Waterfront vacation 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, 158 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, 230 reviews

Holiday fun & waterviews in the heart of 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, 144 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, 165 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.

Apartment 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!

4.86 out of 5 average rating, 125 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.

Apartment 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.

4.97 out of 5 average rating, 304 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, 421 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.

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.

4.93 out of 5 average rating, 173 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, 335 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.

4.99 out of 5 average rating, 207 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.

Condo in Rockport

Bearskin Neck Rockport ★ Amazing Views ★ Parking

From the deck of this New England vacation retreat enjoy amazing views of Rockport Harbor and the iconic Motif #1. Steps from delightful shops, restaurants, and ice cream/coffee, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport on Bearskin Neck. Enjoy beautiful ocean breezes with coffee or cocktails on the deck of this sweet beach retreat nestled on the N.E. coast. Come fall in love with charming Rockport!

4.86 out of 5 average rating, 320 reviews

A cozy living area features a light gray sectional sofa with decorative pillows. A small star decoration hangs on the wall, and a flat-screen TV is positioned on a dark wooden console. Soft natural light enters from the adjacent room, creating a welcoming ambiance.

Apartment in Ipswich

Comfortable house, close to beach and downton IPSW

This home has all you need for your business or gateway in New England . With everything a Nice hotel has to offer ,this will be your home away from home. The Kitchen is fully equipped and you will have the entire place for yourself . You will be in walking distance to the train station in dowtown Ipswich and biking distance to the beach and Crane's Castle. Also you can explore Cannoing or paddling on the nearby Ipswich River.

Popular amenities for Gloucester waterfront rentals

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.

Apartment in Waltham

4.83 out of 5 average rating, 115 reviews

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

4.97 out of 5 average rating, 108 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.

Apartment in Nahant

The Blue Pearl

4.94 out of 5 average rating, 156 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.

Apartment in Winthrop

Newly Renovated Ocean View 2 Bdrm Apt

4.99 out of 5 average rating, 116 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.

Apartment in Portsmouth

Tugboat Vista | 2 Bedroom | Downtown Portsmouth

The living room features large glass doors that open to a scenic ocean view. A gray sofa and a woven rug create a cozy seating area, complemented by a modern red chair and a dark coffee table. Natural light fills the space, enhancing the tranquil ambiance.

5 out of 5 average rating, 36 reviews

The Pearl, Apt. #2

4.91 out of 5 average rating, 138 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.

Apartment in Lynn

Spacious 2B Entire Home near Boston, Salem& Encore

4.97 out of 5 average rating, 197 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.

Apartment in Salem

Mariam’s On Becket

Waterfront house rentals

4.96 out of 5 average rating, 306 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!

4.85 out of 5 average rating, 615 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

4.96 out of 5 average rating, 84 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, 177 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!

4.94 out of 5 average rating, 16 reviews

A waterfront home is shown with expansive windows, situated directly by the water. A private dock extends toward the water, accompanied by a set of stairs leading down from the deck. Nearby, a separate guest house is visible, framed by greenery.

Home in Gloucester

Stay at Rocky Neck

4.92 out of 5 average rating, 102 reviews

An open concept living area features a blue sectional sofa, a white coffee table, and a wall-mounted TV displaying a movie. Natural light fills the space through windows, highlighting kitchen cabinetry and a dining table for four in the background.

Home in Gloucester

Seaside Home|Sleeps 7|Plum Cove Beach+Rockport!

5 out of 5 average rating, 107 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

4.89 out of 5 average rating, 113 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

*Spooky 2BR Halloween|HocusPocus|Parking+Downtown

Waterfront condo rentals

A serene beach scene showcases soft waves gently lapping against the shoreline. Light sand is dotted with smooth rocks, while the horizon features clear blue skies meeting the ocean. A few distant figures can be seen enjoying the beach, contributing to a peaceful atmosphere.

4.98 out of 5 average rating, 166 reviews

Beachfront Getaway

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, 116 reviews

Cozy up in our oceanfront 2BR condo Hampton Beach

4.9 out of 5 average rating, 125 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.

Condo in Rockport

The Nest - The Heart of Bearskin Neck

4.97 out of 5 average rating, 110 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.

Condo in Rockport

Rockport Downtown Sleeps 5 Take The Train To Salem

4.96 out of 5 average rating, 107 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.

Condo in Salisbury

Oceanfront Penthouse at Salisbury Beaches

4.97 out of 5 average rating, 214 reviews

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.

Condo in Badger's Island

Badgers Island Condo- Sweeping Portsmouth Views #1

Superhost

A cozy studio space is accentuated by light wood paneling and vibrant coastal decor. A spacious bed is complemented by a plush sofa and dining table, creating a functional area. Large windows frame panoramic views of the ocean, allowing natural light to fill the room.

4.93 out of 5 average rating, 140 reviews

Oceanfront, private balcony, panoramic view Ocean