Holiday rentals 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

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!

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!

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!

Gingerbread House | Hot Tub | Dog Friendly

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, kitchen, queen sized bed with en-suite bathroom and sun room that converts to an extra sleeping space perfect for kids. A short walk to the train for day trips to Salem, Gloucester, and Boston!

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

Lane's Cove Bijou

Kick back and relax by the cozy gas fireplace as you take in spectacular sunsets over the ocean. This calm, stylish space features a gourmet kitchen and a luxurious master bedroom suite that make this jewel of a house the perfect retreat for a couple. The spa-like master bath includes a large walk-in shower and a clawfoot tub with views of the cove. A second bedroom provides space for an additional guest. The dining table expands to comfortably seat eight for shared meals.

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.

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.

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.

Annisquam Village Abode - access to private beach

The Annisquam Village abode has everything that guests would need to be comfortable, safe and contented. The apartment is on the second floor with a private exterior entrance and parking spot. There is a one and a half flight of stairs to the second floor deck. The stairs may be a problem for persons with mobility issues and well as children under 12. We look forward and welcome having guests come and stay.