Gloucester holiday lettings

We found 706 holiday rentals — enter your dates for availability

Discover a selection of 156 homes, 39 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:10 Oct - 17 Oct

Why visit Gloucester

  • Scenic Beaches: Relax on Gloucester's stunning beaches, ideal for sunbathing, swimming, and enjoying the coastal views.
  • Rich History: Discover charming historic houses and fascinating museums that showcase the town's vibrant past.
  • Cultural Experience: Immerse yourself in the local culture, with delightful neighbourhoods offering unique shops and eateries.
  • Outdoor Adventures: Enjoy a range of outdoor activities, from hiking to ocean adventures, perfect for nature lovers.
  • Varied Accommodation: Choose from a range of holiday rentals, including spacious homes and cosy apartments to suit every need.

Popular types of accommodation in Gloucester

Explore an array of holiday rentals in Gloucester, where options such as houses, apartments, and flats cater to every traveler's needs. Whether you're seeking a spacious house rental for a family getaway or a cosy apartment rental for a romantic retreat, Gloucester has something for everyone. Let us help you find the perfect accommodation for your stay in this charming city.

  • Houses: The top choice for visitors to Gloucester, these homes offer spacious and comfortable living, perfect for families or groups.
  • Apartments: A popular option for those seeking modern amenities and convenience, ideal for couples or solo travellers.
  • Condos: Offering a blend of luxury and practicality, condos are a great choice for those looking for a stylish stay.
  • Cottages: Quaint and charming, these are perfect for a cosy getaway, often located near the coast.
  • House Boats: A unique experience, staying on a houseboat lets you enjoy the beauty of Gloucester’s waters.**

Top attractions in and around Gloucester

Gloucester is an ideal destination for those seeking a beach, outdoor, and scenic holiday. Visitors can explore a variety of attractions, including picturesque beaches, charming historic houses, and fascinating museums. This vibrant town offers a rich cultural experience, perfect for travellers looking to immerse themselves in both nature and history.

  • Wingaersheek Beach: A stunning beach with soft sands and gentle surf, perfect for sunbathing and leisurely strolls. The tranquil atmosphere invites relaxation, making it an ideal spot for families and couples alike.
  • Cape Ann: Just 2.5km from Gloucester, this picturesque cape boasts breathtaking coastal scenery and charming beaches. It's a haven for outdoor enthusiasts, offering opportunities for hiking, photography, and immersing oneself in nature.
  • Hammond Castle: Nestled in Gloucester, this enchanting castle combines medieval architecture with romantic vibes. Explore its captivating rooms and beautiful gardens, steeped in culture and history.

Things to do recommended for couples

For a romantic getaway in Gloucester, enjoy a captivating concert at Shalin Liu Performance Center, embark on an adventurous whale watch with Capt Bill & Sons, or savour delightful wines at Mill River Winery. Each experience offers a unique ambiance perfect for couples.

Things to do recommended for families

Families can explore the serene Halibut Point Reservation, just 2.5km from Gloucester, or enjoy thrilling rides at the Water Park of New England, 9.9km away. For a fun-filled day, visit the arcade at Salem Willows Park, located 7.5km from Gloucester.

Things to do recommended for groups

Groups visiting Gloucester can hike the scenic trails of Dogtown for a taste of adventure, enjoy a captivating performance at the Gorton Theatre for a blend of culture and family fun, and unwind with drinks at Ipswich Bar, perfect for a romantic evening out.

Booking with Vrbo is simple

Are you hoping to cut costs on your next holiday? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay in and around Gloucester

Gloucester, Massachusetts, offers an enchanting blend of history and scenic beauty, perfect for a memorable beach getaway. Families will adore the friendly atmosphere and stunning coastal views, while those seeking an elegant retreat can indulge in the charming local culture. Whether exploring the vibrant neighbourhoods or basking on the picturesque beaches, Gloucester promises a delightful experience for every traveller. Don’t miss the chance to revel in its captivating charm and upcoming ocean adventures!

  • Rockport: Located a mere 2.5km from Gloucester, Rockport is a charming seaside town known for its stunning beaches and picturesque outdoor scenery. Visitors can enjoy a variety of outdoor activities, from relaxing on the family-friendly beaches to exploring the scenic coastal paths. The vibrant local arts scene comes alive with frequent music concerts and cultural events, making it an ideal spot for families and art enthusiasts alike. Don't miss the chance to visit local landmarks such as the iconic Cape Ann and its scenic beaches, where you can soak up the sun or enjoy a leisurely stroll along the shore.
  • North Shore: Just 1.9km from Gloucester, the North Shore is a delightful destination perfect for families and couples seeking outdoor adventures and romantic getaways. This coastal region offers a plethora of shopping options, from quaint boutiques to larger shopping centres, ensuring there’s something for everyone. The area is also home to beautiful beaches and serene lakes, ideal for a relaxing day by the water. Take in a performance at one of the local theatres, or enjoy a lovely meal at a waterfront restaurant while soaking in the stunning views.
  • Annisquam: Nestled around Gloucester, Annisquam is a quaint neighbourhood that attracts visitors with its tranquil outdoor spaces and family-friendly beaches. This charming area offers various recreational activities such as golfing and visiting local arts centres. The scenic beauty of Annisquam is complemented by its proximity to serene lakes and beautiful beaches, making it an excellent choice for families looking to spend quality time together. Enjoy a leisurely afternoon exploring the picturesque surroundings or catch a performance at the local theatre for a taste of the vibrant arts scene.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

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

If you're travelling with a group, family, or pets, or if you're considering an extended stay, it's essential to filter your options based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Gloucester with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Gloucester with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, along with suitable facilities 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 truly finished without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Gloucester: If you're in search of holiday rentals offering great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a helpful platform for planning your journeys, allowing you to start new trips, continue from where you last stopped, or manage and view your itineraries. You can easily find the properties you've saved or booked, organised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/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)
  • 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 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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