Holiday houses in Wingaersheek Beach

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 Bed Water View w/ 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.

Retreat to tranquility - water views

Kick back and relax in this calm, stylish space. Look out to gloucester harbor from the big front porch. Look out to river views out the back porch. Two bedrooms, one smaller than the other. One full bathroom with tub/shower and laundry. One parking space is guaranteed but lots of off street parking. Less than a mile to downtown with shops and amazing restaurants. This unit is located on the top/3rd floor and will entirely be yours. Gloucester offers beaches, restaurants, art galleries.

PVT Waterfront Deck|Firepit|Workspace|Free Parking

Welcome to your waterfront escape in Gloucester! Nestled along the a portion of the tidal Annisquam River, this professionally designed 3-bedroom home offers the perfect mix of relaxation and functionality for families and business travelers. Enjoy stunning tidal views, a private desk for remote work, and a fully loaded kitchen. Unwind by the electric fireplace, gather on the large private deck with a gas firepit, or explore nearby shops, restaurants, and beaches. Free parking included!

Sunset Serenity-Entire Cozy Home-30 min to Salem

Imagine yourself waking up to the waves, enjoying a cup of coffee and watching boats travel between the Annisquam River and Gloucester Harbor. It’s an invitation to an unparalleled waterfront experience. Sunset Serenity offers 1,000 Sq Ft 2 beds 2 baths with one vehicle driveway. Our 1st floor features a spacious kitchen, open concept dining and living area. Upstairs offers 2 bedrooms with water view and full bath with clawfoot tub. Just minutes to downtown and 30 minutes to Salem.

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!

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

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.

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.

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.

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

Oceanfront Rockport Getaway with Loft & Views

Beautifully renovated top-floor apartment in the heart of Rockport’s historic downtown, set right on the water. This light-filled retreat features a private deck with ocean views, one dedicated parking space, and direct seasonal private access to Front Beach via a staircase on the property. Please also consider our two other apartments in same building. See host profile for details or contact us!