Gloucester holiday rentals

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.

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.

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.

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.

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.

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.

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 Stayz.

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.

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.

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.

Stayz 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.

Stayz offers a wide selection of holiday homes 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 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.

You can find great discounts on holiday homes in Gloucester on Stayz, 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.

To find Gloucester holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.

A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Stayz'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 favourites, and build the perfect itinerary together.

Book your Gloucester holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.

Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Gloucester to more spacious homes.

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.

Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.

Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.