House holiday rentals in Rockport

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.

4.96 out of 5 average rating, 81 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.

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, 145 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 welcoming living area features a comfortable gray sofa paired with a vibrant blue armchair. Natural light fills the space through multiple windows, highlighting the wooden ceiling beams. A dining table with two chairs sits nearby, complemented by decorative art and an accent rug.

4.98 out of 5 average rating, 104 reviews

Walk to Beach/Town at Historic Renovation

Come visit a very special home this winter! 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 TV, 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.

4.93 out of 5 average rating, 171 reviews

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.

Home in Gloucester

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.

4.97 out of 5 average rating, 143 reviews

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.

Home in Gloucester

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).

4.98 out of 5 average rating, 328 reviews

A cozy living room features a white-brick fireplace, with a functional gas flame. Stylish furniture includes a patterned armchair and a soft couch, complemented by a light-colored striped wooden floor. Large windows allow natural light and offer views of the surrounding area.

Home in Rye

*Beachfront* Vintage Coastal Cottage - Relaxation

It's always about the view and this place will leave you feeling energized and calm. Situated on premium beachfront property, this single family home has luxurious amenities like super plush towels, organic cotton bedding and touches to make your getaway feel that much Take a virtual tour here: https://bit.ly/3vK5F0G We've outfitted it with an extra screen and a setup to get you up and running. Google home and Sonos systems bring this 100 year old beauty into this century.

5 out of 5 average rating, 160 reviews

A welcoming living area showcases a large screen displaying Netflix. Two brown armchairs with throw pillows are positioned beside a modern coffee table. A cozy fireplace adds warmth, while soft gray and blue tones create a relaxing atmosphere. Natural light filters through the windows.

Home in Kittery Point

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away!

4.92 out of 5 average rating, 134 reviews

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.

Home in Gloucester

Gloucester Beach House, near Good Harbor Beach!

Escape to this inviting, and pup friendly 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. Openings for September and October. Ideal for weekend get aways!

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.

4.97 out of 5 average rating, 346 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.

4.96 out of 5 average rating, 160 reviews

A dining area is showcased with a rustic wooden table surrounded by four chairs and a bench. An arrangement of circular placemats lies on the table. Natural light enters through a window, illuminating the wooden floor and a potted plant sits on the table.

Home in Salem

Beautiful historical house in Salem

The whole group will enjoy easy access to everything from this centrally located place. A few minutes walk to a multitude of great restaurants, shops, galleries, the witch house, ghost and witch tours, trolley tours, Salem ferry, Pickering wharf, Salem witch museum, witch dungeon museum and a few minutes drive to Salem Willows and the house of the seven gables. All three bedrooms that are on the second floor will have AC units from mid June till September.

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.

4.96 out of 5 average rating, 90 reviews

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.