Gloucester holiday rentals

We found 774 holiday rentals — enter your dates for availability
Discover a selection of 170 homes, 44 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:30 Oct - 6 Nov

Image gallery for It’s All Good • Game Room • EV Charger • A/C

The closed in porch - this area is heated and cooled with it's own mini-split system. There is a pool/air hockey table, seating for 10 at the table, and another seating area with a sectional and chairs
9.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

It’s All Good • Game Room • EV Charger • A/C

Newbury

8% off
Price is AU$7,775
for 7 nights, 1 home
AU$1,111 per night
includes taxes & fees
It’s All Good • Game Room • EV Charger • A/C

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Why visit Gloucester

  • Coastal charm: Gloucester's scenic beaches and picturesque waterfront offer a tranquil seaside retreat.
  • Maritime heritage: Explore the city's rich fishing history and historic districts, echoing its storied past.
  • Historical landmarks: Discover charming historical houses and museums that celebrate the local maritime legacy.
  • Outdoor adventures: Enjoy coastal walks and the natural beauty of nearby Cape Ann's landscapes.
  • Local culture: Immerse yourself in the vibrant fishing community and experience the authentic local atmosphere.

Popular types of accommodation in Gloucester

Discover Gloucester, Massachusetts – a charming coastal city rich in maritime heritage and scenic beauty. Explore popular holiday rentals, from private holiday homes to apartments and condos. Whether you’re visiting the historic waterfront or experiencing local attractions, our Gloucester holiday rentals offer the perfect home base for your adventures. Browse our rental listings in Gloucester MA for a delightful stay in this vibrant community.

  • Private Holiday Homes: The top choice for visitors seeking a comfortable and spacious retreat, perfect for families or groups.
  • Apartments: A popular option for those wanting a central location, offering convenience and modern amenities.
  • Condos: These stylish accommodations provide a blend of comfort and luxury, ideal for a relaxing getaway.
  • Cottages: Quaint and cosy, cottages offer a charming escape, often nestled in picturesque surroundings.
  • House Boats: For a unique experience, staying on a houseboat allows you to enjoy the tranquil waters and scenic views.**

Top attractions in and around Gloucester

Gloucester, Massachusetts offers a delightful coastal retreat with its picturesque beaches, historic houses, and engaging museums. The city's rich maritime heritage and scenic coastal views make it an ideal destination for those seeking culture, outdoor adventures, and a serene seaside experience. Enjoy exploring its beaches and historical landmarks, ensuring a memorable holiday immersed in local charm and natural beauty.

  • Wingaersheek Beach: Enjoy the coastal charm of this beach, known for its relaxed seaside ambience and scenic vistas, perfect for a leisurely day by the water.
  • Hammond Castle: Experience a slice of history and romance in this unique castle, offering cultural insights and enchanting surroundings nestled within Gloucester.
  • Cape Ann: Appreciate the natural beauty and striking coastal scenery of this cape, located 6km from Gloucester, ideal for picturesque walks and seafront views.

Things to do recommended for couples

Seeking a romantic escape in Gloucester? Enjoy a sunset stroll along the picturesque Good Harbour Beach or indulge in a candlelit dinner at a charming waterfront restaurant. Don't forget to explore the historic streets and visit local art galleries for a truly memorable experience.

Things to do recommended for families

Families can explore Gloucester's scenic harbour, enjoy a boat trip to spot whales, and visit local museums to learn about maritime history. A stroll along the charming seaside promenade is sure to delight all ages.

Things to do recommended for groups

Groups visiting Gloucester can enjoy a whale-watching tour to witness majestic marine life, explore the historic Fort Defiance, and indulge in fresh seafood at local eateries. A stroll along the picturesque beaches and harbours offers a quintessential New England experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Gloucester

If you're travelling with a group, family, pets, or seeking longer stays, it's important to filter your options according to your key priorities. Here are some helpful booking tips for your Stayz experience.

  • Traveling to Gloucester with a group: Take into account the number of bedrooms you require, along with amenities like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily apply filters for these features and many others on Stayz.
  • Traveling to Gloucester with young kids: Travelling with young children can be demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is advisable.
  • Taking your pets with you to Gloucester: For many, a family holiday feels incomplete without their four-legged companions. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Gloucester: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include additional amenities in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay in and around Gloucester

Gloucester, Massachusetts, is a charming coastal city offering a perfect blend of history and natural beauty. Wander along the picturesque waterfront, explore the historic districts, and enjoy the stunning beaches that invite relaxation. The vibrant fishing community adds a unique character, while the nearby scenic areas of Cape Ann provide exceptional outdoor experiences. Whether you're seeking a tranquil escape or a glimpse into the region's maritime heritage, Gloucester promises a delightful and memorable holiday.

  • North Shore: Situated 5km from Gloucester, North Shore offers a delightful blend of outdoor pursuits, sandy beaches and family-friendly experiences. Renowned for its educational attractions, bustling shopping centres and expansive shopping mall, it provides visitors with a rich selection of activities. The local landscape is adorned with the shimmering beach, a designated family beach area and a picturesque lake, inviting travellers to enjoy a refreshing coastal retreat with a variety of leisure opportunities.
  • Annisquam: Nestled in the vicinity of Gloucester, Annisquam is celebrated for its captivating beach views, scenic surroundings and outdoor adventures. Ideal for those seeking a blend of relaxation and activity, this neighbourhood boasts access to an arts centre, thrilling amusement rides and a well-maintained golf course. Landmarks such as its sandy beach, family beach area and the dramatic cape add to the charm and allure of this coastal enclave.
  • Magnolia: Located near Gloucester, Magnolia is a neighbourhood favoured for its inviting beach atmosphere, outdoor activities and scenic vistas. It offers a range of pursuits including educational venues, recreational areas and a modern shopping mall centre. The presence of a beautiful beach, a family beach spot and a serene lake further enhances the locale, making it an appealing destination for travellers eager to immerse themselves in a vibrant, coastal setting.

Best time to go to Gloucester

If you're planning a trip to Gloucester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.1°F (-0.5°C)Light RainMostly SunnyModerately LowSlightly Low
February31.8°F (-0.1°C)Light RainMostly SunnyAverageSlightly Low
March36.7°F (2.6°C)Light RainMostly SunnyAverageSlightly Low
April45.1°F (7.3°C)Light RainMostly SunnyAverageAverage
May54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
June62.4°F (16.9°C)Light RainMostly SunnyModerately HighSlightly High
July69.6°F (20.9°C)Light RainMostly SunnyModerately HighSlightly High
August69.4°F (20.8°C)Light RainMostly SunnyModerately HighSlightly High
September64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
October55.2°F (12.9°C)Light RainMostly SunnyAverageAverage
November45.1°F (7.3°C)Light RainMostly SunnyModerately LowAverage
December37.4°F (3.0°C)Light RainMostly SunnyModerately LowAverage

Booking with Stayz is simple

Are you hoping to make your next journey more affordable? Being flexible with your travel dates can lead to better deals, as prices often fluctuate. Additionally, consider booking a longer stay, as this can result in substantial savings. To discover a Stayz property that suits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's Trip Board provides a dedicated area for you to plan new trips, manage your existing arrangements, or review your bookings in an organised manner. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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)
  • Bewitched in Salem (13.2 mi / 21.2 km)
  • The Collection (17.3 mi / 27.9 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.

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