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Vacation rentals in Gloucester

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Gloucester vacation rentals

Beachfront
Self check-in
Gym
BBQ grill
Laptop-friendly workspace

Stay near Gloucester's top sights

Wingaersheek Beach104 locals recommend
Crane Beach124 locals recommend
Good Harbor Beach120 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, 139 reviews

2-Bedroom Ocean View Walk to Beach and Downtown

Superhost
A spacious window with dual openings frames a view of the ocean and sandy beach across the street. The interior walls are painted in a calming blue, complementing the natural light that fills the room. Grassy areas can be seen in the foreground.
Apartment in Nahant
4.97 out of 5 average rating, 101 reviews

The Blue Pearl

Superhost
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
4.9 out of 5 average rating, 281 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, 254 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, 118 reviews

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

Guest favorite
A charming Victorian-style house is set against a cloudy sky, showcasing its historic architecture. Lush greenery surrounds the property, with a well-maintained stone wall visible in the foreground. Several parking spaces are also noticeable, enhancing the accessibility of the location.
Guest suite in Hull
4.95 out of 5 average rating, 152 reviews

BOSTONS BEST BED & BEACH1- HULL, MA

Guest favorite
A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.
Apartment in Arlington
4.98 out of 5 average rating, 202 reviews

Lakeside apartment, patio, hot tub, outside shower

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, 252 reviews

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

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Gloucester house rentals

Superhost
The exterior of a two-story house features a light grey siding with white trim. Large windows are visible on the front, providing natural light to the interior. A stone pathway leads to the front door, surrounded by greenery and flower beds.
Home in Gloucester
4.76 out of 5 average rating, 160 reviews

Gloucester getaway ocean escape

Guest favorite
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, 110 reviews

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

Top guest favorite
A modern living area features vaulted ceilings and wooden accents, creating an open atmosphere. A large flat-screen television is mounted on a white media console. Comfortable seating is provided on a dark sectional sofa, complemented by natural light from skylights and windows.
Home in Newburyport
4.99 out of 5 average rating, 155 reviews

“Salty Girl” Plum Island, MA

Guest favorite
A modern kitchen is highlighted by a large central island with seating for four. White cabinetry contrasts with a tiled backsplash in soft green tones. A sleek range hood is positioned above a gas cooktop, while steps lead to the upper level to the right.
Home in Gloucester
4.98 out of 5 average rating, 45 reviews

Harbor House with Ocean Views

Guest favorite
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
4.89 out of 5 average rating, 105 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, 205 reviews

Stagehill Beach House

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
4.83 out of 5 average rating, 199 reviews

Gloucester Private Contemporary 4 bedrooms

Top guest favorite
A modern blue house is nestled within lush greenery, featuring multiple large windows and a rooftop deck with an umbrella. The tranquil marshland, dotted with tall grasses, stretches into the distance under a sky filled with soft clouds.
Home in Salisbury
5 out of 5 average rating, 102 reviews

Pirates Hideaway - Sanctuary on the Marsh

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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, 292 reviews

2 Bedroom Beach Bungalow, Steps from the Beach!

Guest favorite
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, 223 reviews

Spacious waterfront free parking &Wi-fi

Guest favorite
Home in Annisquam
4.95 out of 5 average rating, 37 reviews

Private Beach!

Superhost
An aerial view captures a row of beachfront homes bordered by a sandy beach and gentle waves. The shoreline is lined with rocky formations, and the contrasting textures of the homes and surrounding landscape create a coastal atmosphere.
Home in Rockport
4.85 out of 5 average rating, 48 reviews

4BR Oceanfront Rockport Vacation on Long Beach!

Guest favorite
A serene waterfront scene captures calm waters reflecting clear blue skies. Boats are anchored in the bay, and a rocky shore is framed by lush greenery. In the distance, a quaint building with a blue roof stands on a pier, adding a touch of charm to the coastal view.
Home in Annisquam
5 out of 5 average rating, 8 reviews

Stroll to SeaView/Beach; Great Yard

Guest favorite
A spacious deck area is shown, featuring comfortable seating arrangements in various bright colors. Umbrellas provide shade over the seating. A sandy area leads up to the beach, with a white fence enclosing the yard and neighboring houses visible in the background.
Home in Salisbury
4.97 out of 5 average rating, 32 reviews

Adorable spacious renovated private home on 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, 15 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, 132 reviews

Newly remodeled home with ocean views!

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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 340 vacation rentals in Annisquam, over 260 vacation rentals in West Gloucester, and over 260 vacation rentals in Riverview.

  • 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 boutique hotel rentals in Gloucester?

    Experience the best of Gloucester with our boutique hotel rentals, starting at about $260 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

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