Vacation rentals near Wingaersheek Beach

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Immerse yourself in the breathtaking beauty of Wingaersheek Beach, where stunning ocean views and gentle waves create an idyllic escape. This family-friendly haven boasts a variety of outdoor adventures, from sunbathing on soft sands to exploring charming local neighborhoods filled with rich history and vibrant culture. Choose from spacious vacation rentals that offer all the comforts of home, ensuring your group can relax and create unforgettable memories together.

Holiday rentals with weekly discounts - Wingaersheek Beach

Showing deals for:Oct 23 - Oct 30

Image gallery for Family Friendly Townhouse 75 steps from Long Beach

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10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Family Friendly Townhouse 75 steps from Long Beach

Gloucester

8% off
Price is $455
$3,185 for 7 nights
All fees included
Family Friendly Townhouse 75 steps from Long Beach

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Find out more about Wingaersheek Beach

Why visit Wingaersheek Beach

  • Stunning Ocean Views: Wingaersheek Beach offers breathtaking vistas of the Atlantic, perfect for relaxation and photography.
  • Family-Friendly Atmosphere: The beach is ideal for families, providing a safe and enjoyable environment for all ages.
  • Rich History: Explore nearby historic houses and learn about Gloucester's maritime heritage.
  • Outdoor Adventures: Engage in beach activities, including swimming, sunbathing, and beachcombing.
  • Charming Local Neighborhoods: Discover friendly communities and local attractions that enhance the beach experience.

Popular types of accommodation around Wingaersheek Beach

Planning a getaway to Wingaersheek Beach? Discover the perfect home base among popular vacation rentals, including private homes, apartments, and condos. Enjoy beach amenities like easy access to stunning sands, as well as nearby hotels for extra convenience. Explore Gloucester, MA vacation rentals that offer a range of available amenities to enhance your stay. Make your beach escape memorable with a comfortable and inviting place to call home.

  • Houses: The top choice for visitors at Wingaersheek Beach, offering spacious accommodations ideal for families or groups seeking a home-like atmosphere.
  • Apartments: A favored option for travelers looking for convenience and comfort, apartments provide a cozy stay with essential amenities.
  • Condos: Popular for their modern features and shared facilities, condos are a great choice for those who want a blend of privacy and community.
  • Cottages: Charming and quaint, cottages offer a delightful retreat, perfect for a peaceful getaway near the beach.
  • House Boats: A unique lodging experience, houseboats give guests the chance to enjoy waterfront living while soaking in scenic views.**

Top attractions near Wingaersheek Beach

Wingaersheek Beach in Gloucester, Massachusetts, offers a delightful blend of outdoor experiences and cultural exploration. Visitors can enjoy the scenic beauty of the beach, discover historic houses, and explore local reserves. Don't miss the chance to take Wingaersheek Beach tours and uncover some of the area's beautiful beaches, ensuring a memorable vacation filled with relaxation and adventure.

  • Good Harbor Beach: A picturesque stretch of sand, just 4 miles from Wingaersheek Beach, Good Harbor Beach is perfect for sunbathing and swimming, offering a relaxed beach vibe with breathtaking views of the ocean.
  • Cape Ann: Located 5 miles away, Cape Ann boasts stunning scenery, rugged coastlines, and charming seaside towns, making it an ideal spot for exploration and enjoying the natural beauty of Massachusetts.
  • Hammond Castle: This enchanting castle, also 5 miles from Wingaersheek Beach, combines culture and romance, featuring beautiful architecture and scenic gardens, perfect for a leisurely stroll or a romantic visit.

Things to do recommended for couples

Wingaersheek Beach offers a perfect romantic getaway for couples. Enjoy a leisurely stroll along the sandy shores, explore the tidal pools, or savor a picnic at sunset. Don't forget to visit local seafood restaurants for a cozy dinner with ocean views, creating unforgettable memories together.

Things to do recommended for families

Families visiting Wingaersheek Beach can enjoy a day of beachcombing, building sandcastles, and exploring tide pools. Nearby, the Cape Ann Museum offers engaging exhibits, while the scenic Gloucester Harbor provides opportunities for whale watching and family-friendly boat tours.

Things to do recommended for groups

Explore the stunning coastline with a group kayak tour, enjoy a beach bonfire at sunset, or participate in a guided nature walk to discover local wildlife. Don’t miss the chance to visit nearby historic sites like the Cape Ann Museum for a taste of local culture.

*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 around Wingaersheek Beach

When planning your trip—whether you’re traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your preferences in the search filters. Here are some helpful booking tips for Vrbo.

  • Traveling to Wingaersheek Beach with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group activities. Luckily, you can easily refine your search to include all of these options and more on Vrbo.
  • Traveling to Wingaersheek Beach with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, 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 Wingaersheek Beach: For many families, a vacation just isn't the same without their furry companions. If that resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly properties offer feeding bowls and beds to ensure that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Wingaersheek Beach: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Wingaersheek Beach

Wingaersheek Beach in Gloucester, Massachusetts, offers a delightful family-friendly atmosphere, perfect for a beach vacation. Enjoy stunning ocean views and explore the charming local neighborhoods, rich in history and friendly people. Nearby attractions include picturesque scenery and historical sites, making it an ideal destination for families seeking relaxation and adventure. Discover the unique blend of coastal beauty and vibrant community that Wingaersheek Beach has to offer.

  • North Shore: Located a mere 0.3 miles from Wingaersheek Beach, North Shore is a vibrant coastal area that embraces outdoor and family experiences. With its stunning beaches and scenic lakes, it’s an ideal destination for families looking to enjoy a day in the sun. The local shopping mall and various shopping centers offer a great blend of retail therapy and local dining options. Visitors can also explore educational opportunities that enhance their beach experience, making North Shore a fantastic choice for those seeking a well-rounded vacation.
  • Annisquam: Just 0.5 miles away from Wingaersheek Beach, Annisquam is a charming neighborhood known for its picturesque scenery and laid-back outdoor activities. This area is perfect for beach lovers and those looking to soak in breathtaking views. Annisquam features an arts center that hosts various cultural events, along with a resort and golf course for those looking to indulge in leisure activities. With its beautiful beaches and the nearby cape, visitors can relish in both relaxation and adventure in this delightful locale.
  • Gloucester: As the city where Wingaersheek Beach is located, Gloucester offers a rich blend of beach, outdoor, and scenic experiences. This historic city is home to vibrant arts and culture, with music concerts and an arts center that showcase local talent. Gloucester’s stunning beaches and family-friendly spots make it a perfect destination for visitors of all ages. The city's proximity to beautiful capes allows for exploration of natural beauty, ensuring a memorable vacation filled with both relaxation and discovery.

Best time to go to Wingaersheek Beach

If you're planning a trip to Wingaersheek Beach, 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 October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.1°F (-0.5°C)Light RainMostly SunnyAverageSlightly 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 SunnyHighSlightly High
July69.6°F (20.9°C)Light RainMostly SunnyHighSlightly High
August69.4°F (20.8°C)Light RainMostly SunnyHighSlightly High
September64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
October55.2°F (12.9°C)Light RainMostly SunnyLowAverage
November45.1°F (7.3°C)Light RainMostly SunnyLowAverage
December37.4°F (3.0°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin saving right away.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform for planning your travels. You can start new trips, continue from where you last stopped, or manage your existing plans all in one place. Your saved or booked properties will be neatly organized under categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best vacation rentals near Wingaersheek Beach?
The best vacation rentals near Wingaersheek Beach are typically located right in Gloucester, Massachusetts. You will find a great selection of properties, primarily private vacation homes and comfortable apartments, many just a short distance from the shore. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties.

Many top-rated rentals feature amenities so you can have a comfortable stay, such as a deck or patio for outdoor enjoyment, and laundry facilities for longer stays. These homes are ideal for families or groups seeking a beach-focused getaway.
Are there any cheap vacation rentals near Wingaersheek Beach?
There are several affordable vacation rentals near Wingaersheek Beach, especially if you are flexible with location and travel dates. Budget-friendly stays typically start around $205 per night. You might find great deals in January and April during the off-season. These rentals often include amenities such as WiFi, toiletries, and self-parking, and can range from cozy apartments to private vacation homes, so you can have a comfortable stay.

To get the best value, consider staying slightly outside major hubs in Gloucester. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Wingaersheek Beach while keeping costs down.
What are the best pet-friendly vacation rentals near Wingaersheek Beach?
There are approximately 69 pet-friendly vacation rentals available near Wingaersheek Beach, primarily private vacation homes and some apartments in Gloucester. These properties often feature amenities such as fully equipped kitchens, Wi-Fi, and comfortable living areas, with many specifically accommodating dogs and cats. Guests can find properties that allow pets in smoking rooms, ensuring a variety of options for their stay.

When searching for the best pet-friendly vacation rentals near Wingaersheek Beach, it is essential to review each property's specific pet policies, including any potential size restrictions or additional fees. Wingaersheek Beach is generally pet-friendly, allowing dogs on leashes during specific hours, offering ample space to roam.
What are the top vacation rentals with pools near Wingaersheek Beach?
Several vacation rentals near Wingaersheek Beach offer access to swimming pools, with options for both private and shared facilities. These properties, primarily private vacation homes and some apartments, are concentrated in the Gloucester area, providing convenient access to the beach. Many of these homes come equipped with full kitchens, Wi-Fi, and outdoor spaces, making them suitable for families and groups seeking a comfortable stay.

When selecting your rental, consider whether a private pool for exclusive use or a shared pool with potential additional amenities like a hot tub better suits your group's needs. For cooler months, guests should look for properties with heated or indoor pool options. Reserving in advance, especially for peak summer dates, is recommended to ensure availability.
What are the best family vacation rentals near Wingaersheek Beach?
There are 121 family-friendly vacation homes near Wingaersheek Beach, primarily private vacation homes and apartments, offering ample space and comfort for groups. These properties often feature multiple bedrooms and bathrooms, full kitchens for meal preparation, and washer/dryers for laundry needs. Many also provide outdoor play areas like yards or patios, and entertainment options such as WiFi and books, ensuring a comfortable stay for all guests.

When selecting the ideal family home, look for properties that offer separate spaces for adults and children, along with practical amenities like a fully equipped kitchen. Staying close to Wingaersheek Beach means less travel time, allowing for more enjoyment of the local attractions.
Are there any luxury vacation rentals near Wingaersheek Beach?
Near Wingaersheek Beach, guests can find several luxury vacation rentals that combine coastal surroundings with modern comfort. These properties often feature amenities such as private pools, heated pools, fireplaces, and private beach access. Many homes also boast lake views and offer services like a private chef.

These homes are ideal for families or larger groups, offering conveniences like air conditioning and entertainment spaces. Many of these top-tier stays are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
How much is a vacation rental near Wingaersheek Beach?
Vacation rentals near Wingaersheek Beach offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around $205 per night, providing an affordable option for those looking to experience the area. Mid-range rentals, including private homes with standard amenities, are generally around $520 per night, offering more space and comfort. For those seeking a more luxurious experience, upscale options can cost $760 or more per night, especially during peak seasons or for properties with premium features.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.
Where should I stay when visiting Wingaersheek Beach?
When planning your stay near Wingaersheek Beach, several areas offer distinct advantages for your vacation rental experience.

The immediate area around Wingaersheek Beach provides properties that are a short walk or drive to the sandy shores, superb for those prioritizing beach access and ocean views. These rentals often feature charming coastal designs.

Another excellent option is the neighborhood of Lanesville. This area offers a more residential feel with properties that provide a peaceful retreat while still being a convenient distance from Wingaersheek Beach. Guests here can enjoy a local community feel.

For those desiring a wider selection of dining and shopping opportunities alongside proximity to the beach, properties in downtown Gloucester are an excellent choice. These homes provide easy access to the city's amenities and are a short drive from Wingaersheek Beach.
What is the cheapest month to stay near Wingaersheek Beach?
The cheapest time to find vacation rentals near Wingaersheek Beach is typically during the late Autumn to early Spring (November to April), excluding any major local holidays. January and April frequently offer the best deals on homes and condos, often providing lower rates compared to the peak summer season. Guests can often find various savings during these months, along with greater availability of properties.
Are there any lakefront vacation rentals near Wingaersheek Beach
Lakefront vacation rentals near Wingaersheek Beach are available, primarily situated along lakes in the surrounding area. These properties are a short drive from Wingaersheek Beach, offering convenient access to water activities such as kayaking, fishing, sailing, motorboating, swimming, paddleboating, tubing, or rafting.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy the water views and peaceful surroundings.
Are there any top beachfront vacation rentals near Wingaersheek Beach
Beachfront vacation rentals near Wingaersheek Beach offer guests direct access to the sand, with many properties boasting ocean-view balconies or being just steps from the water. Properties are often found along Atlantic Avenue and nearby coastal roads, providing a tranquil escape. While the immediate area around Wingaersheek Beach is more quiet, guests can easily reach lively dining, nightlife, and shopping in Gloucester just a short drive away.

Guests can take advantage of amenities such as beach chairs, beach towels, and various water sports equipment for activities like snorkeling and kayaking. Accommodation types range from private vacation homes to apartments, including multi-bedroom units with extra living space, great for families or groups. Many rentals feature water views or direct beachfront access.
Are there any monthly vacation rentals near Wingaersheek Beach?
Vrbo offers excellent options for monthly vacation rentals near Wingaersheek Beach, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer vacation with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Wingaersheek Beach.
Are there any last-minute vacation rentals near Wingaersheek Beach?
Vrbo makes it simple to find last-minute vacation rentals near Wingaersheek Beach that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
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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