flame. Stylish furniture includes a patterned armchair and a soft couch, complemented by a light-colored striped wooden floor. Large windows allow natural light and offer views of the surrounding area.

Home in Rye

*Beachfront* Vintage Coastal Cottage - Relaxation

It's always about the view and this place will leave you feeling energized and calm. Situated on premium beachfront property, this single family home has luxurious amenities like super plush towels, organic cotton bedding and touches to make your getaway feel that much Take a virtual tour here: https://bit.ly/3vK5F0G We've outfitted it with an extra screen and a setup to get you up and running. Google home and Sonos systems bring this 100 year old beauty into this century.

5 out of 5 average rating, 165 reviews

A welcoming living area showcases a large screen displaying Netflix. Two brown armchairs with throw pillows are positioned beside a modern coffee table. A cozy fireplace adds warmth, while soft gray and blue tones create a relaxing atmosphere. Natural light filters through the windows.

Home in Kittery Point

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away!

4.98 out of 5 average rating, 110 reviews

An open living space features hardwood floors and a modern aesthetic. A sleek fireplace is mounted on the wall beneath a flat-screen TV. Bar stools with orange upholstery are positioned at the kitchen island, and a glass coffee table sits on a patterned area rug.

Apartment in Gloucester

Boho Beach Condo for Ocean Escape

Enjoy a stylish experience at our centrally-located oceanfront condo. We are walkable to exquisite beaches and parks as well as downtown Gloucester where you will find a number of bars and restaurants to explore. If you feel like hanging in, share a meal/cocktail on the private deck. Perfect for a couples getaway or a group of friends looking to explore the North Shore without ever getting in your car.

Popular amenities for waterfront rentals in Gloucester

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

A cozy bedroom features a spacious bed adorned with a colorful quilt and is positioned near a large window. Sheer curtains frame the window, providing a view of the harbor and boats outside. A softly illuminated bedside lamp adds a warm touch to the room.

4.94 out of 5 average rating, 156 reviews

Spectacular Views of Rockport Harbor.

Superhost

The spacious living area features a comfortable sofa paired with a coffee table. A dining space with wooden chairs and a well-equipped kitchen is visible in the background, complemented by modern appliances and natural light from large windows.

Flat in Waltham

4.82 out of 5 average rating, 118 reviews

2bed/2bath Apt at Waltham Landing. Corner Unit

4.97 out of 5 average rating, 112 reviews

A spacious window with dual openings frames a view of the ocean and sandy beach across the street. The interior walls are painted in a calming blue, complementing the natural light that fills the room. Grassy areas can be seen in the foreground.

Flat in Nahant

The Blue Pearl

4.93 out of 5 average rating, 158 reviews

A scenic view captures a charming two-story white house overlooking the ocean, framed by a vibrant blue sky with scattered clouds. The foreground features a street with pedestrians, while vehicles are parked nearby. Greenery line the roadside, enhancing the coastal setting.

Flat in Winthrop

Newly Renovated Ocean View 2 Bdrm Apt

4.98 out of 5 average rating, 121 reviews

An open-concept living space features brick walls and wooden beams. A cozy gray sofa with decorative pillows faces a glass coffee table. The kitchen, equipped with stainless steel appliances, includes a breakfast bar with three stools, enhancing the functional design of the area.

Flat in Portsmouth

Tugboat Vista | 2 Bedroom | Downtown Portsmouth

4.91 out of 5 average rating, 140 reviews

A comfortable living room features dark leather seating arranged around a round coffee table. Light curtains frame the windows, allowing natural light to brighten the space. A contemporary artwork hangs on the wall, complemented by decorative pillows on the sofas, enhancing the room's inviting appearance.

Flat in Lynn

Spacious 2B Entire Home near Boston, Salem& Encore

A modern kitchen features a spacious quartz countertop with a view through three large windows overlooking Sandy Bay. The cabinetry is a deep blue, complemented by decorative items and a stainless-steel sink. Natural light brightens the area, enhancing the open and airy feel.

4.88 out of 5 average rating, 40 reviews

Rare Waterfront Luxury Penthouse|Bearskin Neck

4.97 out of 5 average rating, 198 reviews

A spacious living room features a comfortable sofa with yellow accent pillows and two armchairs. A coffee table rests on a decorative area rug, complemented by a potted plant. Natural light filters through light curtains, enhancing the room's inviting ambiance.

Flat in Salem

Mariam’s On Becket

Waterfront house rentals

4.96 out of 5 average rating, 309 reviews

The exterior of the cottage is visible, featuring light gray siding and multiple windows with white trim. A vibrant display of pink flowers is situated in the foreground, providing a colorful contrast to the structure.

Home in Hampton Beach

2 Bedroom Beach Bungalow, Steps from the Beach!

4.95 out of 5 average rating, 43 reviews

A sandy beach area is equipped with a gas grill, dining table, and lounge chairs under a large umbrella. Kayaks are neatly arranged along the shoreline, while a view of the calm water and distant boats is visible beneath the clear blue sky.

Home in Annisquam

Private Beach!

4.85 out of 5 average rating, 620 reviews

An outdoor screened deck is furnished with a large glass table surrounded by striped cushioned chairs. Lush greenery and flowers are seen in window boxes, with a scenic view of the Charles River in the background, showcasing the natural beauty of the surroundings.

Home in Newton

WATERFRONT-15 min to BOS/3BdRm/2BA

4.97 out of 5 average rating, 87 reviews

Two white rocking chairs sit invitingly along a stone walkway, facing a calm harbor. Reflections of colorful buildings and boats can be seen on the water's surface, framed by a vibrant sky during sunset.

Home in Rockport

Charming waterfront home. Patio, AC, Shops, Dining

4.94 out of 5 average rating, 178 reviews

A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.

Home in Salem

Quaint Little New Hampshire Lake House Getaway!

4.97 out of 5 average rating, 31 reviews

A view from a front porch captures expansive ocean waves gently crashing against rocky shores. The sky is partly cloudy, revealing patches of blue. A scenic coastal road is visible in the foreground, lined with greenery and distant homes complementing the seaside landscape.

Home in Gloucester

Luxurious 5 Bed Home Ocean View Walk Good Harbor

5 out of 5 average rating, 108 reviews

A modern blue house is nestled within lush greenery, featuring multiple large windows and a rooftop deck with an umbrella. The tranquil marshland, dotted with tall grasses, stretches into the distance under a sky filled with soft clouds.

Home in Salisbury

Pirates Hideaway - Sanctuary on the Marsh

4.9 out of 5 average rating, 118 reviews

The dining area features a wooden table with built-in seating, adorned with decorative pillows. A vibrant mural of 'Salem Massachusetts' frames the black accent wall, while natural light enters through a window covered by dark curtains.

Home in Salem

*NEW Spooky Halloween |2BR|Downtown Salem|Parking

Waterfront apartment rentals

4.99 out of 5 average rating, 210 reviews

A private deck overlooks Rockport Harbor, featuring two white Adirondack chairs with turquoise cushions. The calm water is dotted with boats, and the iconic Motif #1 is visible in the background, enhancing the coastal ambiance.

Apartment in Rockport

Bearskin Neck Rockport ★ Amazing Views ★ Parking

Apartment in Hampton Beach

Colorful kites soar in a clear sky over a sandy beach filled with people enjoying the day. Various shapes, including sea creatures, are displayed against a backdrop of beachside buildings and umbrellas, creating a lively atmosphere.

4.83 out of 5 average rating, 260 reviews

2 min. walk to beach strip, 2 parking spots & WiF

Apartment in Hampton Beach

An outdoor balcony is furnished with wooden seating and a coffee table, providing ocean views and a serene atmosphere. The nearby sandy beach can be seen in the background, framed by a clear blue sky and a gentle horizon.

4.94 out of 5 average rating, 117 reviews

Cozy up in our oceanfront 2BR condo Hampton Beach

4.9 out of 5 average rating, 126 reviews

A bright kitchen area features a sleek countertop and modern appliances. Large sliding glass doors access a balcony with scenic views. A dining table is set for four, complemented by a relaxed workspace on the side, allowing for comfortable meal preparation and enjoyment.

Apartment in Rockport

The Nest - The Heart of Bearskin Neck

4.95 out of 5 average rating, 111 reviews

Seating for two is positioned by expansive windows, offering views of the ocean and harbor at sunset. Natural light enhances the inviting atmosphere, while curtains frame the scene, highlighting the serene coastal setting.

Apartment in Rockport

Rockport Oceanfront Apartment Heart of Downtown

4.95 out of 5 average rating, 109 reviews

A sandy pathway lined with beach grass leads toward the ocean, framed by wooden fencing. Vibrant hues of orange and pink paint the sky as the sun rises over the tranquil water, creating a serene coastal scene.

Apartment in Salisbury

Oceanfront Penthouse at Salisbury Beaches

Apartment in Badger's Island

A weathered building with colorful buoys decorates its side, positioned alongside a misty waterfront. A bridge is visible in the distance, with boats navigating nearby. The cloudy sky provides a soft, muted light to this coastal scene.

4.97 out of 5 average rating, 216 reviews

Badgers Island Condo- Sweeping Portsmouth Views #1