Gloucester vacation rentals

We found 724 vacation rentals — enter your dates for availability

Discover a selection of 154 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:Dec 26 - Jan 2

Image gallery for Oceanfront Dock Escape ~ Kayaks & Paddleboards

Your waterfront adventure awaits! Dive into endless fun and relaxation with stunning views right at your doorstep!
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Oceanfront Dock Escape ~ Kayaks & Paddleboards

Gloucester, MA

12% off
Price is $788
$5,514 for 7 nights
All fees included
Oceanfront Dock Escape ~ Kayaks & Paddleboards

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Find out more about Gloucester

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:

  • Salem Willows Park (11.8 mi / 19 km)
  • Water Park of New England (15.6 mi / 25.2 km)
  • Appleton Farms Grass Rides (11.1 mi / 17.9 km)
  • Bewitched in Salem (13.2 mi / 21.2 km)
  • The Collection (17.3 mi / 27.9 km)
  • Dogs by Design & Cats Too (11.5 mi / 18.4 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 when booking a vacation rental?
When planning a vacation in Gloucester, Massachusetts, one of the best areas to consider for your rental stay is the Waterfront district. This vibrant neighborhood offers stunning views of the harbor and is conveniently located near some of the city's top attractions. Here, you can easily explore the famous Cape Ann Museum, which showcases the region's rich maritime history and art, as well as the scenic Rocky Neck Art Colony, known for its galleries and artist studios. The Waterfront area typically features a variety of vacation rentals, ranging from cozy cottages to elegant waterfront homes, making it a popular choice for visitors.

Another appealing option is the East Gloucester neighborhood, known for its picturesque beaches and charming coastal atmosphere. Staying here puts you close to Good Harbor Beach, a favorite spot for sunbathing and swimming, and the iconic Annisquam Lighthouse, which offers beautiful vistas and a glimpse into the area's nautical heritage. This neighborhood also has a selection of vacation rentals, often with a more relaxed vibe, superb for families or those looking to unwind by the sea.

Lastly, consider the historic downtown area, where you'll find a blend of local shops, restaurants, and cultural sites. This area is within walking distance to the Gloucester Fishermen's Memorial and the bustling harbor, providing a unique glimpse into the town's fishing heritage.
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, Massachusetts, travelers should explore the areas around Good Harbor Beach and Wingaersheek Beach. Good Harbor Beach is particularly popular for its scenic beauty and soft sandy shores, and you can find a variety of rental properties here, ranging from cozy beach cottages to larger family homes. Many of these rentals come equipped with modern amenities like outdoor decks for sunbathing, barbecue grills for summer cookouts, and fully equipped kitchens, great for preparing meals after a day in the sun.

Wingaersheek Beach is another excellent option, known for its tidal flats and calm waters, making it ideal for families with children. Properties in this area often feature spacious backyards, outdoor showers for rinsing off after the beach, and quick access to the sandy shore. Some rentals may also offer stunning views of the water, along with amenities such as beach gear and parking spaces.

Additionally, the area around Cape Ann offers charming seaside villages and local attractions, including galleries and restaurants serving fresh seafood. Travelers may want to consider properties that provide easy access to the scenic coastal walking paths and parks, where you can enjoy beautiful ocean views and nature walks. Find your rental near the beach in Gloucester.
What is the most popular type of vacation rental accomodation in Gloucester?
In Gloucester, vacation houses are the most popular type of rental accommodation, with around 140 available throughout the city. These homes often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or larger groups. Many also provide outdoor spaces such as decks or gardens, superb for enjoying the coastal views and fresh sea air. Additionally, there are about 38 apartments and a selection of cottages, which typically offer a more compact and cozy setup, often including amenities like kitchens and living areas. Condos are also available, though in smaller numbers.
Are there any family house rentals in Gloucester?
In Gloucester, Massachusetts, there are numerous family-friendly house rentals available—around 138 in total. The city's charming neighborhoods, such as the historic downtown area and the scenic waterfront, provide a delightful backdrop for family vacations. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play or families can gather for barbecues.

Visitors will enjoy amenities like Wi-Fi and laundry facilities, ensuring a comfortable stay. Proximity to local attractions, such as the Gloucester Harbor, the Cape Ann Museum, and various beautiful beaches, makes this destination superb for family outings and exploration. See all family-friendly rentals in Gloucester.
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, making it an attractive destination for travelers seeking relaxation and fun. The city is known for its beautiful coastal scenery and charming New England atmosphere, with rentals often found in neighborhoods such as East Gloucester and Annisquam.

Travelers can expect a variety of amenities in these properties, including private pools, outdoor hot tubs, spacious decks, and well-appointed kitchens, great for enjoying meals together after a day of exploration. Many rentals also offer proximity to the beach, local shops, and seafood restaurants, enhancing the overall experience. Find your rental in Gloucester with a pool or a hot tub.
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, travelers will find a variety of pet-friendly house rentals available, with over 50 options to choose from. Many of these rentals are situated near the scenic coast, offering easy access to beautiful beaches and picturesque views. Properties typically feature amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like patios or decks, great for enjoying the fresh sea air with pets.

The downtown area of Gloucester provides a vibrant atmosphere, with local shops and restaurants that welcome pets, making it easy to enjoy the area with furry companions. Additionally, nearby attractions such as Good Harbor Beach and the Cape Ann Marina offer opportunities for walks and exploration, ensuring that both guests and their pets can enjoy the coastal charm of this Massachusetts town. See all pet-friendly rentals in Gloucester.
Are there any remote work vacation rentals in Gloucester?
In Gloucester, Massachusetts, there are numerous vacation rentals suitable for remote work, with around 163 options available. The city, known for its picturesque harbor and rich maritime history, offers a variety of properties that cater to professionals seeking a productive environment. Many of these rentals feature dedicated office spaces, high-speed Wi-Fi, and comfortable desk setups, ensuring a conducive work atmosphere.

Travelers can expect amenities such as laptop workspaces, ergonomic chairs, and even computer monitors in some properties. Beyond work, Gloucester boasts beautiful coastal scenery, with nearby attractions like Good Harbor Beach and the historic Cape Ann Lighthouse, providing great spots for relaxation after a busy day. 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 typically include WiFi, kitchens equipped with essential cooking appliances, and outdoor patios for enjoying the coastal breeze. Many rentals also feature blenders for preparing smoothies or cocktails, as well as coffee and tea makers to start the day with a warm beverage.
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 season from June to August. This vibrant period is particularly popular in July, when the town comes alive with visitors eager to enjoy its stunning coastal scenery, fresh seafood, and rich maritime history. With warm temperatures typically ranging from the mid-60s to the mid-80s Fahrenheit, the weather is great for outdoor activities such as beach outings, whale watching, and exploring the scenic Cape Ann.

During these summer months, Gloucester offers an abundance of opportunities for sightseeing and adventure, including picturesque harbor views and charming shops in the historic downtown area. The lively atmosphere is enhanced by local festivals and events, making it an ideal time for travelers seeking both relaxation and excitement.

For those looking for a more budget-friendly experience, consider planning your trip in December. While this month falls in the low season, it offers a unique charm, with fewer crowds and a cozy holiday atmosphere.
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?
In Gloucester, Massachusetts, visitors can explore a variety of attractions that highlight the city's rich maritime history and beautiful coastal scenery. The historic downtown area features charming shops and restaurants, with a focus on fresh seafood, and is close to the iconic Cape Ann Museum, which showcases local art and history.

The picturesque Rocky Neck Art Colony offers a vibrant artistic community, with galleries and studios located along the waterfront. Nearby, you can stroll along the scenic Good Harbor Beach, known for its stunning views and soft sandy shores, making it superb for a day of relaxation or beach activities.

Another popular highlight is the Gloucester Fishermen's Memorial, which pays tribute to the city's fishing heritage and provides a scenic spot for photos overlooking the harbor.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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