Gloucester holiday lettings

We found 692 holiday rentals — enter your dates for availability

Discover a selection of 163 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:15 May - 22 May

Image gallery for ❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

Essex River is one of the main waterways in what is called The Great Marsh
9.6 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)

❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

Essex

20% off
Price is £2,336
for 7 nights, 1 home
£334 per night
includes taxes & fees
❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • 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)
  • Witch Mansion (13.3 mi / 21.4 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:

  • 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?
When considering a holiday rental in Gloucester, Massachusetts, you might find the charming neighbourhood of East Gloucester particularly appealing. This area is known for its stunning coastal views and picturesque beaches, making it great for those who appreciate nature and the seaside. Nearby, you can explore the famous Good Harbour Beach, ideal for sunbathing and swimming, or take a leisurely stroll along the scenic Cape Ann Path.

Another excellent option is the Historic Downtown area, where the rich maritime history of Gloucester comes to life. Here, you can visit the Cape Ann Museum, which showcases the region's art and heritage, and enjoy the vibrant setting filled with shops and delightful eateries. The downtown area offers a variety of rental properties, suiting different tastes and budgets, making it a convenient choice for visitors looking for convenience and local culture.
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, consider the scenic area around Good Harbor Beach, which is known for its beautiful sandy shores and family-friendly atmosphere. This beach offers a range of holiday rentals, from charming cottages to spacious homes, many of which come with amenities such as outdoor decks, barbecue grills, and fully equipped kitchens. These features are ideal for families and groups looking to enjoy the coastal setting while having the convenience of cooking their own meals.

Another popular area is Long Beach, which provides a more tranquil atmosphere with stunning ocean views. Here, you'll find properties that often include private beach access, outdoor showers, and ample living space for relaxation. The proximity to local seafood restaurants and shops adds to the appeal, making it easy for visitors to enjoy fresh catches and local cuisine.

Additionally, the historic district around Cape Ann offers unique options, including renovated fishermen's houses and waterfront properties that highlight the region's maritime heritage. Many of these rentals feature cozy interiors, charming decor, and amenities such as fireplaces or patios, superb for enjoying the seaside ambiance.
What is the most popular type of holiday rental accomodation in Gloucester?
In Gloucester, holiday houses are the most popular type of holiday rental, with about 560 available throughout the area. These properties are often situated in scenic locations near the waterfront, providing easy access to local beaches and attractions such as the Cape Ann Museum and the historic Gloucester Harbour. Most holiday houses come equipped with amenities like fully stocked kitchens, spacious living areas, and outdoor decks or patios for enjoying the coastal views.

Additionally, there are around 132 apartments available, typically found in vibrant neighbourhoods close to shops and restaurants. These apartments offer conveniences such as modern kitchens and comfortable living spaces. For those seeking a quaint experience, approximately 60 cottages are also on offer, often located in peaceful settings, superb for a romantic getaway or a family retreat.
Are there any family house rentals in Gloucester?
In Gloucester, Massachusetts, there are numerous family-friendly house rentals available—approximately 130 options throughout the area. Visitors can explore charming neighbourhoods such as East Gloucester, which offers easy access to the picturesque beaches and scenic views along the coast. Many of these homes feature spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces superb for barbecues and relaxation.

Amenities like Wi-Fi and laundry facilities are commonly included, ensuring a comfortable stay for families. The nearby Good Harbor Beach and Wingaersheek Beach are ideal for a day of sun and sand, while the town's rich maritime history can be discovered at local attractions like the Cape Ann Museum.
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 feature pools and hot tubs. This charming coastal city offers a variety of neighbourhoods where these properties can be found, including the picturesque waterfront areas and the serene settings of nearby Annisquam.

Travellers can expect many amenities in these rentals, such as private swimming pools, relaxing hot tubs, outdoor patios for al fresco dining, and fully equipped kitchens, great for family gatherings or entertaining friends. Some properties may also include additional features like barbecue grills and spacious gardens, allowing guests to fully enjoy the coastal lifestyle while providing a comfortable retreat after a day of exploring the beautiful surroundings.
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 about 57 options to choose from. Many of these properties are situated near the picturesque coastline, offering stunning views and easy access to the beach. Travellers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.

The city's vibrant neighbourhoods like East Gloucester and Lanesville provide a charming atmosphere, with local shops and dining options just a stone's throw away. Additionally, nearby parks and nature reserves offer wonderful opportunities for outdoor activities with pets, including scenic walks along the coast or through wooded trails.
Are there any remote work holiday rentals in Gloucester?
In Gloucester, Massachusetts, there are plenty of remote work holiday rentals available, with around 668 options to choose from. This coastal city not only offers a picturesque setting but also a variety of amenities that cater to those working remotely. Many properties include features such as dedicated workspaces, high-speed internet, and Wi-Fi, ensuring a productive environment.

Travellers can expect accommodations ranging from charming cottages to modern apartments, often equipped with comfortable furnishings and well-equipped kitchens for self-catering. The scenic waterfront and nearby attractions like the historic downtown area and beautiful beaches provide excellent opportunities for relaxation after a day of work. Additionally, the local culture, with its art galleries and seafood restaurants, adds to the appeal of staying in Gloucester while managing remote work commitments. 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 rental amenities often include fully-equipped kitchens, allowing guests to prepare their own meals and enjoy family dining experiences. Many properties also feature outdoor spaces such as decks or patios, great for relaxing in the fresh sea air while taking in views of the surrounding area. Onsite parking is frequently available, making it convenient for those travelling by car. Additionally, rentals commonly provide coffee and tea makers for a comforting start to the day.
When is the best time to visit Gloucester for a holiday rental?
The most popular time to visit Gloucester for a holiday rental is during the peak season from June to August. This vibrant period draws visitors who are eager to enjoy the coastal charm, fresh seafood, and a variety of outdoor activities. With warm temperatures averaging between 20 to 30 degrees Celsius, it's a great backdrop for beachgoers, those seeking boat trips, and families looking to explore the scenic beauty of Cape Ann.

July, in particular, stands out as the busiest month, bustling with tourists who flock to the area for its lively option and numerous summer events. You can look forward to enjoying arts festivals, local markets, and the picturesque beaches that make Gloucester such a beloved destination.

If you're considering a more budget-friendly visit, December offers a delightful alternative. While temperatures may dip to around 0 to 5 degrees Celsius, winter in Gloucester reveals a quieter charm. This time is ideal for those who appreciate the peaceful coastal scenery, holiday festivities, and fewer crowds, making it a unique time to explore the area's rich maritime history.

Ultimately, whether you prefer the energetic vibes of summer or the serene beauty of winter, Gloucester has something to offer every traveller.
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, visitors can explore a range of attractions that highlight the town's rich maritime history and natural beauty. The picturesque Old Gloucester area features charming historic architecture and is close to the iconic Cape Ann Museum, which showcases local art and history. Visitors can also stroll along the scenic waterfront at Stage Fort Park, where they can enjoy stunning views of the harbour and access beautiful beaches such as Cressey's Beach.

The historic Fishermen's Memorial is a poignant tribute to the town's fishing heritage, situated near the bustling harbour where you can see the local fishing fleet at work. For outdoor enthusiasts, the nearby Halibut Point State Park offers hiking trails with breathtaking coastal views and unique granite formations.
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.

More holiday ideas