Holiday houses in Rockport

Captains Quarters- 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

Harbor Retreat | Ocean View | Heart of Downtown

Discover Rockport's Harbor View Apartment! 🌊 This newly renovated 1-bedroom on the second level boasts stunning harbor views from a private deck. Steps from Bearskin Neck, enjoy proximity to unique shops 🛍️, fine dining 🍽️, and beaches 🏖️. Equipped with high-speed WiFi, a 55" Smart TV, and a Murphy couch. Perfect for experiencing Rockport's vibrant atmosphere. Note: Guests must climb stairs and the downtown location can be lively and noisy 🌆. Book your unforgettable seaside escape today! ⚓

3 Bedroom Apartment with parking on Bearskin Neck

Built in 1822, the Sound House is conveniently located on Bearskin Neck. The upstairs apartment is renovated with brand new oak floors, new bathrooms, and updated living area. The unit features 3 bedrooms and 2 full bathrooms, with laundry as well as 3 parking spaces in the back of the building. The kitchen includes cooking utensils, with an electric grill and butane burner for outdoor cooking on the new deck overlooking Cape Ann. Enjoy Rockport while creating new memories at the Sound House!

Mary's By The Sea

A unique 650 square foot ground floor apt across the street from Front Beach. 6 minute walk from the Rockport MBTA . There is a separate bedroom with a queen mattress and a pullout sofa bed in the living area. The pullout sofa is best for teens or smaller kids . There is a bathroom with a sink and toilet. There is another room with a sink and shower. The kitchen area is more like a kitchenette than a full-size kitchen. We provide one parking spot next door at The Cove parking lot.

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!

Downtown Rockport|King Bed w/Parking|Walk to Train

Inquire about our winter rental rates! • Newly remodeled and professionally furnished space! • Steps to Beaches, Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu • Private off street parking spot for 2 cars • High Speed Wi-Fi and AC • 10 minute walk from commuter rail to Boston • Smart TV equipped to stream all your favorites • Fully stocked and renovated kitchen • Comfortable KING size memory foam bed • Convenient EV charging right across the street!

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!

Rockport Getaway near ocean, music hall & downtown

This private, newly-renovated, well-appointed entire two-bedroom garden apartment comfortably sleeps four with full kitchen, bathroom, washer/dryer, central A/C. Desirably located, just steps to Rockport Harbor, restaurants, shopping, Shalin Liu Performance Center and short walk to beaches. Free onsite parking for two cars. Exclusive side yard use with patio, outdoor furniture and table. Bright & airy, it's a quiet, restorative getaway. Available for longer winter rental too.

Fall Asleep to Waves — Steps to Shops & Dining

• Ocean-view bedroom • Steps to Front Beach • Walk to Bearskin Neck • Pet friendly •15-min walk to commuter rail • Contemporary art gallery downstairs Cozy one-bedroom apartment ideally located in downtown Rockport, with a peaceful harbor view from the bedroom. Guests enjoy direct, private seasonal access to Front Beach via a staircase on the property. This is one of three private guest apartments at The Pearl, located just behind Thalassa, our contemporary art gallery.

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.

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.