Holiday houses in Cape Ann

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Top-rated holiday rentals in Cape Ann

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Top Guest favourite

A cozy living area features a plush couch adorned with a throw blanket, set against a backdrop of exposed wooden beams. Stylish shelving displays decorative items, while natural light floods in through two inviting windows, complementing the warm hardwood flooring.

Home in Rockport

Walk to Shops & Beach at Historic Renovation

Are you dreaming of sun, sand and seafood? Stay at the 1767 Tuck House, where historic charm meets quintessential New England luxury! This is the perfect home for groups. Steps to the beach, shops, restaurants and arts. Home offers the privacy of boutique hotel with modern comforts: plush Casper mattresses, AC, 4K HDTV, laundry, heated floors, quartz counters, new appliances, 3BR, 3 Full Baths, 2 Kitchens, 2 Decks, Private Entries. A true Rockport gem, we promise a special stay.

4.98 out of 5 average rating, 130 reviews

Top Guest favourite

Apartment in Rockport

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.

4.99 out of 5 average rating, 175 reviews

Top Guest favourite

A cozy outdoor seating area overlooks the water, featuring two wicker chairs and a matching sofa arranged around a low table. A striped area rug anchors the space. The railing provides an unobstructed view of the rocky coastline and distant shoreline.

Apartment in Rockport

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!

4.99 out of 5 average rating, 166 reviews

Top Guest favourite

The exterior of a summer cottage is showcased, with a light grey wooden structure resting on a rocky landscape. Stairs lead up to the entrance, flanked by greenery. A deck with railings is visible on the upper level, complemented by large windows allowing natural light.

Cottage in Rockport

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

4.83 out of 5 average rating, 138 reviews

Top Guest favourite

The historic carriage house is presented in a charming turquoise color, surrounded by lush greenery and flowering plants. Tall windows provide ample natural light. A spacious yard is visible, framed by a low stone wall and iron fence.

Guesthouse in Rockport

Historic Carriage House | Dog Friendly | Hot Tub

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!

4.99 out of 5 average rating, 176 reviews

Top Guest favourite

A charming three-story house features a light yellow exterior with large windows and a pitched roof. A welcoming front porch offers a mix of outdoor seating. Lush greenery and trees surround the property, creating a serene atmosphere.

Condo in 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.

5.0 out of 5 average rating, 110 reviews

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

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!

4.99 out of 5 average rating, 228 reviews

Top Guest favourite

A bright living area features large windows with views of a garden and ample natural light. A comfortable dark sofa and a plush chair are arranged around a glass coffee table on a colorful area rug. A wooden dresser and a small dining table add warmth to the space.

Home in Rockport

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.

4.97 out of 5 average rating, 376 reviews

Top Guest favourite

A spacious deck is adorned with a round table and four chairs featuring red cushions. In the background, vibrant yellow flowers contrast against the blue ocean, with Thatcher Island's twin lighthouses visible in the distance. The scene captures a serene view of water and natural beauty.

Home in Rockport

Eden Cove

This home features spectacular views of Thatcher Island’s twin lighthouses, Loblolly Cove and the Atlantic Ocean from the spacious deck and almost every room. Downstairs there’s a fully equipped kitchen with an induction stove and a private office with views of the water. Upstairs, the master bedroom has picture windows, a king bed and an en-suite bath with walk-in shower. This quiet retreat is minutes from Town beaches and the scenic town of Rockport.

5.0 out of 5 average rating, 47 reviews

Top Guest favourite

Home in Rockport

Gather @ Ocean - Home Sleeps 14 w/ 3.5 baths

Welcome to the Gathering House - a special, spacious home - renovated in ‘21 to gather more than a dozen people – while affording pockets of peaceful rest. Enjoy the views of the ocean. Feel the sea breeze. Listen to the waves. Share meals in the gourmet kitchen or grill outdoors. Grab a beach chair & cooler and head to Loblolly Cove, Cape Hedge of Pebble Beach. This extraordinary home is ready to welcome you and your circle of love..

5.0 out of 5 average rating, 35 reviews

Top Guest favourite

The exterior of a two-story house is surrounded by lush green shrubs and blooming white daisies. A small outdoor seating area is visible, featuring two green chairs and a table set for refreshments. Natural light illuminates the inviting entrance, enhancing the welcoming appearance.

Home in Rockport

Family Friendly Home|Walk to Ocean+Downtown RKPT

KEY FEATURES: ☀️Full home with 2 levels and private yard with BBQ ☀️New AC mini split system for hot summer days ☀️Newly remodeled bathroom with walk in shower ☀️Fully equipped kitchen ☀️Washer and dryer ☀️Hi-speed WiFi ☀️Family Friendly Amenities - pack and play, high chair, toys, and more! ☀️2 parking spots ☀️Beach essentials provided in the shed- chairs, beach towels, toys and more! ☀️Board games and books

4.93 out of 5 average rating, 106 reviews

Guest favourite

The entryway features a bright, welcoming atmosphere with white paneling and natural wood accents. A staircase ascends to the upper level, while a door with a frosted window leads outside. A round mirror hangs above a striped rug, enhancing the space's inviting feel.

Apartment in Rockport

Ocean View unit with Private Roofdeck in Rockport

Enjoy beautiful ocean views from Bearskin Neck! This cute and cozy 1-2 bedroom unit has been completely renovated. Nice bright colors and sea decor thoughout. Downtown Bearskin Neck location offers beaches, harbors, kayaking, ocean breezes and fresh seafood - all steps from your door! Unit has private roofdeck with astonishing views. Enjoy relaxing on the roofdeck with a glass of wine while watching the sunset!

4.82 out of 5 average rating, 149 reviews