Gloucester holiday rentals

We found 726 holiday rentals — enter your dates for availability

Discover a selection of 159 homes, 43 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:1 May - 8 May

Image gallery for Charming downtown home in the center of Historic Marblehead: 5min walk to harbor

Exterior
9.8 out of 10, Exceptional, (112 reviews)
Exceptional
(112 reviews)

Charming downtown home in the center of Historic Marblehead: 5min walk to harbor

Marblehead

7% off
Price is S$2,823
for 7 nights, 1 home
S$403 per night
includes taxes & fees
Charming downtown home in the center of Historic Marblehead: 5min walk to harbor

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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:

  • Water Park of New England (15.6 mi / 25.2 km)
  • Appleton Farms Grass Rides (11.1 mi / 17.9 km)
  • Dogs by Design & Cats Too (11.5 mi / 18.4 km)
  • Salem Willows Park (11.8 mi / 19 km)
  • Mill River Winery (14.5 mi / 23.4 km)
  • Sagamore Spring Golf Club (19.5 mi / 31.4 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 rental?
One of the most popular areas to get a holiday home in Gloucester is Annisquam. Discover a dream stay on Vrbo and explore this area as a local.
What is the most popular type of holiday rental accommodation in Gloucester?
The most popular types of holiday rentals in Gloucester are houses. Searching for something different? Vrbo 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 rental 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 Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Gloucester?
The average price for a holiday rental 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 Vrbo 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 rentals in Gloucester?
Yes. You'll have your pick of 74 holiday rentals that allow pets in Gloucester. Lots of our pet-friendly holiday rentals 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 Vrbo.
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 rentals and you'll enjoy pool days every day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Gloucester?
When it comes to rental amenities that people search for in Gloucester, a firepit, a chef and tennis are the most popular. With Vrbo 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 rentals in Gloucester?
Choose from 13 holiday rentals 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 rentals 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 rentals 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 rentals 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 rentals with WiFi in Gloucester?
Gloucester has 22 holiday rentals 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 Vrbo homes make it a cinch to go online.
How can I find holiday rentals with air conditioning in Gloucester?
Pick from 59 Vrbo holiday rentals 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 rental in Gloucester?
It's a good idea to check with the Gloucester holiday property you want on Vrbo as age restrictions vary. However, it's typically 16, 18 or 21.
How long can I rent a holiday rental 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 Vrbo. 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.

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