Holiday houses in Wingaersheek Beach

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Top-rated holiday rentals in Wingaersheek Beach

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

French doors open into a cozy living area where a sectional sofa is visible. A small green table with a bouquet of flowers sits in front, while sunlight illuminates the space. Outside, garden views reveal lounge chairs and vibrant flowers.

Guesthouse in Annisquam

4.96 out of 5 average rating, 308 reviews

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

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Top Guest favourite

A wooden dock extends into calm waters, reflecting the vibrant colors of the sunset. Surrounding marshlands are visible in the distance, while gentle clouds drift across the sky. The scene evokes a sense of serenity and connection to nature.

Home in Gloucester

4.95 out of 5 average rating, 43 reviews

Evensong: Lovely Oceanview Retreat with Dock

Unobstructed water views in this newly renovated "walls of glass" home boasting panoramic views of the Mill River, Anisquam, Wingaersheek Beach & beyond. Enjoy our dock (removed in Winter), shared with our neighbors below, and feel free to bring kayaks or paddleboards along. 1,600 square ft open concept home with 3 beds/3 baths. Large roof deck overlooking the water. Owners live nearby & also have a basement apartment (with separate entrance) at the property. Available for questions/requests.

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Top Guest favourite

Apartment in Rockport

5.0 out of 5 average rating, 10 reviews

Waterfront Condo/Heart Of Rockport/Bearskin Neck

Effortless coastal living in the heart of Rockport! This freshly refurbished 1-bed, 1-bath garden-level condo features an open-concept living, dining & kitchen area—bright, inviting & ready for your perfect getaway. Modern bath, in-unit washer/dryer & rare off-street parking included. Steps to Rockport's shops, dining, harbor, beaches & iconic Bearskin Neck. Stroll to Motif No. 1, fresh seafood & art galleries. Easy train to Boston. Perfect weekend escape or summer retreat. Come enjoy Rockport!

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Guest favourite

Cottage in Rockport

4.93 out of 5 average rating, 28 reviews

Cozy Oceanfront Beach Cottage - Walk to Downtown

Escape from reality to this intimate, coastal cottage located across the street from picturesque Back Beach and just a short walk to the galleries, shopping, and restaurants of Bearskin Neck. Imagine waking up to breathtaking ocean views and enjoying your morning coffee on the patio before heading across the street to relax and unwind on the beach. This seaside haven blends charm with modern comfort, perfect for couples, small families, or solo travelers looking to relax and explore Cape Ann.

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Top Guest favourite

The exterior of the three-story townhome is presented, featuring a modern design with multiple large windows and balconies. The property is surrounded by well-maintained grass and a paved driveway leading to garages. Nearby beach homes are visible in the background.

Townhouse in Gloucester

5.0 out of 5 average rating, 27 reviews

Luxury Portside Townhome Steps to Niles Beach

Escape to Niles Beach and experience the ultimate coastal getaway in our inviting 3 bedroom 3 1/2 bath townhome, just a short walk away from the serene Niles Beach in Gloucester. Perfectly situated for families, couples or friends looking to unwind by the sea. Explore Gloucester's historic harbor and waterfront, discover local seafood dining options and charming shops in downtown or take a scenic walk along Cape Ann's beautiful coastline. Book NOW and Experience the Magic of Gloucester!

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Top Guest favourite

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

4.95 out of 5 average rating, 123 reviews

Waterfront Downtown Apartment • Walk Everywhere

Dreaming of a magical seaside getaway? Our charming eco-apartment in the Dream House awaits you! A beach lover's paradise, we're located directly on the ocean in the heart of downtown on Bearskin Neck. Watch the sunset from our amazing windows overlooking the harbor. Park the car and walk to shopping, dining, art galleries, Front Beach and Motif #1. Accessible by train and easy to get to from Boston and Salem. Make a trip to this charming New England seaside village a priority!

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Top Guest favourite

Apartment in Rockport

4.99 out of 5 average rating, 86 reviews

Oceanfront Retreat w/ Deck & Parking

• Private deck with ocean view • Parking • Steps to Front Beach • Walk to Bearskin Neck • Pet friendly • 15-minute walk to commuter rail • Contemporary art gallery on site Beautifully renovated, light-filled top-floor apartment on the water in historic downtown Rockport. Enjoy a private ocean-view deck, one dedicated parking space, and seasonal private access to Front Beach. One of three guest apartments at The Pearl, located just behind Thalassa, our contemporary art gallery.

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Guest favourite

Apartment in Rockport

5.0 out of 5 average rating, 7 reviews

Stay at Front Beach

Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ Rare waterfront condo perched over Front Beach with harbor views ✓ Steps from Bearskin Neck, downtown Rockport, shops, galleries, and dining ✓ Bright classic coastal home with water views from nearly every room ✓ Private deck overlooking the beach, perfect for morning coffee or sunset drinks See more photos, video tours, and local recommendations on IG @staycapeann.

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Top Guest favourite

The spacious bedroom features a king-size bed with a neutral-toned blanket. Soft lighting from bedside lamps creates a cozy atmosphere. Three windows allow natural light to fill the room, with views of the surrounding greenery, enhancing the airy feel of the space.

Home in Rockport

4.95 out of 5 average rating, 65 reviews

Dog Friendly 2BR Home Walk to Beach+Bearskin Neck

*INQUIRE ON WINTER RENTAL ☀5 Min Walk to Front or Back Beach ☀ Reserved parking just steps to downtown Rockport - shops, restaurants, beaches and galleries ☀ Sleeps 5; 2 bedrooms, 1 KING and 1 Queen ☀ Perfect setup for families - includes an extra twin sized air mattress and toys in the living room ☀ Newly Renovated Bathrooms ☀ Fully-equipped kitchen with eat-in bar ☀ Hi-Speed Wi-Fi and Roku Smart TV ☀ Central AC for hot summer days ☀30 Min Drive to Salem

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Top Guest favourite

A charming log cabin is surrounded by lush greenery. Two miniature horses graze leisurely on the grass in front of the cabin, which features a covered porch and simple landscaping with flowers. Sunlight filters through the trees, highlighting the serene woodland setting.

Cabin in Rockport

4.97 out of 5 average rating, 497 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

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Top Guest favourite

A historic Colonial home is depicted with dark wooden siding and multiple windows. The structure features a central door, surrounded by evenly spaced windows on the front facade. Trees and greenery are visible in the surrounding yard, under a bright blue sky.

Home in Gloucester

5.0 out of 5 average rating, 31 reviews

William Haskell House First Period Colonial Home

A First Period Colonial American experience in beautiful Gloucester, Massachusetts! As you step through the threshold of this sensitively restored 1680 residence, you are transported to an earlier time—immersed in the history of the home and the area. This listing reserves all four rooms in the house: Parlor Chamber, North Ell, the Spinning Room and The Gambrell Bedroom. As well as access to the kitchen and lounge area that has a television.

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Guest favourite

An open-concept living area is highlighted by a modern kitchen featuring a large island with seating for four. A spacious seating area with a blue couch complements the dining space, while a sliding door leads to an outdoor patio. Ample lighting enhances the contemporary design.

Apartment in Rockport

4.88 out of 5 average rating, 145 reviews

Long Beach Suites: Steps Away From Surf!

Recently built, Long Beach Suites is ready to welcome you this summer. With peaks of Long Beach, come stay in one of our two bedroom apartment suites. Expertly built with summer visitors in mind. Long Beach Suites is just steps away from Long Beach in Rockport and only ten minutes to Good Harbor. You will be staying one of four similar apartments, photos may not be of exact unit.

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