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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

Guest favorite
A cozy bedroom features a spacious bed adorned with a colorful quilt and is positioned near a large window. Sheer curtains frame the window, providing a view of the harbor and boats outside. A softly illuminated bedside lamp adds a warm touch to the room.
Apartment in Rockport
4.95 out of 5 average rating, 154 reviews

Spectacular Views of Rockport Harbor.

Guest favorite
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, 107 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, 287 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, 262 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
4.98 out of 5 average rating, 122 reviews

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

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
4.89 out of 5 average rating, 196 reviews

The Waterline – A Private Harborfront Retreat

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, 203 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, 261 reviews

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

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, 116 reviews

Hillside

Top guest favorite
A traditional farmhouse is visible alongside a red barn, set against a backdrop of autumn foliage. The well-maintained lawn features neatly trimmed shrubs and trees, with the clear sky overhead highlighting the peaceful rural setting.
Home in Newton
4.98 out of 5 average rating, 104 reviews

Winnie's Place - Freshly Renovated 1800s Farmhouse

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 Plum Island
4.99 out of 5 average rating, 165 reviews

“Salty Girl” Plum Island, MA

Top guest favorite
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.
Home in Salem
4.94 out of 5 average rating, 173 reviews

Quaint Little New Hampshire Lake House Getaway!

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, 109 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, 209 reviews

Stagehill Beach House

Top guest favorite
A waterfront home is shown with expansive windows, situated directly by the water. A private dock extends toward the water, accompanied by a set of stairs leading down from the deck. Nearby, a separate guest house is visible, framed by greenery.
Home in Gloucester
5 out of 5 average rating, 15 reviews

Stay at Rocky Neck

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, 206 reviews

Gloucester Private Contemporary 4 bedrooms

Beach house rentals in Gloucester

Top 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, 231 reviews

Spacious waterfront free parking &Wi-fi

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, 302 reviews

2 Bedroom Beach Bungalow, Steps from the Beach!

Guest favorite
A sandy beach area is equipped with a gas grill, dining table, and lounge chairs under a large umbrella. Kayaks are neatly arranged along the shoreline, while a view of the calm water and distant boats is visible beneath the clear blue sky.
Home in Annisquam
4.95 out of 5 average rating, 42 reviews

Private Beach!

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, 36 reviews

Adorable spacious renovated private home on beach

Top guest favorite
The great room is highlighted by 25-foot ceilings and panoramic windows offering views of the ocean. A large sectional sofa surrounds a coffee table, while a flat-screen TV is mounted above the fireplace. Sliding glass doors lead to an outdoor space, enhancing the airy feel.
Home in Swampscott
4.92 out of 5 average rating, 106 reviews

Ocean Views at Casa de Mar near Salem & Boston

Top guest favorite
A private dock extends over gentle waters, complemented by two kayaks in a vibrant blue hue. The sun sets in the background, casting warm light across the scene, while a floating raft drifts nearby amidst lush greenery lining the shore.
Home in Gloucester
5 out of 5 average rating, 20 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 North Weymouth
4.94 out of 5 average rating, 134 reviews

Newly remodeled home with ocean views!

Guest favorite
A cozy living room features a mix of furnishings, including a blue sofa, a white slipcovered couch, and a plush armchair. A rustic coffee table is centered, with a gas fireplace and a television on a stand nearby. Large windows provide natural light and offer ocean views.
Home in Rockport
4.95 out of 5 average rating, 21 reviews

Cozy Beach Home with Ocean Views

Quick stats about vacation rentals in Gloucester

  • Total rentals

    590 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    28K reviews

  • Family-friendly rentals

    390 properties are a good fit for families

  • Pet-friendly rentals

    160 properties allow pets

  • Rentals with a pool

    10 properties have a pool

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 West Gloucester, and over 330 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 condo rentals in Gloucester?

    Experience the best of Gloucester with our condo rentals, starting at about $100 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 100 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 100 homes with a bbq area, over 10 homes with a gym, over 90 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

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