Gloucester holiday lettings

We found 723 holiday rentals — enter your dates for availability

Discover a selection of 158 homes, 41 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:13 Mar - 20 Mar

Image gallery for C by the Sea - Ocean View Penthouse

Living area
10 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

C by the Sea - Ocean View Penthouse

Gloucester, MA

8% off
Price is £2,802
for 7 nights, 1 apartment
£400 per night
includes taxes & fees
C by the Sea - Ocean View Penthouse

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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.

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.

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

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.

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:

  • Dogs by Design & Cats Too (11.5 mi / 18.4 km)
  • 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)
  • Mill River Winery (14.5 mi / 23.4 km)
  • The Collection (17.3 mi / 27.9 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:

  • 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)
  • Wingaersheek Beach (2.9 mi / 4.7 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?
When considering a holiday rental in Gloucester, Massachusetts, the picturesque neighbourhood of Cape Ann is an excellent choice. This area is renowned for its stunning coastal views and vibrant arts scene, making it a delightful spot for visitors. Cape Ann is home to attractions such as the iconic Cape Ann Museum, which showcases the region's rich maritime history and artistic heritage, and the beautiful Good Harbor Beach, great for sunbathing or a peaceful stroll along the shore.

Another appealing neighbourhood is the Historic District, where you can immerse yourself in the charm of Gloucester's past. Here, you'll find beautifully preserved 18th and 19th-century architecture and easy access to the famous Fishermen's Memorial, a poignant tribute to the city's fishing heritage. The Historic District offers a range of rental properties, giving you ample options to choose from.
How much does it cost to rent a holiday home in Gloucester?
Prices for holiday rentals in Gloucester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Gloucester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Gloucester holiday house rentals?
You can find great discounts on house rentals in Gloucester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Gloucester?
For renting a beach house in Gloucester, Massachusetts, travellers should focus on the areas around Good Harbour Beach and Wingaersheek Beach. Good Harbour Beach is known for its beautiful sandy stretches and family-friendly atmosphere, making it an ideal spot for beach house rentals. Properties in this area often come with amenities such as ocean views, outdoor decks, and fully equipped kitchens, superb for enjoying meals while taking in the coastal scenery.

Wingaersheek Beach, located a bit further down the coast, offers a more serene environment with its tidal flats and calm waters. Rentals here frequently include features like private patios, outdoor showers, and access to beach gear, allowing families to make the most of their seaside experience. Visitors can also enjoy the nearby Annisquam Lighthouse, which adds a touch of historical charm to the area.
What is the most popular type of holiday rental accomodation in Gloucester?
In Gloucester, holiday houses are the most popular type of rental accommodation, with approximately 139 available throughout the area. These properties are often situated in charming neighbourhoods, close to the waterfront and local attractions like the Cape Ann Museum and the historic St. Ann's Church. Most holiday houses come equipped with fully furnished kitchens, spacious living areas, and outdoor spaces such as decks or gardens, superb for enjoying the coastal climate.
Are there any family house rentals in Gloucester?
In Gloucester, Massachusetts, there are approximately 140 family-friendly house rentals available, making it an excellent choice for those travelling with children. The neighbourhoods around the picturesque Cape Ann area offer a variety of spacious homes, many of which feature amenities such as fully equipped kitchens, large living areas, and outdoor spaces ideal for family gatherings.

Visitors will appreciate the proximity to local attractions, including the beautiful beaches of Good Harbor and Wingaersheek, where children can enjoy sandcastle building and swimming. Additionally, the nearby Gloucester Maritime Heritage Centre provides an engaging look into the region's fishing history, great for educational outings.
Can I rent a holiday home with a pool or hot tub in Gloucester?
In Gloucester, Massachusetts, there are several holiday homes available for rent that come equipped with pools and hot tubs. This picturesque coastal city offers a charming blend of maritime history and stunning ocean views, making it an ideal location for a relaxing getaway. Many of the rentals feature private pools, outdoor hot tubs, and spacious patios, superb for enjoying the scenic surroundings and warm summer evenings.
Can I find long-stay holiday rentals in Gloucester?
A long-stay holiday rental in Gloucester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Gloucester?
In Gloucester, there are numerous pet-friendly house rentals available, with around 56 options to choose from. Many of these properties are situated near the beautiful coastline and offer a variety of amenities to ensure a comfortable stay. Travellers can expect features such as fully equipped kitchens, spacious living areas, and outdoor spaces that might include decks or gardens, ideal for enjoying the fresh sea air.
Are there any remote work holiday rentals in Gloucester?
In Gloucester, Massachusetts, there are plenty of remote work holiday rentals available, with around 175 options to choose from. The area is well-known for its picturesque coastal scenery and vibrant arts scene, making it an appealing destination for those looking to combine work and leisure. Many of the properties come equipped with dedicated workspaces, including desks and ergonomic chairs, as well as reliable Wi-Fi to ensure productivity while away from home. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Gloucester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Gloucester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Gloucester?
In Gloucester, popular holiday rental amenities include fully equipped kitchens, which typically feature essential appliances such as refrigerators, microwaves, toasters, and cookware, dishware, and utensils. These amenities allow guests to prepare their own meals and enjoy the convenience of home while exploring the beautiful coastal area.
When is the best time to visit Gloucester for a holiday rental?
July is the most popular month to visit Gloucester, Massachusetts, attracting tourists keen to enjoy the vibrant summer atmosphere. During the peak season from June to August, visitors can indulge in various outdoor activities, including beach outings, whale watching, and exploring the charming waterfront. The warm summer temperatures, typically ranging from the mid-teens to low 20s Celsius, create an ideal setting for sightseeing and leisurely walks along the scenic coast.

For those who prefer a quieter experience, the shoulder months of late spring and early autumn can be quite appealing. Specifically, visiting in September allows for pleasant weather without the bustling crowds of the peak season. You can still enjoy mild temperatures, great for outdoor adventures and exploring local attractions at a more leisurely pace.

If you're looking for budget-friendly options, December is typically the low season in Gloucester. It's cooler, with temperatures often dropping to around 0°C, this month offers a unique charm, including holiday festivities and a chance to experience the town's winter beauty.
How early should I book a Gloucester holiday rental?
Book your Gloucester holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Gloucester?
In Gloucester, Massachusetts, visitors can experience firsthand a rich maritime history and natural beauty. The historic downtown area, with its charming shops and seafood restaurants, is a great starting point. Here, you can visit the Cape Ann Museum, which showcases the region's art and history, and stroll along the picturesque harbor.

The iconic Cape Ann Lighthouse, located on Rocky Neck, offers stunning views and a glimpse into the area's nautical past. For those interested in outdoor activities, Good Harbor Beach provides a beautiful sandy stretch, ideal for sunbathing and swimming.
Can I change or cancel my Gloucester home rental booking on Vrbo?
To find Gloucester holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Gloucester holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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