Gloucester vacation rentals

We found 725 vacation rentals — enter your dates for availability

Discover a selection of 162 homes, 40 apartments, and other vacation rentals in Gloucester that are perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, such as WiFi and a pool. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Gloucester

Showing deals for:May 22 - May 29

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

22% off
Price is $422
$2,954 for 7 nights
All fees included
❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

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Find out more about Gloucester

Why visit Gloucester

  • Beautiful Beaches: Gloucester boasts stunning beaches perfect for sunbathing, swimming, and beachcombing.
  • Rich History: Explore historic houses and captivating museums that showcase the area's maritime heritage.
  • Outdoor Activities: Enjoy various outdoor adventures, including hiking, kayaking, and whale watching.
  • Family-Friendly Atmosphere: The charming neighborhoods are ideal for families seeking affordable and cozy vacation rentals.
  • Local Culture: Experience the welcoming vibe and picturesque scenery, creating unforgettable memories in this coastal gem.

Popular types of accommodation in Gloucester

Discover the charm of Gloucester with a variety of vacation rentals to suit your needs. Whether you prefer a cozy private home, a modern apartment, or a spacious condo, there’s something for everyone. Our listings feature essential amenities, including laundry facilities, ensuring a comfortable stay. Explore the best house rentals and homes for rent in Gloucester, MA, and enjoy a seamless getaway with the reassurance of transparency and savings.

  • Houses: The top choice for travelers in Gloucester, these homes offer spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Apartments: A popular option for those wanting the convenience of a fully-equipped living space, ideal for couples or solo travelers.
  • Condos: These provide a blend of home-like amenities with resort-style features, making them a favored pick for visitors.
  • Cottages: Charming and quaint, cottages offer a cozy retreat for a peaceful getaway by the sea.
  • House Boats: For a unique experience, house boats provide a fun and adventurous stay on the water.**

Top attractions in and around Gloucester

Gloucester, Massachusetts, is perfect for those seeking beach, outdoor, and scenic vacations. Visitors can explore a variety of attractions such as beautiful beaches, historic houses, and engaging museums. This charming coastal town offers a rich cultural experience along with numerous outdoor activities, making it an ideal destination for travelers looking to enjoy both nature and history.

  • Wingaersheek Beach: A stunning beach with soft sand and gentle waves, perfect for sunbathing and swimming. The scenic views of the ocean create a relaxing atmosphere, making it an ideal spot for families and beachgoers.
  • Cape Ann: Located 4 miles from Gloucester, this picturesque cape offers breathtaking coastal scenery and charming beaches, perfect for outdoor activities like hiking and exploring tidal pools.
  • Hammond Castle: A romantic castle nestled in Gloucester, featuring beautiful architecture and rich history. Visitors can explore its intriguing rooms and enjoy scenic views of the ocean.

Things to do recommended for couples

For a romantic getaway in Gloucester, enjoy a captivating show at the Shalin Liu Performance Center, embark on an adventurous whale watch with Capt Bill & Sons, or savor exquisite wines at Mill River Winery. Each experience offers a perfect blend of romance and excitement.

Things to do recommended for families

Families vacationing in Gloucester can explore the serene Halibut Point Reservation for relaxation, have a splashing good time at the Water Park of New England for adventure, and enjoy arcade fun at Salem Willows Park, perfect for creating lasting memories together.

Things to do recommended for groups

Group travelers in Gloucester can hike the scenic trails of Dogtown for an outdoor adventure, enjoy a captivating show at the Gorton Theatre for a touch of culture, and browse unique finds at the Todd Farm Flea Market, just 13 miles away, for a lively local experience.

*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

When planning your trip, whether you're traveling with friends, family, or pets, or seeking extended stays, be sure to prioritize your preferences in the search filters. 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 any additional amenities like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Gloucester with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private 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 families, a vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Gloucester: If you’re searching for vacation rentals that offer special rates 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 features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Gloucester

Gloucester, Massachusetts, is a charming coastal city perfect for a summer getaway. Explore its stunning beaches and outdoor activities while soaking in the rich history of the area. Nearby neighborhoods offer a family-friendly atmosphere, making it ideal for travelers seeking affordable vacation rentals and cozy vacation homes. Enjoy friendly locals and picturesque scenery as you create unforgettable memories in this beautiful seaside destination.

  • Rockport: Rockport is a charming coastal city located 4 miles from Gloucester, known for its stunning beaches and picturesque scenery. This delightful destination offers visitors a variety of outdoor activities, from sunbathing on family-friendly beaches to exploring scenic walking trails. Rockport is also a hub for arts and culture, featuring music concerts and local art galleries. Don't miss the opportunity to visit iconic landmarks such as the Cape Ann's beaches, where you can enjoy breathtaking ocean views and a tranquil atmosphere, making it a perfect getaway for relaxation and recreation.
  • North Shore: Just 3 miles away from Gloucester, the North Shore region is a vibrant area perfect for families and couples alike. With a focus on outdoor adventures and romantic settings, North Shore boasts beautiful beaches and serene lakes ideal for picnics and leisurely strolls. The area features a variety of shopping options, including quaint boutiques and shopping malls, as well as cultural attractions like theaters showcasing local productions. Enjoy a day filled with family fun at the beach, followed by an evening of entertainment, making North Shore a well-rounded destination for all visitors.
  • Annisquam: Annisquam is a picturesque neighborhood situated around the Gloucester area, offering a peaceful coastal experience. Known for its family-friendly atmosphere and outdoor pursuits, Annisquam invites visitors to explore its charming beaches and scenic lakes. The community features local arts centers and theaters, providing enriching cultural experiences for all ages. Whether you're enjoying a day on the water or playing a round of golf, Annisquam is an ideal spot for families looking to create lasting memories in a beautiful setting.

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

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the total booking amount. Being the organizer certainly has its perks. Enroll in our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on eligible stays. Sign up today and begin earning rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or review and organize your travel arrangements. You can easily find the properties you've saved or booked in the categories of Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The historic 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 vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Gloucester

Are you searching for things to do in the city? Venture out of your cozy vacation rental and experience everything that Gloucester has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 an adventurous traveler or just want to spend some time taking in the scenery, Gloucester is a great spot to appreciate mother nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • 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 vacation around the weather, July, August, September and June are the hottest months to visit, when temperatures average 66°F.

Traveling to and around Gloucester

The nearest airport is in Beverly, MA (BVY-Beverly Municipal), located 12.8 mi (20.6 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying 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, Massachusetts, United States of America when booking a vacation rental?
When considering the best area to stay in Gloucester, Massachusetts, a fantastic option is the historic downtown area. This vibrant neighborhood offers a charming blend of coastal beauty and rich maritime history. Visitors will find themselves just a short stroll away from the picturesque harbor, where they can enjoy fresh seafood at local eateries or take a scenic boat tour. The downtown area is also home to the Cape Ann Museum, which showcases the art and culture of the region, making it a great spot for those interested in local history and art.

Another great choice is the area around Good Harbor Beach, known for its stunning sandy shores and breathtaking ocean views. This neighborhood is ideal for beach lovers and families looking to relax and soak up the sun. The beach is not only great for sunbathing but also offers opportunities for swimming and kayaking. Nearby, you can explore the scenic trails at the nearby salt marshes, providing a lovely backdrop for outdoor activities.

In both areas, you'll find a variety of vacation rentals ranging from cozy cottages to charming beach houses, ensuring that visitors have plenty of options to choose from for their stay.
How much does it cost to rent a vacation home in Gloucester?
Prices for vacation 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 vacation 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, the area around Good Harbor Beach is a top choice, offering stunning views and easy access to one of the most popular beaches in the region. Many properties here feature amenities such as outdoor decks great for enjoying the ocean breeze, large windows to take in the scenic views, and fully equipped kitchens for convenient meal preparation. This neighborhood is also close to local restaurants and shops, enhancing the overall experience for travelers.

Another excellent option is the waterfront along Cape Ann, particularly near the picturesque Annisquam River. Vacation rentals in this area often include private docks, making it ideal for boating enthusiasts. Properties can range from quaint cottages to spacious homes, many of which come with outdoor grills, fire pits, and family-friendly amenities like game rooms. This location offers a peaceful retreat while still being a short drive from Gloucester's bustling downtown, where visitors can explore galleries, seafood markets, and charming boutiques.

For those interested in a more tranquil setting, consider the Rocky Neck Art Colony, known for its artistic vibe and stunning coastal views. Rentals here often boast unique architectural details and artistic decor, with outdoor spaces for relaxing and enjoying the surroundings. Visitors can also take advantage of nearby hiking trails and scenic spots great for nature walks.
What is the most popular type of vacation rental accomodation in Gloucester?
In Gloucester, vacation houses are the most popular type of rental, with around 140 options available throughout the area. These homes often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and ample outdoor space, making them ideal for families or larger groups looking to enjoy the coastal scenery. Many are located near the waterfront, providing easy access to local attractions such as Fishermen's Wharf and the beautiful beaches along the Cape Ann coastline. Additionally, there are approximately 33 apartments and about 15 cottages available, offering a variety of choices for travelers seeking a more intimate or unique stay. Condos are also available, although in fewer numbers, providing another option for those looking to experience Gloucester's charm.
Are there any family house rentals in Gloucester?
In Gloucester, Massachusetts, there is a robust selection of family-friendly house rentals, with around 130 options available throughout the area. Visitors can find properties in charming neighborhoods like East Gloucester and Lanesville, both of which offer easy access to stunning beaches and scenic coastal views. Many homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for barbecues or relaxing after a day of exploration.

In East Gloucester, families can enjoy proximity to Good Harbor Beach, where soft sands and gentle waves create an inviting space for children. Meanwhile, Lanesville provides a more tranquil setting, with rentals that often include gardens and outdoor seating areas, ideal for enjoying the fresh sea breeze.
Can I rent a vacation home with a pool or hot tub in Gloucester?
In Gloucester, Massachusetts, there are several vacation homes available for rent that feature pools and hot tubs, providing a great retreat for travelers. The city, located along the scenic coastline, offers properties in charming neighborhoods such as East Gloucester and Annisquam, where you can find beautiful homes with easy access to local beaches and stunning ocean views.

Travelers can expect amenities such as private pools, hot tubs, and spacious outdoor areas ideal for relaxation and entertainment. Many rentals also include fully equipped kitchens, comfortable living spaces, and outdoor patios or decks, allowing guests to enjoy the fresh coastal air. Additionally, the proximity to local attractions, including beaches, parks, and the vibrant downtown area with its shops and restaurants, enhances the overall vacation experience.
Can I find long-stay vacation rentals in Gloucester?
A long-stay vacation rental in Gloucester is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Gloucester?
In Gloucester, there are numerous pet-friendly house rentals available, making it an excellent destination for travelers with furry companions. The area offers a variety of vacation homes, many of which come equipped with amenities such as spacious backyards, outdoor patios, and fully furnished kitchens, ensuring comfort during your stay.

Neighborhoods like East Gloucester and Annisquam feature charming homes that provide easy access to beautiful beaches and scenic coastal views. The nearby Good Harbor Beach is a popular spot for both relaxation and pet-friendly activities, where dogs are allowed during certain hours, allowing you to enjoy the sun and surf together.

Additionally, the area is rich in outdoor spaces, including parks and nature trails, great for walking your pets. Rentals in these neighborhoods often highlight historic architecture and cozy interiors, suiting those looking for both convenience and a touch of local character.
Are there any remote work vacation rentals in Gloucester?
In Gloucester, Massachusetts, there are plenty of remote work vacation rentals available, with around 167 options to choose from. This coastal city is known for its picturesque views and vibrant maritime heritage, making it an appealing destination for those looking to work remotely while enjoying a scenic environment. Many of the properties offer essential amenities such as high-speed Wi-Fi, allowing for seamless connectivity, and comfortable workspaces within the accommodations.

Travelers can expect a variety of rental types, including charming cottages and modern apartments, often featuring cozy living areas, equipped kitchens for meal preparation, and outdoor spaces to relax after a day of work. The proximity to local attractions like the Cape Ann Museum and the beautiful beaches along the Atlantic adds to the appeal, providing opportunities for leisure activities during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Gloucester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Gloucester with parking available—perfect for families or travelers 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 vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals, which is especially convenient for those who prefer home-cooked dining. Many rentals also feature decks or patios, providing outdoor spaces to relax and enjoy the coastal views. Onsite parking is commonly available, making it easier for guests with vehicles to explore the area. Additionally, rentals often come with coffee and tea makers, ensuring that guests can enjoy their favorite morning beverages.
When is the best time to visit Gloucester for a vacation rental?
The best time to visit Gloucester for a vacation rental is during the peak summer season from June to August, with July being particularly popular among travelers. This vibrant period attracts families and outdoor enthusiasts eager to take advantage of the warm weather and enjoy Gloucester's beautiful beaches, scenic coastal views, and rich maritime history.

During these months, visitors can bask in pleasantly warm temperatures, typically ranging from the mid-60s to the low 80s Fahrenheit. This climate is great for outdoor activities such as kayaking, whale watching, and exploring the picturesque downtown filled with shops and local seafood restaurants. The lively option makes it easy to connect with other travelers while enjoying the region's unique charm.

If you're looking for a more budget-friendly option, consider planning your trip in December. Although this is typically considered the low season, Gloucester's winter season offers a cozy atmosphere and a chance to experience holiday festivities, making it a delightful time to visit without the crowds.
How early should I book a Gloucester vacation rental?
Book your Gloucester vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Gloucester, Massachusetts, United States of America?
In Gloucester, Massachusetts, visitors can enjoy a rich maritime heritage and stunning coastal scenery. The historic downtown area features charming shops and eateries, while the iconic Cape Ann Museum showcases local art and history. Nearby, the scenic waterfront offers beautiful views and opportunities for whale watching and fishing excursions.

The picturesque Rocky Neck Art Colony is a must-visit for art lovers, with galleries and studios highlighting local talent. For nature enthusiasts, the nearby Good Harbor Beach provides a lovely spot for sunbathing and beachcombing, while the Annisquam River and its surrounding areas offer excellent hiking and birdwatching opportunities.

Additionally, visitors can explore the famous Gloucester Fishermen's Memorial and take a stroll along the harbor to experience the vibrant fishing culture firsthand.
Can I change or cancel my Gloucester home rental booking on Vrbo?
To find Gloucester vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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