Gloucester holiday homes

We found 770 holiday rentals — enter your dates for availability

Discover a selection of 167 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:2 Oct - 9 Oct

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Why visit Gloucester

  • Scenic beaches: Gloucester boasts beautiful sandy beaches perfect for relaxation and coastal walks.
  • Rich maritime history: Discover the city’s fascinating heritage through its historic houses and museums.
  • Outdoor adventures: Engage in various activities like kayaking, fishing, and hiking along the picturesque coastline.
  • Charming town atmosphere: Experience the inviting local culture and community vibe in this family-friendly seaside town.
  • Stunning fall colours: Enjoy breathtaking autumn foliage that enhances the beauty of Gloucester's landscapes.

Top attractions in and around Gloucester

Gloucester, Massachusetts offers a delightful blend of scenic beaches, historic houses, and intriguing museums. Visitors can immerse themselves in local culture while enjoying outdoor adventures along its picturesque coastline. Whether you're keen on exploring beachside walks or delving into the city's rich heritage, Gloucester provides a charming retreat for those seeking a mix of relaxation and cultural discovery.

  • Cape Ann: Experience dramatic coastal scenery and beaches just 6km away from Gloucester, offering a picturesque seaside retreat.
  • Plum Cove Beach: Enjoy the local beach vibes at this Gloucester gem, perfect for a relaxing day by the sea.
  • Salem Common: Discover a vibrant urban park 21km from Gloucester, providing family-friendly outdoor spaces with a city feel.

Things to do recommended for couples

Enjoy a romantic getaway in Gloucester, Massachusetts, where you can wander hand in hand along charming coastal paths and savour local seafood cuisine. Explore unique art galleries, and capture memories in quaint harbour settings with your loved one.

Things to do recommended for families

Families can explore the maritime history at the Cape Ann Maritime Museum, enjoy a scenic walk along the harbor, and savour local seafood at family-friendly eateries in Gloucester.

Things to do recommended for groups

Groups visiting Gloucester can enjoy whale watching tours and explore the local art scene, experiencing the coastal charm with scenic harbour views and lively local markets.

*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

Whether you're journeying with a group, with your whānau, bringing your pets along, or planning an extended stay, be sure to set the appropriate filters. Here are some Vrbo booking tips tailored for you.

  • Traveling to Gloucester with a group: Consider how many bedrooms you'll require, along with features like a fully equipped kitchen or an outdoor area suitable for group gatherings. Fortunately, you can easily filter for all of these options—and more—on Vrbo.
  • Traveling to Gloucester with young kids: Journeying with young ones can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Gloucester: For many, a family holiday isn’t whole without their four-legged companion. If that resonates with you, explore Vrbo properties that welcome pets. Many pet-friendly homes come equipped with feeding bowls and beds, ensuring everyone feels comfortable and at home.
  • Planning for a long term stay visiting Gloucester: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Gloucester

Gloucester offers a perfect coastal escape with its sandy beaches, rich maritime history, and picturesque town green. Enjoy a relaxing stay, explore the local history, and take in the fall colours in this charming, family-friendly seaside town. It’s an ideal destination for those seeking a mix of outdoor adventure and historical vibes, right in the heart of Gloucester, Massachusetts.

  • North Shore: Located 5km from Gloucester, North Shore is a delightful destination for families and outdoor enthusiasts alike. With its beautiful beaches and scenic lakes, visitors can enjoy a variety of activities including swimming, picnicking, and hiking. The area is also home to a vibrant shopping mall and centre, making it convenient for those looking to combine leisure with a bit of retail therapy. Whether you're exploring the picturesque coastline or engaging in family-friendly activities, North Shore offers a welcoming atmosphere for all.
  • Rockport: Just 6km from Gloucester, Rockport is a charming coastal city known for its breathtaking scenery and inviting beaches. This picturesque locale is perfect for those seeking outdoor adventures, from leisurely walks along the shore to exploring its beautiful recreational areas. Rockport is also a hub for arts and culture, with music concerts and educational events that reflect the local community's vibrant spirit. The iconic cape and family-friendly beaches add to its allure, making it an ideal spot for relaxation and exploration.
  • Manchester-by-the-Sea: Situated 10km from Gloucester, Manchester-by-the-Sea is a quaint city that embodies the quintessential New England charm. Visitors flock here for its stunning beaches and outdoor experiences, including scenic walks and golfing at local courses. The area is rich in natural beauty, with captivating coastal views and peaceful parks perfect for a day out. With its combination of recreation, education opportunities, and picturesque landscapes, Manchester-by-the-Sea offers a serene escape for those looking to unwind and connect with nature.

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.

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

Booking with Vrbo is a breeze

Are you keen to save on your next adventure? Think about being flexible with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of holiday rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is a handy tool that allows you to plan new adventures, keep track of your existing arrangements, and manage your bookings with ease. Your saved or reserved properties are conveniently categorised into Potential, Upcoming, or Current Trips. To check out the Trip Boards, head over to: https://www.bookabach.co.nz/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:

  • Mill River Winery (14.5 mi / 23.4 km)
  • Water Park of New England (15.6 mi / 25.2 km)
  • Appleton Farms Grass Rides (11.1 mi / 17.9 km)
  • Salem Willows Park (11.8 mi / 19 km)
  • Mud Puddle Toys (12 mi / 19.4 km)
  • Stowaway Sweets (13 mi / 21 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 Bookabach 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? Bookabach 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 Bookabach 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 Bookabach 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 Bookabach.
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 Bookabach, 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 Bookabach 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 Bookabach homes make it a cinch to go online.
How can I find holiday homes with air conditioning in Gloucester?
Pick from 59 Bookabach 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 Bookabach 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 Bookabach. 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.