House holiday rentals in Rockport

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.

4.98 out of 5 average rating, 122 reviews

Walk to Beach & Shops 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 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.

ValueFamilyParks

A welcoming outdoor patio features white lounge chairs arranged around a flower-filled planter. A brick chimney adds to the charm of the cottage, which is complemented by large windows showcasing ocean views. Lush greenery is situated alongside the patio.

4.96 out of 5 average rating, 24 reviews

Cottage at Back Beach

Ocean Views in this Charming 2 bedroom Cottage. The property has a wonderful open kitchen and dining room that gives way to an ocean facing patio. Great views from this Back Beach Cottage. Two bedrooms, one with en-suite bathroom, the other with two single beds. Wonderful location - directly across the street from the Back Beach, a 5 minute walk to downtown Rockport, and the Shalin Liu performing arts center, galleries and coffee shops. This is the front cottage of a two cottage property.

LocationFamilyView

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.

4.94 out of 5 average rating, 53 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…

FamilyLocationCondition

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, 190 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.

FamilyValueBathroom

5.0 out of 5 average rating, 20 reviews

The Rockport Retreat-walk to beaches and downtown

Enjoy the sights and charm of Rockport from this inviting home, perfectly located just a few blocks from downtown shopping, restaurants, galleries, and sandy beaches. With plenty of room for family and friends, this property offers a fresh, comfortable interior and an ideal blend of convenience and relaxation with plenty of space for everyone to gather or unwind. Front Beach and Rockport's center are about 0.7 miles away. Commuter rail to Boston/Salem is about 0.5 miles away.

FamilyLocationCleanliness

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, 366 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.

FamilyValueDecor

4.97 out of 5 average rating, 34 reviews

Historic Oceanfront Home - Walk to Downtown

Escape to the charm of Rockport, MA in this historic, light-filled, 4 bedroom, 1 1/2 bath well equipped home located across the street from Back Beach and just a short stroll from Bearskin Neck and the picturesque harbor. Enjoy breathtaking ocean views from nearly every room in the house. Whether you're here for a romantic weekend, a family vacation, or a peaceful retreat, this inviting space offers the perfect base to experience all the beauty of Cape Ann.

ValueFamilyKitchen

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.

4.97 out of 5 average rating, 124 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.

LocationValueDecor

A panoramic view reveals the tranquil ocean, with soft waves lapping against the shore. Green trees and distant sandy areas are visible, enhancing the natural scenery. Several rooftops in the foreground provide a sense of elevation and perspective towards the coastline.

4.98 out of 5 average rating, 109 reviews

Ocean views! Welcome to Sea Breeze! Winter rates!

Sea Breeze offers a spacious, newly renovated, 4 bedroom escape, that smiles down upon Good Harbor beach. Take in the refreshing salt air breezes while enjoying the solitude of being situated at the end of a quiet cul de sac. A short 3-5 minute drive gets you into the Good Harbor parking lot or take a 20 minute walk instead. Close-by downtown Gloucester is teeming with spectacular restaurants and activities for the whole family.

ValueLocationAccuracy

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.

4.93 out of 5 average rating, 101 reviews

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

LocationFamilySolo travel

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, 112 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.

ValueFamilyKitchen

A front porch is showcased with two wooden chairs positioned on a deck of brown planks. Sunlight filters through surrounding trees, and a view of the street is visible through the open entryway. The overall setting offers a serene outdoor space for relaxation.

5.0 out of 5 average rating, 107 reviews

Sunny Cove Cottage, Newly Renovated!

Newly renovated cottage in Pigeon Cove with tons of sunlight and only steps from the sea! Sit on the front porch with your cup of coffee or your glass of wine and enjoy the quiet neighborhood and the salty breeze. Located 2.5 miles from Bearskin Neck and 1.6 miles from Front Beach!

LocationValueGetting around

Popular amenities for Rockport house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 182 reviews

A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.

Home in North Andover

Nana-tucket Inn

FamilyValueLayout

5.0 out of 5 average rating, 23 reviews

A spacious outdoor area features a heated pool surrounded by a paved patio. White lounge chairs and a dining table are positioned nearby, offering ample seating. A large umbrella provides shade, while a well-maintained lawn and wooden fence create a private retreat.

Home in Essex

Heated Pool Firepit Huge Screen Porch King bed

LocationFamilyHeating

A clear blue swimming pool is framed by a spacious wooden deck, featuring several lounge chairs and a large umbrella for shade. Lush greenery surrounds the area, creating a secluded atmosphere. The inviting water reflects the bright blue sky overhead.

4.95 out of 5 average rating, 21 reviews

Twin Shores Poolside Haven

ValueFamilyWalkability

5.0 out of 5 average rating, 16 reviews

Home in Chelsea

Theatre | Arcade | Pool w. Free 3 Car Parking

FamilyLocationAccess

5.0 out of 5 average rating, 9 reviews

Home in Methuen

The Stunning Melita Farms Geodesic Dome Farmhouse

LocationFamilyHospitality

4.99 out of 5 average rating, 71 reviews

An indoor pool is surrounded by light blue walls and gray tile accents. Natural light filters in through large windows, illuminating the water's surface. Steps lead from the pool to a door that opens to the outside area.

Home in Hampton

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

FamilyLocationAccess

4.93 out of 5 average rating, 15 reviews

A spacious living area features a classic red-brick fireplace as a focal point. Dark leather seating is arranged around a central coffee table, while a patterned area rug adds texture to the hardwood floor. Light from overhead fixtures illuminates the room.

Home in Hampton Beach

Ocean Breeze Hideaway

FamilyLocationNearby

5.0 out of 5 average rating, 39 reviews

Home in Newton

Spacious quiet Newton Villa *Easy Boston Access!

FamilyLocationAccuracy

Weekly house rentals

An aerial view captures the beautiful curves of Long Beach, framed by gentle waves lapping the sandy shore. Coastal homes line the beach, blending with the lush greenery in the background. The azure ocean extends into the distance, reflecting the serene sky above.

5.0 out of 5 average rating, 39 reviews

Oceanfront Home Rockport

LocationValueCleanliness

The living room features comfortable seating arranged around a round coffee table. Large sliding doors provide access to a waterfront view, while natural light illuminates the space. A smart TV is mounted on the wall, and a mirrored wall adds depth to the open-concept area.

4.97 out of 5 average rating, 29 reviews

Waterfront Rockport Gem Steps to Shops and Beaches

FamilyLocationLayout

An airy living room features a high, wooden-beamed ceiling, enhancing the spaciousness. Large windows allow natural light to fill the area, where two armchairs and a gray sectional couch provide comfortable seating. A woven basket and a small blue table add functional details.

4.97 out of 5 average rating, 37 reviews

Seaside Cottage steps from the Beach & Downtown

FamilyLocationView

A cozy living area is defined by wooden beams and a colorful area rug. A comfortable sofa and an armchair provide seating, while a small table and a trunk add character. Soft lighting from table lamps brightens the space, and a television is mounted on the wall.

4.97 out of 5 average rating, 70 reviews

Historic gem in seaside village

LocationFamilyComfort

The kitchen features modern stainless steel appliances and a spacious countertop. Several barstools are arranged around the island, while a round dining table with wooden chairs is visible in the corner. Bright natural light fills the space through multiple windows.

4.91 out of 5 average rating, 43 reviews

Walk to Town, Beach & Train to Salem - AC, Pets OK

LocationFamilyWalkability

5.0 out of 5 average rating, 11 reviews

Little Pearl Cottage

FamilyLocationDecor

A screened-in porch features a comfortable seating arrangement, with a black wicker sofa and red cushions. Potted ferns and a decorative nest adorn the walls. Natural light filters through the lattice, and a patterned rug adds a touch of color to the space.

4.9 out of 5 average rating, 67 reviews

A Breezy Cottage at Back Beach

LocationFamilyIndoor spaces

A historic Colonial home is depicted with dark wooden siding and multiple windows. The structure features a central door, surrounded by evenly spaced windows on the front facade. Trees and greenery are visible in the surrounding yard, under a bright blue sky.

5.0 out of 5 average rating, 31 reviews

William Haskell House First Period Colonial Home

FamilyLocationComfort

Private house rentals

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and oven. White cabinetry offers ample storage, while a large window allows natural light to illuminate the countertop. A sink is positioned near the window, enhancing functionality in the space.

4.98 out of 5 average rating, 41 reviews

Walk to Old Garden Beach! 3 Bedroom Home!

FamilyLocationOutdoor spaces

A spacious two-story home is shown, featuring a classic facade with white siding and dark shutters. A well-maintained yard includes a flowering tree and landscaped stone beds. A large driveway leads to an attached garage, while the surrounding area is marked by trees and greenery.

4.98 out of 5 average rating, 56 reviews

Rockport ~ Entire 3000 Square Foot Relaxing Home!

ValueLocationKitchen

An aerial view showcases a large three-story house with a classic New England design, surrounded by lush greenery. The property is situated near the coastline with views of the ocean, featuring manicured lawns and pathways leading to outdoor living spaces.

4.98 out of 5 average rating, 54 reviews

Classic New England: Big Family Home; Spas|Garden

LocationFamilyGetting around

A wooden dock extends into calm waters, reflecting the vibrant colors of the sunset. Surrounding marshlands are visible in the distance, while gentle clouds drift across the sky. The scene evokes a sense of serenity and connection to nature.

4.95 out of 5 average rating, 44 reviews

Evensong: Lovely Oceanview Retreat with Dock

LocationFamilyHeating

5.0 out of 5 average rating, 8 reviews

Sunset Serenity-Entire Cozy Home-30 min to Salem

LocationWalkabilityIndoor spaces

4.87 out of 5 average rating, 90 reviews

Walk to Plum Cove Beach 2BR/2BA Coastal Retreat

FamilyValueBathroom

A bright living area features a brown leather sofa complemented by a decorative blanket. Natural light enters through large windows adorned with soft curtains. A minimalistic bookshelf is filled with decorative items, while a potted plant adds a touch of greenery to the space.

4.97 out of 5 average rating, 88 reviews

The Essex of Gloucester

FamilyValueBeach

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.