Holiday houses in Wingaersheek Beach

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Top-rated holiday rentals in Wingaersheek Beach

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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

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.

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!

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, 122 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!

Top Guest favourite
Apartment in Rockport
4.99 out of 5 average rating, 86 reviews

Oceanfront Stay 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.

Guest favourite
A charming blue house is positioned over water, featuring multiple outdoor spaces. An expansive deck is visible with a red umbrella and seating, while two kayaks rest on a nearby floating dock. Surrounding greenery enhances the natural setting.
Home in Gloucester
4.95 out of 5 average rating, 42 reviews

Oceanfront Dock Escape ~ Kayaks & Paddleboards

This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, MA! • 13-minute drive to Wingaersheek Beach • 10-minute drive to Downtown Main Street in Gloucester • 2 inflatable Paddleboards • 4 Kayaks Available! • Outdoor Patio w/ Oceanfront Views • Large Jenga set • Fully Stocked Kitchen • Multiple Outdoor Spaces: Balcony/Deck • Family Friendly- Pack n Play & High Chair • Beach Essentials: Chairs, Umbrellas, Life Vests, Towels

Top Guest favourite
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
4.99 out of 5 average rating, 222 reviews

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 New England coast. Come fall in love with charming Rockport!

Guest favourite
A quaint stone cottage is surrounded by lush greenery and colorful flowers, with a well-maintained garden featuring clusters of purple blooms. The cottage's rustic charm is complemented by a sloped lawn and mature trees, creating a serene outdoor atmosphere.
Guesthouse in Gloucester
4.93 out of 5 average rating, 123 reviews

Plum Cove Cottage with king suite!

A quaint 1900's cottage Plum Cove beach is just 500 ft away! The full gourmet kitchen has granite counters and stainless steel appliances. There is also a spa shower, romantic king bedroom with maple spiral stairs and 3 skylights which provide amazing light throughout. Watch the spectacular sunsets voted one of the best in the world by National Geographic. This is the premier location to begin your exploration of Cape Ann. Beach umbrellas and chairs provided.

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, 64 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

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, 496 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.

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.

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, 144 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.

Popular amenities for Wingaersheek Beach holiday rentals