House vacation rentals in Rockport

4.96 out of 5 average rating, 134 reviews

A spacious living area features large windows overlooking the water. A gray sofa and a blue armchair provide comfortable seating, while a wooden coffee table sits in front. A dining table with white chairs is positioned nearby, creating an inviting space for relaxation and meals.

Home in Annisquam

Views over Lobster Cove! Book spring weekends

Booking summer and fall 2025. Water views/access, sunsets above Lobster Cove on Washington St. Ideal for couple, NEW KING BED in master, queen in 2nd. Fast WiFi./TV. Not suitable for young children. Central A/C. 2nd fl unit large windows. Large living/dining/kitchen area. Comfy new mattresses, 100% cotton sheets,sound machines. Overlooks beautiful Lobster Cove and footbridge. Minutes walk to the village of Annisquam and Lighthouse Beach. Small deck. Swim/kayak out your door. Parking for one car

Two white rocking chairs sit invitingly along a stone walkway, facing a calm harbor. Reflections of colorful buildings and boats can be seen on the water's surface, framed by a vibrant sky during sunset.

4.95 out of 5 average rating, 57 reviews

Charming waterfront home. Patio, AC, Shops, Dining

Discover your dream Rockport getaway! You'll stay nestled on Bearskin Neck, in this cozy harborside condo boasting stunning views, steps from shops, beaches, & galleries. Relax on your private patio overlooking the iconic Motif #1 for your morning coffee or evening happy hour. Book now for a fun getaway, year-round! There is one bedroom upstairs and a pullout sofa downstairs that can sleep 2. We welcome pets, but ask that they remain off furniture and out of the bed. A pet fee will auto-apply.

The image features a serene marina scene under a clear blue sky, with various boats docked along the water. Towering trees and greenery frame the view, while the gentle architecture of nearby buildings adds to the coastal landscape.

4.99 out of 5 average rating, 197 reviews

Rocky Neck Retreat

.Relaxing private location .4 beds 2 baths with full kitchen/pans/Dishwasher/Wash/Dryer.Renovated organic design integrates historic architecture with modern touches.If you come for hikes, beach/music/food scene, you will enjoy the Rocky Neck District .The unique home has 4 bedrooms /4 Queen Beds. Speedy WIFI .Parking is up a steep narrow drive . NO trucks or Large SUVs. 2 cars max. Note* Kitchen and LR are upstairs.There are stairs. Contact owner for questions re:parking or limited mobility.

A two-story home features a light gray exterior with white trim and a front porch. A cobblestone driveway is visible in front, surrounded by a well-maintained yard with green shrubs. The property is situated within a peaceful neighborhood setting.

5 out of 5 average rating, 45 reviews

New South End Home Quiet Lane To Old Garden Beach

Newer furnished home, 1/2 mile walk to quaint Bearskin Neck with Rockport shops & galleries. Old Garden Beach 1/4 mile walk down a quiet unpaved lane. 3 BR/3 Bath home available for summer weekly vacations. Family friendly, 3 prkg spaces, 2 decks, new appliances (laundry, microwave & dishwasher), hardwood floors, new rugs & beds, full basement w/ pool table, fenced yard. Several beaches, hiking trails nearby or take a train to Salem, Newburyport, or Boston. Longer term winter rental available

Home in Lakeside Marblehead

The living area features a dark blue sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front, surrounded by natural light from nearby windows. The white walls and sleek countertops contribute to a modern, open space. A minisplit unit is visible for climate control.

5 out of 5 average rating, 129 reviews

Seaside Cottage

Here you are down the street from some of Marblehead's hidden gems such as Redds Pond, Browns Island & Old Burial Hill Cemetery. One car parking. 5 minute walk to the beach, shops & restaurants. Fully fenced in yard with turf grass. One bedroom with a low profile queen sized bed. In unit washer/dryer. Full bath with tub. Newly renovated kitchen with major appliances: stove, oven, dishwasher, fridge, Nespresso maker & microwave. Sheets & bath linens provided. Minisplit A/C. Home is all one level.

A charming exterior view of a renovated home features a welcoming orange door at the entrance. A spacious covered porch is lined with white railings, complemented by lush landscaping, including purple flowers and greenery. A brick pathway leads to the front steps.

5 out of 5 average rating, 10 reviews

Whale Cove Waterview

Renovated (2023) South End home with sun-filled rooms: many with ocean views. Large kitchen with seating for 6 at island and fully equipped. Comfortable family room with flat screen tv and gas fireplace. Primary suite with queen bed and bath with double sinks and walk-in shower. Remaining two bedrooms share a bathroom with walk-in shower or a 1st floor full bath with tub. Mudroom with washer and dryer. Second floor deck to enjoy a view of Whale Cove; ground level patio with Weber grill.

A serene waterfront view captures gentle waves reflecting the soft hues of a sunset. Two sailboats float peacefully in the water, while a rocky shoreline and a stone breakwater are visible in the distance.

4.96 out of 5 average rating, 28 reviews

The Fort Hideaway- top of Bearskin Neck

Enjoy a memorable stay at The Fort, a historic landmark atop Bearskin Neck. Experience the bustle of Bearskin neck with its shops, galleries and eateries while having a peaceful waterfront oasis stay. This rarely available space is on the lower level of a charming house with light and glorious water views at every angle... A cooks kitchen enhances this two bedroom unit, with an adjoining dining room and a living room. Enjoy an outside stone patio with dining and seating by the waters edge…

A charming white house is positioned along a rocky shore, showcasing a four-season porch with large windows that provide views of the harbor. Lush greenery surrounds the property, complementing the tranquil water scene with boats in the distance.

4.93 out of 5 average rating, 156 reviews

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.

The exterior view of the home reveals a modern wooden structure surrounded by lush greenery. A spacious deck extends from one side, while stone pathways weave through well-maintained gardens. Soft blue skies and gentle clouds create a serene atmosphere.

4.98 out of 5 average rating, 124 reviews

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

A charming cape house is viewed from the street, featuring a covered porch with white railings. Large windows allow natural light to fill the interior. The surrounding yard is flat and grassy, bordered by trees that provide shade in a peaceful neighborhood.

4.91 out of 5 average rating, 129 reviews

Gloucester Beach House, near Good Harbor Beach!

Make your July escape to this inviting 4-bedroom Gloucester home, just a short walk to Good Harbor Beach! This classic coastal home blends comfort & convenience. All 4 bedrooms are air-conditioned, featuring a large eat-in kitchen, covered front porch perfect for relaxing or grilling, full bathroom plus refreshing outdoor shower. Stay connected with high-speed Wi-Fi, & enjoy the ease of on-site laundry. 📅 Weekly rentals available only for early July—book now before it’s gone!

4.97 out of 5 average rating, 331 reviews

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.

A cozy family room is filled with natural light from multiple large windows, offering views of the outside. A comfortable gray sofa and two white chairs are arranged around a glass coffee table. Decorative pillows and a fresh flower arrangement enhance the inviting setting.