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Vacation rentals in Cape Ann

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Top-rated vacation rentals in Cape Ann

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The exterior of the 1767 Tuck House is shown, featuring a spacious two-story structure with white siding and black shutters. A welcoming teal door is framed by decorative wall sconces. Lush hydrangea bushes bloom in front, complementing the landscaped yard and stone pathway leading to the entrance.
Home in Rockport

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 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, 126 reviews
Top guest favorite
The open kitchen features a large island with seating for several guests. A cozy living area is visible, with a comfortable seating arrangement and large windows allowing natural light and ocean views. Warm wood flooring complements the airy atmosphere.
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, 173 reviews
Top guest favorite
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, 162 reviews
Guest favorite
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.

4.93 out of 5 average rating, 191 reviews
Top guest favorite
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

4.82 out of 5 average rating, 136 reviews
Top guest favorite
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 favorite
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, 226 reviews
Top guest favorite
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, 372 reviews
Guest favorite
A vibrant sunset casts warm orange and yellow hues across the ocean's surface, reflecting on gentle waves. Silhouetted rocks line the shore, while distant land appears along the horizon, creating a serene coastal scene.
Home in Rockport

Sea Vagabond - Watch the waves, stroll to the sand

"The Sea Vagabond House is an expanded 1932 summer cottage, with spectacular views of the ocean waves, with the tidal Saratoga Creek offering a mesmerizing and changing scenes from inside and outside this charming vacation home. The home sleeps eight comfortably in beds. Each level offers a full bathroom with a bathtub/shower. There are plenty of bath towels and beach towels for each guest. "Comfortable, clean and close to the beach, we will return."

4.81 out of 5 average rating, 101 reviews
Top guest favorite
A charming log cabin is surrounded by lush greenery. Two miniature horses graze leisurely on the grass in front of the cabin, which features a covered porch and simple landscaping with flowers. Sunlight filters through the trees, highlighting the serene woodland setting.
Cabin in Rockport

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

4.97 out of 5 average rating, 500 reviews
Top guest favorite
A bright entryway features a glass door that opens to a view of the water. Sunlight filters through, illuminating a welcoming space. An umbrella stand and a wicker basket are visible near the entrance, adding practicality to the design.
Apartment in Rockport

Downtown Cottage-DeckツParkingツOceanツBeachesツShopsツ

Discover coastal charm at this historic Rockport, MA gem! Breathtaking seaside views, beaches, cafes, art shops, and the Shalin Liu Performance Center nearby. Walk to iconic Motif #1, kayak, hike, or unwind at the beach. Explore nearby Salem, MA, known for its witch trials history, or take a day trip to bustling Boston, just a short drive or train ride away. Experience the best of New England coastal living. Book now!

4.99 out of 5 average rating, 114 reviews
Top guest favorite
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, 104 reviews

Popular amenities for Cape Ann vacation rentals

BeachfrontGymBBQ grillLaptop-friendly workspaceWifi

Cape Ann beach vacation rentals

Top guest favorite
A bright living area showcases large windows that offer views of the harbor. A light-colored sofa and a patterned armchair are positioned on a soft area rug, creating a comfortable seating arrangement. Natural light fills the space, highlighting the exposed beams above.
Loft in Rockport

Loft Apartment With Ocean Views

4.98 out of 5 average rating, 305 reviews
Top guest favorite
An inviting living space features a kitchenette with a stone accent wall and a modern concrete countertop. Comfortable seating is arranged beside large windows, allowing natural light to fill the area. A door leads to an outdoor space, enhancing accessibility and openness.
Apartment in Rockport

Mary's By The Sea

4.95 out of 5 average rating, 231 reviews
Top guest favorite
A comfortable living area is showcased, featuring a plush leather sofa and an armchair with a checkered pattern. Natural light streams through windows adorned with sheer curtains, illuminating the rustic wooden beams above. A wooden coffee table sits in front of the seating area, with a decorative rug beneath.
Apartment in Rockport

Harborside Retreat on Bearskin Neck

4.9 out of 5 average rating, 208 reviews
Top guest favorite
A view of a waterfront building is framed by leafy tree branches. A staircase leads to a second-floor entrance. Brightly colored kayaks are lined up along the calm water's edge, with a wooden dock visible in the background.
Condo in Rockport

Harbor Place - Airy hideaway over Rockport Harbor

4.99 out of 5 average rating, 137 reviews
Top guest favorite
Apartment in Rockport

Downtown Waterfront Escape: Views, Parking & Deck!

4.99 out of 5 average rating, 285 reviews
Guest favorite
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

4.96 out of 5 average rating, 152 reviews
Top guest favorite
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

4.98 out of 5 average rating, 387 reviews
Top guest favorite
A welcoming sign for the Rocky Neck Art Colony is displayed prominently. The sign features blue and white colors with decorative elements, including an image of a bird. Text indicates the area is one of America's oldest working art colonies, situated in historic Gloucester.
Loft in Gloucester

Rocky Neck Studio/Loft, Gloucester, Mass.

4.92 out of 5 average rating, 256 reviews

Cape Ann house rentals

Top guest favorite
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.
Home in Gloucester

Ocean views! Welcome to Sea Breeze! Winter rates!

4.98 out of 5 average rating, 112 reviews
Top guest favorite
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.
Home in Rockport

Sunny Cove Cottage, Newly Renovated!

5.0 out of 5 average rating, 108 reviews
Top guest favorite
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.
Home in Rockport

Charming waterfront home. Patio, AC, Shops, Dining

4.97 out of 5 average rating, 118 reviews
Top guest favorite
A contemporary house is set amidst lush greenery and vibrant flowers, showcasing a large yard. The exterior features large windows and a wraparound balcony on the upper level, while the surrounding garden is filled with various blooming plants.
Home in Gloucester

Gloucester Private Contemporary 4 bedrooms

4.85 out of 5 average rating, 223 reviews
Guest favorite
An outdoor deck features wooden flooring and comfortable seating arrangements, including a central coffee table. Potted red flowers add a touch of color to the space. Warm light fixtures hang above, enhancing the inviting feel of the area.
Home in Gloucester

Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem

4.98 out of 5 average rating, 103 reviews
Top guest favorite
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

5.0 out of 5 average rating, 46 reviews
Top guest favorite
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.
Home in Rockport

Oceanfront Home Rockport

5.0 out of 5 average rating, 40 reviews
Top guest favorite
An outdoor deck extends from the dwelling, featuring a dining table and chairs surrounded by greenery. In the background, wind turbines are visible beyond the landscape, enhancing the scenic coastal atmosphere.
Home in Gloucester

“Sea La Vie” 4Bed / 3Bath Walk to Good Harbor

4.95 out of 5 average rating, 44 reviews

Cape Ann cottage rentals

Top guest favorite
Cottage in Gloucester

Sunny & private cottage in Lanesville Village

4.97 out of 5 average rating, 158 reviews
Top guest favorite
A sunset over the lake creates a vibrant display of pinks and purples reflected in the calm waters. The surrounding trees frame the scene, enhancing the tranquility of the natural landscape.
Cottage in Essex

Lakefront cottage for a fun, relaxing getaway.

4.97 out of 5 average rating, 127 reviews
Top guest favorite
The cottage's exterior features a white façade with large windows, framed by greenery. A spacious deck with planters holds colorful flowers, while a barbecue grill is positioned nearby. A manicured lawn provides an inviting outdoor space, complemented by a peaceful neighborhood ambiance.
Cottage in Rockport

Life of Reilly at Back Beach

4.93 out of 5 average rating, 120 reviews
Top guest favorite
The exterior of a blue cottage is framed by vibrant green foliage and a small red maple tree. A welcoming front door is highlighted by a decorative sign. The upper balcony features black and white railings, with coordinating chairs and a playful rug at the entrance.
Cottage in Gloucester

SeaHaven Cottage at Stage Fort Park

4.86 out of 5 average rating, 189 reviews
Top guest favorite
A garden path winds through a colorful array of blooming flowers, including pink peonies and purple alliums. Green shrubs and neatly trimmed plants line the gravel walkway, which leads towards a decorative archway amidst a backdrop of lush trees.
Cottage in Essex

French Flair "Pied a Terre" Cottage on the Marsh

4.95 out of 5 average rating, 308 reviews
Top guest favorite
Cottage in Marblehead

Pool Is Open in Sept! Steps from Harbor + Old Town

4.99 out of 5 average rating, 167 reviews
Top guest favorite
A bright living room features a vaulted ceiling with exposed wooden beams. A stone fireplace is centered against a soft blue wall. Comfortable seating includes light-colored sofas and armchairs. A glass coffee table sits atop a patterned rug, with a contemporary chandelier providing overhead lighting.
Cottage in Plum Island

Sunset Bliss- stylishly renovated, 3 min to beach

4.86 out of 5 average rating, 131 reviews
Guest favorite
Cottage in Plum Island

Sunset Waterfront Retreat | Private Beach, Pool &

4.93 out of 5 average rating, 140 reviews