Holiday rentals in Cape Ann

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! ⚓

Rockport Coastal Retreat Walk To Beach

Stay just steps from Rockport’s beautiful beaches, shops, and dining in this charming coastal retreat. Perfect for couples or small families, Captain’s Quarters offers comfort, convenience, and classic seaside charm in an unbeatable walkable location. Spend your days at Front Beach, exploring Bearskin Neck’s galleries and boutiques, or enjoying fresh seafood by the harbor — all within easy walking distance. Return to a peaceful space designed for relaxation after a day by the ocean. Inside you

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 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.

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.

Retreat in the Trees- walk to Cape Hedge Beach

Cozy and comfortable summer home with lots of natural light and everything you need to make your stay enjoyable. Fully equipped kitchen, washer & dryer, air conditioning, gas grill, 3 decks, outdoor showers, high speed internet , over the air TV, Netflix, Prime Video. A short 5 minute walk to Cape Hedge Beach, 45 minute walk to Bearskin Neck. There is also lots of great sightseeing, history, boating, and restaurants all a short drive away. MA Room Occupancy Tax certificate C0104592520

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.

Rockport Oceanfront Apartment Heart of Downtown

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. Steps to shopping, dining, art galleries, Front Beach and Motif #1. A short drive to Halibut Point for wonderful walks and an easy train ride or drive to Salem. Make a trip to this delightful seaside village a priority!

Charming Toe-Hold, A Short Walk to Town and Beach

Toe-Hold is a wonderful year-round 1846 home with plenty of rooms, reading nooks and quiet spaces for family and friends of all backgrounds to eat and play together. The gorgeous beaches and picturesque downtown, great restaurants, art galleries and shops for the whole family, are within 10-15 minute walk. Rockport is one of the oldest art colonies in the US, and home to generations of fishermen. Day trips by car or train to Boston and other beautiful historic towns.

The Driftwood|2 Levels|Soaking Tub|Steps to Beach

Inquire about our winter rental rates! • Professionally furnished space • Stocked with Family Friendly Amenities • Steps to Front Beach, Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu • Private off street parking spot for 2 cars • High Speed Wi-Fi and Smart TV • 10 minute walk from commuter rail to Boston • Fully stocked and renovated kitchen • 2 levels • 2 KING size memory foam beds • Convenient EV charging right across the street

Pleasant Place

Pleasant Place is a spacious, clean and centrally located spot to spend time with your family and friends. It has two bedrooms, two full bathrooms and a pull out couch. Sun soaked in natural light, it boasts a newly renovated kitchen, granite island, large dining room and a charming family room with views of the Rockport harbor. Walk downtown, to the beach, or drive around town and take advantage of your own parking spot in the busy summer.

Hidden Gem! Short term rental steps from 2 beaches

Hidden Gem! Short term seaside rental. Lovely 1 bed 1 bath unit located on private wooded property, steps away from 2 beaches. Private unit amenities include deck with gorgeous year round views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.