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Gloucester, VA vacation rentals
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Best Vacation rentals and Airbnb offers in Gloucester, VA

Best family friendly Gloucester, VA vacation rentals

Among the 23 accommodations in Gloucester, VA, here are the 4 best family friendly rentals

Peaceful 5br Deltaville Stay | Private Dock - Gloucester, VA
No reviews

Peaceful 5br Deltaville Stay | Private Dock

apartment, Deltaville
This waterfront rental in Deltaville offers direct access to Jackson Creek, leading to the Piankatank River and Chesapeake Bay, with Holly Point Nature Park nearby.
This 5-bedroom, 3-bathroom house and guest cottage accommodates 10 guests and includes kayaks, floats, bikes, a private dock, a screened porch, and a gazebo, with a coffee bar and new appliances in the kitchen.
Celebrate The 250th Where It All Started! - Gloucester, VA
9.9 66 reviews

Celebrate The 250th Where It All Started!

apartment, Gloucester Point
This vacation rental is located on St. Brendan's Point, near Yorktown, with Williamsburg and Jamestown about half an hour away, offering easy access to historical landmarks and a peaceful setting. The property has received excellent ratings for location, cleanliness, and overall experience.
The home has four bedrooms and six bathrooms, comfortably accommodating up to ten guests. It features a private beach with water views, a spacious living area, a large deck, and multiple levels with an elevator for easy access. Guests can enjoy kayaking, fishing, swimming, and other outdoor activities, along with amenities like a fire pit, grill, and volleyball net.
Severnly Pointe Cottage Waterfront Retreat - Gloucester, VA
9.8 111 reviews

Severnly Pointe Cottage Waterfront Retreat

apartment, Gloucester Point
This charming river cottage is located on Free School Creek, just off the Mobjack Bay, a short boat ride from Gloucester Point. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This waterfront cottage offers a spacious layout, accommodating up to 9 guests. Enjoy stunning views, a private dock, a boat launch, a fishing cleaning station, and modern amenities for a relaxing and memorable stay.
Great Wolf Lodge Williamsburg - Gloucester, VA
8.8 1004 reviews

Great Wolf Lodge Williamsburg

resort, Williamsburg
Great Wolf Lodge Williamsburg is located in a rural area of Williamsburg, just a short distance from attractions like MagiQuest, Sentara Williamsburg Regional Medical Center, and Swing Kingz. The hotel consistently receives high ratings for its location, cleanliness, and overall experience.
The lodge features a variety of amenities, including multiple indoor pools, a water park, and a fitness center. Guests can also enjoy dining options like restaurants, bars, and cafes, as well as spa services and room service.

Best pet friendly Gloucester, VA vacation rentals

Among the 23 accommodations in Gloucester, VA, here are the 4 best pet friendly rentals

Beautiful & Peaceful House Overlooking The River. Pets Welcome! Kayaks And Dock - Gloucester, VA
10 27 reviews

Beautiful & Peaceful House Overlooking The River. Pets Welcome! Kayaks And Dock

apartment, Gloucester Courthouse
This Gloucester Courthouse vacation home sits right on the river, offering beautiful views and easy access to a sandy beach and a dock with kayak launch. It's also a short drive to the Gloucester Museum of History and the Yorktown Victory Center. Guests have consistently rated this property excellent.
The 2,200 square foot home has 3 bedrooms, 3 bathrooms, and can accommodate up to 10 guests. It features a modern kitchen, a spacious living area, a private balcony, a screened porch, a deck, and a variety of entertainment options for all ages, including outdoor games and a bunk room.
Waterfront Sunsets With Pickleball Court & Hot Tub - Gloucester, VA
9.1 73 reviews

Waterfront Sunsets With Pickleball Court & Hot Tub

apartment, Gloucester Courthouse
This luxurious waterfront estate near Gloucester Courthouse, Virginia, offers easy access to Gloucester City (15 minutes), Yorktown Beach (50 minutes), and Williamsburg (55 minutes).
This nine-bedroom, seven-bathroom house sleeps up to 16 guests (with additional fees for more), boasting a private pickleball court, hot tub, arcade, mini-golf, movie area, a separate guest suite, and a floating dock for boating, fishing, and kayaking.
Water Front Oasis With Pickle-ball Court And Hot Tub - Gloucester, VA
8.8 13 reviews

Water Front Oasis With Pickle-ball Court And Hot Tub

apartment, Gloucester Courthouse
This waterfront rental is conveniently located in North Gloucester Courthouse, close to beautiful natural areas like Bethel Beach Natural Area Preserve and Middle Peninsula State Park. It's also within easy reach of Deltaville Maritime Museum and Busch Gardens Williamsburg. The apartment has received excellent user ratings, making it a popular choice for travelers.
This spacious home features 9 bedrooms and 7 bathrooms, comfortably accommodating up to 24 guests. A detached guest suite with its own kitchen and bedrooms offers extra privacy. The apartment is equipped with a variety of amenities, including a private pickleball court, a hot tub, an arcade, a movie theater, and a private dock for fishing and kayaking.
Old Log Cabin School House W/10 Acres On The Bay - Gloucester, VA
9.6 100 reviews

Old Log Cabin School House W/10 Acres On The Bay

apartment, Mathews
This Mathews County, Virginia waterfront vacation home boasts stunning Chesapeake Bay views and direct water access from its private 10-acre peninsula location, just 5 minutes from a marina and 15 minutes from larger beaches.
The 4-bedroom, 2-bathroom log cabin sleeps 11 guests and features a private dock with kayaks and canoes, a screened porch, a 55" HD TV, an 8-burner gas stove, a jacuzzi, and ample outdoor amenities including a private beach, fire pit, and walking trails.

Frequently Asked Questions about vacation rentals in Gloucester, VA

  • What are the must-see sights in Gloucester, Virginia?

    For must-see sights in Gloucester, Virginia, you should definitely check out the historic courthouse, a beautiful example of architecture from the early 1900s. Also, the Gloucester Point Lighthouse offers stunning views of the York River. Don't miss the picturesque waterfront areas along the York River, perfect for relaxing strolls.
  • What are the best Airbnb and vacation rentals in Gloucester, VA?

    The Bee Goode House On Main Street, Right On Main St Shops - Arts - Dining And More and Cozy Gloucester Getaway With Porch And Sunroom are the most popular Airbnb and vacation rentals in Gloucester, VA among travelers.

  • Are there unique natural phenomena in Gloucester, Virginia?

    Gloucester's location on the York River provides beautiful natural scenery. The tidal marshes are teeming with wildlife, and the river itself offers opportunities for birdwatching and exploring the varied ecosystems. The sunsets over the York River are particularly spectacular.
  • What are the most popular Airbnbs in Gloucester, VA?

  • What essentials should you bring along for a trip to Gloucester, Virginia?

    Pack comfortable walking shoes, as you'll likely be doing a fair bit of exploring on foot. Sunscreen and a hat are a must, especially during the warmer months. Insect repellent is also recommended, particularly if you plan on spending time outdoors near the marshes. Don't forget your camera to capture the beautiful scenery!
  • What are the best vacation rentals with a pool in Gloucester, VA?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Gloucester, Virginia?

    A daily budget of $150-$300 per person should cover a comfortable stay in Gloucester, Virginia. This estimate includes mid-range accommodation, meals at local restaurants, some activity costs, and local transportation. Budget travelers might find options for less, while those seeking luxury accommodations and experiences will likely spend more.
  • What are the best rentals for families and kids in Gloucester, VA?

  • Where can you find the best restaurants serving local dishes in Gloucester, Virginia, and what are the must-try specialties?

    Unfortunately, there isn't a definitive list of restaurants specifically known for serving unique Gloucester specialties. However, several local restaurants offer fresh seafood dishes, which are common in the area. It's best to explore the local dining options and see what piques your interest. Many restaurants feature seasonal menus, so be sure to check what's fresh and available during your visit.
  • What are some less-famous attractions in Gloucester, Virginia that are worth the visit?

    While not widely known, exploring the various creeks and inlets around Gloucester Point by kayak or boat can be a rewarding experience. Many quieter, less-visited areas offer beautiful views and opportunities for wildlife spotting. The smaller, local parks offer peaceful spots for picnics and relaxation.
  • What are the best activities for engaging with locals and understanding their culture in Gloucester, Virginia?

    Visiting local farmers' markets is a great way to interact with residents and learn about the area's agricultural heritage. Striking up conversations with staff at local shops and restaurants can offer insights into daily life in Gloucester. Attending any local events or festivals happening during your visit could provide opportunities for cultural exchange.
  • What unique natural landscapes and terrain features can travelers explore in Gloucester, Virginia?

    Gloucester boasts the scenic York River shoreline, featuring tidal marshes, creeks, and diverse wildlife habitats. The relatively flat terrain makes it easy to explore on foot or by bike. The river itself offers opportunities for boating, kayaking, and fishing, allowing visitors to experience the natural beauty from the water.
  • How many days are ideal for visiting Gloucester, Virginia, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Gloucester. A possible itinerary could include a day exploring the historic downtown area and waterfront, a day dedicated to outdoor activities like kayaking or visiting the lighthouse, and a day for relaxation and exploring local restaurants. Adjust this based on your interests and available time.
  • How is the weather in Gloucester, Virginia in high season?

    Gloucester's high season is during the summer months (June-August), with warm temperatures and high humidity. Expect average highs in the 80s°F (around 27°C) and average lows in the 60s°F (around 16°C). Be prepared for occasional rain showers, so pack accordingly. Spring and fall offer milder temperatures and fewer crowds.

Nearby regions

Best Gloucester, VA vacation rentals with a pool

Among the 23 accommodations in Gloucester, VA, here are the 1 best rentals with a pool

Patriots Inn - Gloucester, VA
9.2 1966 reviews

Patriots Inn

resort, Williamsburg
Patriots Inn is located in Williamsburg, just a short drive from the College of William & Mary and Colonial Williamsburg. The resort boasts excellent user, location, and cleanliness ratings, making it a top choice for travelers. The hotel offers comfortable rooms with private bathrooms and amenities like air conditioning, a TV, and free Wi-Fi. Guests can enjoy a swimming pool, a Jacuzzi, a fitness center, and a garden for relaxation and recreation.

Best Gloucester, VA vacation rentals with parking

Little Oakland Farm - Gloucester, VA
9.6 5 reviews

Little Oakland Farm

apartment, Mathews
This Mathews County cottage, situated on Oakland Creek near Mobjack Bay Marina, offers easy access to both Mathews (15 minutes) and Gloucester (20 minutes) Courthouses for dining and shopping.
This four-bedroom, two-bathroom rental sleeps up to ten guests and includes two kayaks, two paddleboards, a screened porch, and board games, plus access to a private dock.
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