Gloucester holiday rentals

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Discover a selection of 158 homes, 40 apartments and other holiday rentals in Gloucester that are perfect for your trip. Holiday homes provide the best amenities for you and your friends, family or even pets, such as a hot tub and a washer and dryer. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Gloucester

Showing deals for:3 Oct - 10 Oct

Exceptional

(7 reviews)

NEW 2BR Historic Marblehead Home+Minutes to Beach

Marblehead, MA

8% off

AU$1,682 per night

includes taxes & fees

Exceptional

(16 reviews)

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Rockport, MA

8% off

AU$713 per night

includes taxes & fees

Exceptional

(16 reviews)

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Gloucester, MA

8% off

AU$595 per night

includes taxes & fees

Welcome to Plum Island Cottage! A private house with a backyard and deck.

Exceptional

(69 reviews)

Former Carriage House on Plum Island Massachusetts

Newburyport, MA

8% off

AU$624 per night

includes taxes & fees

Cozy and uniquely designed living room space on the lower level

Exceptional

(8 reviews)

2 Bd/2 Bth with ·King bed ·2 floors · Private Parking · Downtown Rockport

Rockport, MA

8% off

AU$640 per night

includes taxes & fees

This bedroom features another King Size bed and convenient remote workspace

Exceptional

(20 reviews)

The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·

Rockport, MA

8% off

AU$684 per night

includes taxes & fees

Exceptional

(56 reviews)

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Marblehead, MA

8% off

AU$1,151 per night

includes taxes & fees

Exceptional

(117 reviews)

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

Gloucester, MA

8% off

AU$635 per night

includes taxes & fees

The studio is a light and bright yet colorful open space

Exceptional

(16 reviews)

NEW Rockport Studio · Walk to Bearskin Neck · Reserved Parking

Rockport, MA

8% off

AU$513 per night

includes taxes & fees

Exceptional

(6 reviews)

NEW 1BR on Salem Common l Steps to Witch Museum and Downtown l Fenced in Yard

Salem, MA

8% off

AU$1,371 per night

includes taxes & fees

Queen bed. Skylights (and their shades) are remote controlled.

Exceptional

(6 reviews)

Airy, book-lined cottage on historic seaside estate with private beaches & more

Gloucester, MA

8% off

AU$439 per night

includes taxes & fees

Exceptional

(48 reviews)

Harborfront House Directly on Rockport’s Quiet and Beautiful Old Harbor

Rockport, MA

15% off

AU$540 per night

includes taxes & fees

Welcoming Living Room: Sink into the plush sofa and enjoy your favorite shows on the Smart TV,perfect for a cozy spring retreat!

Exceptional

(13 reviews)

*Spacious 3BR Halloween|Downtown Salem+Beverly

Beverly, Massachusetts

8% off

AU$1,648 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Gloucester

Wingaersheek Beach

Find the best place to stay - Gloucester

Showing deals for: 30 Sept - 3 Oct

Coastal Comfort—Walk to Beach & Cafés

Sleeps 6 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$820 per night

includes taxes & fees

Walk to Good Harbor Beach, pet friendly, family beach home

Sleeps 8 · 3 bedrooms · 1+ bathroom

for 3 nights, 1 home

AU$773 per night

includes taxes & fees

Centrally located charmer with expansive patio, board games, & central AC

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 home

AU$448 per night

includes taxes & fees

Living/dining room with slider to deck overlooking Wonson Cove

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

Sleeps 3 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

AU$438 per night

includes taxes & fees

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Sleeps 8 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$1,102 per night

includes taxes & fees

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Our Book with Confidence Guarantee gives you 24/7 support
More quality time
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All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

The historical area of Gloucester awaits your stay

Come and experience Gloucester and its monuments, history and art galleries. This city's seaside, beaches and whale watching draw many visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Gloucester

Are you searching for things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Gloucester a fun place to get away to. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

Salem Willows Park (11.8 mi / 19 km)
Water Park of New England (15.6 mi / 25.2 km)
The Collection (17.3 mi / 27.9 km)
Sagamore Spring Golf Club (19.5 mi / 31.4 km)
Appleton Farms Grass Rides (11.1 mi / 17.9 km)
Dogs by Design & Cats Too (11.5 mi / 18.4 km)

Exploring the natural features in Gloucester

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Gloucester. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

Pavilion Beach (0.2 mi / 0.4 km)
Half Moon Beach (0.9 mi / 1.4 km)
Stage Fort Park (0.9 mi / 1.4 km)
Niles Beach (1.2 mi / 1.9 km)
Good Harbor Beach (1.7 mi / 2.8 km)
Long Beach (2.7 mi / 4.3 km)

Seasonal weather averages in Gloucester

If you're planning a holiday around the weather, July, August, September and June are the hottest months to visit, when temperatures average 19°C.

Travelling to and around Gloucester

The nearest airport is in Beverly, MA (BVY-Beverly Municipal), located 12.8 mi (20.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Lawrence, MA (LWM-Lawrence Municipal), which is 24.3 mi (39.1 km) away.

If you prefer train travel, make your way to Gloucester Station or West Gloucester Station to see more of the city.

Frequently asked questions

What is the best area to stay in Gloucester when booking a holiday home?

One of the most popular areas to get a holiday home in Gloucester is Annisquam. Discover a dream stay on Stayz and explore this area as a local.

What is the most popular type of holiday home accommodation in Gloucester?

The most popular types of holiday homes in Gloucester are houses. Searching for something different? Stayz has plenty of options to match our guests' needs, so you'll see holiday homes in lots of shapes and sizes. The ideal home away from home is waiting for you --- grab yours today.

How much does it cost to rent a holiday home in Gloucester?

Season, property type and length of stay are some things that can affect the price of a holiday home. Simply enter your travel dates to find your perfect fit. From cosy cabins to plush villas, all Stayz holiday homes offer unbeatable value.

How much does it cost to rent a beach house in Gloucester?

The average price for a holiday home close to the beach in Gloucester depends on when you're travelling and the size and style of property you want. You can quickly and easily find prices on Stayz by entering your preferred travel dates and destination. Then make use of the filter tool to select the number of bedrooms and amenities essential to you, like air conditioning, a pool and WiFi.

Are there pet-friendly holiday homes in Gloucester?

Yes. You'll have your pick of 74 holiday homes that allow pets in Gloucester. Lots of our pet-friendly holiday homes even come with an outdoor space for your furry friend to run around in, doggie beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect holiday home on Stayz.

Can I rent a house with a pool in Gloucester?

Grab your swimsuit and goggles, because there are two houses with a private pool in Gloucester. Kick back at one of these popular holiday homes and you'll enjoy pool days every day. Simply enter your travel dates into Stayz, then use the "pool" filter to find the perfect place to make a splash!

What are popular home amenities in Gloucester?

When it comes to home amenities that people search for in Gloucester, a firepit, a chef and tennis are the most popular. With Stayz holiday homes, you'll find options to suit your style and taste, whether you're travelling with family, friends or even pets.

Are there large group holiday homes in Gloucester?

Choose from 13 holiday homes in Gloucester that can accommodate 10 or more people. Whether you're organising a trip with the family or an event like a party, there's enough space to get your group together under the same roof.

Are there holiday homes in Gloucester that welcome kids?

Bring the whole group together for a fun-filled adventure in Gloucester at one of our 74 family-friendly holiday homes. Many of these stays feature amenities that are suitable for trips with children, including dining rooms, living rooms and swimming pools. Just click on the "Properties good for families" filter and select your favourite.

What are the top attractions for families in Gloucester?

Keep your kids occupied at these fun family-friendly attractions in Gloucester:

Good Harbour Beach
Hammond Castle
Wingaersheek Beach

Are there one-bedroom holiday homes in Gloucester?

You'll find 11 one-bedroom properties in Gloucester to select from. A one-bedroom holiday property is a superb choice if it's just two of you or if you're travelling on your own. Add in more space, convenience and privacy than a hotel, and you're bound to have a memorable getaway.

Can I find two-bedroom holiday homes in Gloucester?

Take off with your loved ones and enjoy a relaxing escape in one of the 18 two-bedroom holiday properties Gloucester has to offer.

Are there holiday homes with WiFi in Gloucester?

Gloucester has 22 holiday homes with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Stayz homes make it a cinch to go online.

How can I find holiday homes with air conditioning in Gloucester?

Pick from 59 Stayz holiday homes with air conditioning in Gloucester providing that gentle, cool breeze and extra level of comfort. Just enter your travel dates and then use our handy filters to look for properties with air conditioning.

How old do you have to be to rent a holiday home in Gloucester?

It's a good idea to check with the Gloucester holiday property you want on Stayz as age restrictions vary. However, it's typically 16, 18 or 21.

How long can I rent a holiday home in Gloucester for?

It all depends on the Gloucester property. To see a list of options offering extended stays, just type your travel dates and number of people into Stayz. Enjoy having the whole place to yourself, as well as amenities such as air conditioning, a kitchen and a yard where your little ones can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.