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Vacation rentals in Gloucester

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Top-rated vacation rentals in Gloucester

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French doors open into a cozy living area where a sectional sofa is visible. A small green table with a bouquet of flowers sits in front, while sunlight illuminates the space. Outside, garden views reveal lounge chairs and vibrant flowers.

Guesthouse in Annisquam

4.96 out of 5 average rating, 273 reviews

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

An expansive view of the ocean showcases rolling waves under a partially cloudy sky. A deck is visible, outfitted with outdoor seating, surrounded by lush greenery and coastal vegetation, creating a serene outdoor space.

Apartment in Magnolia

4.86 out of 5 average rating, 122 reviews

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

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

4.93 out of 5 average rating, 161 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.

Home in Gloucester

4.97 out of 5 average rating, 130 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 modern living area features a light-colored sofa adorned with decorative pillows and a natural wooden coffee table. A round mirror reflects light, while a small wooden side table and a potted plant add a touch of greenery. Soft ambient lighting enhances the soothing atmosphere.

Apartment in Gloucester

4.96 out of 5 average rating, 124 reviews

Beautifully remodeled unit in heart of Gloucester

Enjoy your stay in the heart of Gloucester close to everything this great town has to offer. This unit was completely remodeled in 2022. Two shorts blocks from Main Street in Gloucester and all of its wonderful restaurants and shops. Three blocks from the Beauport Hotel - perfect for wedding guests not staying at that location. This unit has new floors, countertops, appliances and fixtures and is freshly painted (no VOC paint). You will love this unit and location for your visit.

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

4.91 out of 5 average rating, 207 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2025! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

Top guest favorite

A spacious game room features a stylish hanging chair and a classic arcade machine in the background. Natural light illuminates the wood-paneled ceiling and bright walls, creating a welcoming space ideal for family fun or relaxation.

Condo in Gloucester

4.99 out of 5 average rating, 116 reviews

3BR Oceanfront Condo with decks

Have fun with the whole family at our stylish oceanfront condo. Capture exquisite sunrises and sunsets off of the decks overlooking the ocean. Spend time in the spacious arcade/game room with family and friends or listen to some smooth beats using our retro record player. Walk to downtown Gloucester where you will find a number of restaurants and bars or alternatively walk to exquisite beaches or parks all available steps from your front door.

A cozy outdoor deck is presented with natural wood planks, leading to sliding glass doors framed by blue siding. Potted plants and decorative items are positioned near the entrance. A nearby patio chair adds to the inviting setting surrounded by landscaped greenery.

Condo in Gloucester

4.95 out of 5 average rating, 117 reviews

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

An open-concept living area is highlighted by a modern kitchen featuring a large island with seating for four. A spacious seating area with a blue couch complements the dining space, while a sliding door leads to an outdoor patio. Ample lighting enhances the contemporary design.

Apartment in Gloucester

4.86 out of 5 average rating, 105 reviews

Long Beach Suites: Steps Away From Surf!

Recently built, Long Beach Suites is ready to welcome you this summer. With peaks of Long Beach, come stay in one of our two bedroom apartment suites. Expertly built with summer visitors in mind. Long Beach Suites is just steps away from Long Beach in Rockport and only ten minutes to Good Harbor. You will be staying one of four similar apartments, photos may not be of exact unit.

The exterior entrance features a charming black door beneath an elegant archway. Flanked by decorative planters and surrounded by thoughtfully trimmed greenery, the light blue siding of the building presents a welcoming appeal. The name 'GILBERT' is displayed prominently above the entrance.

Apartment in Gloucester

4.97 out of 5 average rating, 152 reviews

The Gilbert: 1-Bed downtown suite, walk to beach.

Come stay in Gloucester’s historic downtown district, in St. Peter’s Square, just one block from Pavilion Beach, Stacey Boulevard and the historic West End of Main Street. The Gilbert sleeps two (up to 3 with an air mattress). A perfect getaway for those in love with history and seaside living. The unit has a private entrance, king sized bed, kitchenette and private bath.

Top guest favorite

A charming garden area surrounds the cottage, featuring vibrant flowers and greenery. A white picket fence defines the space, while two blue shutters flank the windows. A small stone feature adds interest, and a soft gravel path leads up to the entrance.

Cottage in Gloucester

4.97 out of 5 average rating, 138 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Now with mini-split A/C and new windows in the bedrooms! Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

A cozy living area is highlighted by a dark green sofa and a large screen displaying a streaming service. The modern kitchen features stainless steel appliances and countertops, while a stylish patio offers outdoor seating surrounded by lush greenery.

Loft in Gloucester

4.97 out of 5 average rating, 176 reviews

Downtown, Shops, Beach, Deck, Close to Salem

Escape to the charming heart of Gloucester with this quaint and comfortable one-bedroom retreat, perfect for couples seeking for a rejuvenating getaway. Nestled in the heart of downtown, this enchanting home boasts a prime location just moments from the city's finest restaurants, shops, and attractions.

Vacation rentals for every style

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Popular amenities for Gloucester vacation rentals

Laptop-friendly workspace

Stay near Gloucester's top sights

Wingaersheek Beach36 locals recommend

Crane Beach124 locals recommend

Halibut Point State Park37 locals recommend

Gloucester beach vacation rentals

Top guest favorite

A cozy living room features large windows that invite natural light, accented by a ceiling fan. Comfortable brown leather seating surrounds a dark coffee table, which holds magazines. A light-colored area rug complements the space, while a wall-mounted shelf displays decorative items.

Apartment in Salem

5 out of 5 average rating, 133 reviews

2-Bedroom Ocean View Walk to Beach and Downtown

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

4.95 out of 5 average rating, 187 reviews

Mary's By The Sea

A light-filled living area features a pull-out sofa adorned with striped cushions and a coffee table with a decorative book and lamp. A sliding glass door opens to a sleeping area with a spacious bed, while bright curtains frame the window, offering a view of the exterior.

Guest suite in Lakeside Marblehead

4.91 out of 5 average rating, 277 reviews

Ocean Park Retreat

Top guest favorite

A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.

Apartment in Winthrop

4.96 out of 5 average rating, 252 reviews

Oceanfront Pool. Close to Boston. Free Parking.

Top guest favorite

A serene view through a window shows a group of ducks swimming in calm water. A small sailboat decoration is positioned at the bottom corner of the window, complementing the tranquil setting.

Guest suite in Rockport

4.97 out of 5 average rating, 114 reviews

8 Bells by the Sea - Private Suite-On the Beach!

Top guest favorite

A serene lakeside view captures a vibrant sunset with the sun partially descending behind distant hills. A lone fisherman in a boat is visible on the water, while a wooden deck features seating arrangements surrounded by lush plants.

Guest suite in Tyngsborough

4.98 out of 5 average rating, 255 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Top guest favorite

A serene winter landscape stretches across the view, showcasing a vibrant sunset reflected over a tranquil water surface. Snow covers the ground, while a shoreline with rocky formations is visible, framed by bare trees against the colorful sky.

Place to stay in Salem

4.96 out of 5 average rating, 247 reviews

Seadrift Inn - 2 bedroom 2nd floor apt by the sea!

A spacious living area features a comfortable sectional sofa with patterned upholstery, situated alongside large windows offering expansive views of the waterfront. Natural light floods the room, complemented by warm wooden accents on the ceiling and floor. A dining table for four is placed near the windows.

Cottage in Newburyport

4.93 out of 5 average rating, 121 reviews

Sunset Waterfront Privacy Beach

Gloucester house rentals

Top guest favorite

A well-lit bedroom features large windows with scenic water views. A spacious bed is dressed in soft linens, accompanied by a cozy throw. A small seating area includes two chairs and a lamp, enhancing the relaxing atmosphere of the room.

Home in Ipswich

4.97 out of 5 average rating, 109 reviews

Hillside

Aerial view of the spacious home reveals a wraparound deck with multiple seating areas, including shaded tables beneath umbrellas. The exterior features a light yellow façade complemented by large windows, surrounded by greenery that enhances the property's serene, secluded ambiance.

Home in Gloucester

4.93 out of 5 average rating, 109 reviews

Aerie, 2 king beds, large space, AC, 2 beaches!

A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.

4.94 out of 5 average rating, 159 reviews

Quaint Little New Hampshire Lake House Getaway!

Top guest favorite

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.

Home in Gloucester

4.99 out of 5 average rating, 201 reviews

Rocky Neck Retreat

A serene sunset is captured over the horizon, casting warm hues of orange and pink across the sky. The silhouette of a distant landscape is visible along with the calm waters reflecting the evening light.

Home in Ipswich

4.88 out of 5 average rating, 101 reviews

Incredible Views of Ocean, River, Sunrise & Sunset

Top guest favorite

A fire pit is surrounded by colorful adirondack chairs in a grassy area, with bright yellow flowers adding a pop of color. The view in the background includes a landscape of greenery leading to the water, suggesting a peaceful outdoor space for gatherings.

Home in Ipswich

4.99 out of 5 average rating, 202 reviews

Stagehill Beach House

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

4.83 out of 5 average rating, 195 reviews

Gloucester Private Contemporary 4 bedrooms

Top guest favorite

Home in Rockport

4.97 out of 5 average rating, 337 reviews

Charming Toe-Hold, A Short Walk to Town and Beach

Beach house rentals in Gloucester

Top guest favorite

The exterior of the cottage is visible, featuring light gray siding and multiple windows with white trim. A vibrant display of pink flowers is situated in the foreground, providing a colorful contrast to the structure.

Home in Hampton Beach

4.96 out of 5 average rating, 285 reviews

2 Bedroom Beach Bungalow, Steps from the Beach!

A view through the window showcases the ocean and beach, framed by a stone column and a decorative railing. Comfortable seating in teal decor is visible, inviting relaxation while enjoying the coastal scenery.

Home in Salisbury

4.88 out of 5 average rating, 222 reviews

Spacious waterfront free parking &Wi-fi

Home in Annisquam

4.94 out of 5 average rating, 34 reviews

Private Beach!

Home in Rockport

4.85 out of 5 average rating, 48 reviews

4BR Oceanfront Rockport Vacation on Long Beach!

A serene view of a calm river, reflecting the warm light of sunrise. A bridge spans the water, with a rainbow faintly visible in the sky. A wooden dock extends towards the water, bordered by trees and boats moored nearby.

Home in Kittery

4.94 out of 5 average rating, 145 reviews

Gorgeous Waterfront Home with Dock and Beach

Top guest favorite

An aerial view captures several charming homes nestled along a lush green waterfront. A private dock extends into the water, surrounded by rocks and greenery. The scene conveys a serene landscape, blending nature and cozy residences complemented by gentle water reflections.

Home in Gloucester

5 out of 5 average rating, 12 reviews

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

Top guest favorite

The exterior of the home is captured under cloudy skies, displaying a two-story structure with navy blue siding and white trim. Stairs lead to an upper deck, while a small landscaped area is visible at the base. Snow covers the ground, adding to the serene ambiance.

Home in Weymouth

4.94 out of 5 average rating, 129 reviews

Newly remodeled home with ocean views!

The serene lake is framed by trees, reflecting the soft colors of the sunset sky. Gentle ripples disturb the water's surface, creating a tranquil atmosphere. In the distance, the silhouettes of trees and properties are visible along the shore, enhancing the peaceful landscape.

4.83 out of 5 average rating, 138 reviews

Beautiful Lakefront Vacation

Quick stats about vacation rentals in Gloucester

Total rentals
610 properties
Total number of reviews
27K reviews
Family-friendly rentals
390 properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
280 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Gloucester?
Make yourself at home in Gloucester by choosing from our most frequently booked neighborhoods. We have over 260 vacation rentals in Riverview, over 260 vacation rentals in West Gloucester, and over 340 vacation rentals in Annisquam.
Are there vacation rentals with a dedicated workspace in Gloucester?
Yes! Work meets play with ease at over 280 vacation rentals in Gloucester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Gloucester?
Four-legged friends are welcome in Gloucester. Choose from more than 170 vacation rentals for guests traveling with pets.
Are there Gloucester vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Gloucester, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in hotel rentals in Gloucester?
Experience the best of Gloucester with our hotel rentals, starting at about $350 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Gloucester have a gym?
Absolutely! We offer over 10 house rentals with a gym in Gloucester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gloucester have self check-in?
Absolutely! We offer over 90 house rentals with self check-in in Gloucester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gloucester have a bbq area?
Absolutely! We offer over 110 house rentals with a bbq area in Gloucester. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Gloucester?
Gloucester has more than 260 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Gloucester?
Enhance your stay in our House Rentals with the most popular amenities: over 110 homes with a bbq area, over 90 homes with self check-in, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore