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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

Lazy Day Getaway In Mathews - Gloucester, VA
9.6 42 reviews

Lazy Day Getaway In Mathews

apartment, Gloucester Courthouse
This waterfront rental is situated in a peaceful neighborhood in Gloucester Courthouse, just a short walk from the North River and a community dock. The apartment consistently receives excellent ratings for location, user experience, and cleanliness, ensuring a comfortable and enjoyable stay.
The spacious home features four bedrooms and three bathrooms, comfortably accommodating up to eight guests. Enjoy amenities like a fully equipped kitchen, air conditioning, a private deck and balcony, and access to a community dock for water activities.
Cottage On A Private Island In The York River - Gloucester, VA
10 381 reviews

Cottage On A Private Island In The York River

cottage, Gloucester Point
This waterfront cottage in Gloucester Point is conveniently located within 9 miles of popular attractions like Machicomoco State Park, Yorktown Beach, and Yorktown Farmers Market, making it a great base for exploring the area. The property has earned excellent user ratings, suggesting a high level of satisfaction among previous guests.
The 1500 square foot cottage comfortably sleeps up to 8 guests in its 3 bedrooms. Enjoy amenities like a private pool, a spa, a terrace, and a fully equipped kitchen, along with access to a garden, a barbecue grill, and a water park.
Waterfront Sunsets With Pickleball Court & Hot Tub - Gloucester, VA
9.1 76 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.
Renhaven Cottage - Gloucester, VA
9.9 41 reviews

Renhaven Cottage

apartment, Gloucester Courthouse
This Gloucester Courthouse apartment overlooks the North River, just a short distance from the historic downtown area, offering easy access to shops, restaurants, and attractions. It has consistently earned excellent ratings for its cleanliness, location, and overall experience.
The apartment features two bedrooms, accommodating up to four guests, and includes a fully equipped kitchen, washer/dryer, and comfortable living spaces. Enjoy stunning river views from the living room, master bedroom, and deck, and take advantage of the private dock, kayak access, and outdoor patio with a gas grill.

Best pet friendly Gloucester, VA vacation rentals

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

Charming 2-bedroom Estate In Beautiful Williamsburg With Wifi, Fitness Room - Gloucester, VA
9.0 2 reviews

Charming 2-bedroom Estate In Beautiful Williamsburg With Wifi, Fitness Room

apartment, Williamsburg
This Williamsburg apartment rental is centrally located, offering easy access to Jamestown Settlement, Busch Gardens Williamsburg, and Water Country USA, though precise distances are not specified.
The two-bedroom, two-bathroom unit sleeps six, features a queen bed, jetted tub, and in-unit WiFi, plus access to a fitness room; it's conveniently situated near Walter J. Zable Stadium at Cary Field and Kaplan Arena.
Nice 3-bedroom House With Ac In Peaceful Hartfield - Gloucester, VA
No reviews

Nice 3-bedroom House With Ac In Peaceful Hartfield

apartment, Saluda
This Pine Top vacation home is located a short drive from Deltaville's maritime attractions and marinas, with Holyhead Maritime of Deltaville just 19 miles away and Deltaville Marina 20 miles away.
This 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a fully equipped kitchen with a stove, oven, refrigerator, coffee maker, ice maker, and microwave, plus free Wi-Fi, a smart TV, on-site laundry facilities, and air conditioning.
Restored 1930s Cottage On 1 Acre W/ Fire Pit - Gloucester, VA
9.5 190 reviews

Restored 1930s Cottage On 1 Acre W/ Fire Pit

house, Gloucester Point
This charming 2-bedroom cottage is located in Hayes, Virginia, just a short drive from popular attractions like Busch Gardens and Colonial Williamsburg. The house has earned excellent ratings for its cleanliness, location, and overall experience.
This 900-square-foot home comfortably sleeps up to 6 guests and features a fully equipped kitchen, air conditioning, a spacious garden, a relaxing spa, and a fire pit for evenings under the stars. Enjoy scenic river views, explore the 1-acre property, and relax in the peaceful setting of this historic cottage.
Inn At Sandy Creek - Gloucester, VA
10 26 reviews

Inn At Sandy Creek

apartment, Gloucester Courthouse
This peaceful apartment is located in Gloucester County, Virginia, just minutes from Gloucester Courthouse and the Piankatank River. It offers a tranquil setting with a poolside view and has excellent ratings for location, cleanliness, and user experience.
The two-bedroom rental has a private entrance, living space, and outdoor patio, accommodating up to four guests. Enjoy the on-site pool, hot tub, and shared common areas, plus a well-equipped kitchen, laundry facilities, and pet-friendly accommodations.

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?

    The best vacation rental with a pool in Gloucester, VA is Rentoudu - Lataa Ja Nauti ... Lähellä Williamsburg Walk To Ravintoloita Ja Kauppoja.

  • 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 4 best rentals with a pool

Squeaky Shores Gloucester, Va Waterfront York River Oasis - Gloucester, VA
9.2 17 reviews

Squeaky Shores Gloucester, Va Waterfront York River Oasis

apartment, Gloucester Courthouse
This Gloucester Courthouse apartment is just a short drive from Williamsburg Premium Outlets and offers stunning views of the York River, creating a peaceful and relaxing atmosphere. The apartment has earned an excellent user rating, making it a popular choice for travelers seeking a comfortable and enjoyable stay.
This spacious home features 5 bedrooms and 4 bathrooms, accommodating up to 10 guests. Enjoy the private pool, a terrace with river views, a garden, a sauna, and a kitchen equipped with a fridge, microwave, and dishwasher.
Cozy 1-bedroom Apartment With Ac In Serene Williamsburg - Gloucester, VA
No reviews

Cozy 1-bedroom Apartment With Ac In Serene Williamsburg

apartment, Williamsburg
This apartment in Williamsburg is a 4-minute drive to Water Country USA and a 5-minute drive to Colonial National Historical Park, offering convenient access to local attractions.
This 1-bedroom, 1-bathroom condo accommodates up to 4 guests and features a private balcony, air conditioning, complimentary Wi-Fi, a heated pool, and a hot tub.
Clay Bank River Front Cottage - Gloucester, VA
9.9 120 reviews

Clay Bank River Front Cottage

house, Gloucester Courthouse
This waterfront cottage is located just 28 acres outside of Gloucester Courthouse, offering a peaceful escape from the city while being a short drive to historical landmarks like Yorktown, Williamsburg, and Jamestown. The property boasts excellent user, location, and cleanliness ratings, making it a highly recommended choice for travelers.
The cottage features two bedrooms and one bathroom, comfortably accommodating up to six guests. It offers a private pool, kayaks, a fishing and crabbing pier, updated amenities, and a pet-friendly environment.
Eclectic Apartment- 2-4 Friends- Family Centered. Safe Neighborhood - Gloucester, VA
10 6 reviews

Eclectic Apartment- 2-4 Friends- Family Centered. Safe Neighborhood

apartment, Gloucester Courthouse
This Gloucester Courthouse apartment rental is conveniently located within 6 miles of the Stifel Conservation Easement, Ark Park, and the Captain John Smith National Historic Trail, and 9 miles from Beaverdam Park.
The one-bedroom, one-bathroom unit sleeps four guests and boasts a private pool, private yard, and access to a smoke-free environment, plus amenities including air conditioning, internet, and parking.

Best Gloucester, VA vacation rentals with parking

3 Bedroom In Williamsburg - Next To Busch Gardens! - Gloucester, VA
9.8 111 reviews

3 Bedroom In Williamsburg - Next To Busch Gardens!

apartment, Williamsburg
This Williamsburg vacation rental is conveniently located within a short drive of Colonial National Historical Park, Queens Lake, and Powell House, making it an ideal base for exploring the city's historical attractions. The property enjoys excellent ratings for location, cleanliness, and overall user experience.
This 3-bedroom, 2-bathroom home comfortably accommodates up to 6 guests. The fully equipped kitchen, outdoor patio, and washer/dryer provide all the conveniences you need for a comfortable and enjoyable stay.
River Vibes Only - Golf Near By - Gloucester, VA
10 6 reviews

River Vibes Only - Golf Near By

apartment, Saluda
This three-bedroom, two-bathroom vacation rental in Hartfield, Virginia, is conveniently located within a 20-30 minute drive of the Urbanna Historic District, White Stone Beach, and the Deltaville Maritime Museum.
The 3-bedroom, 2-bathroom home sleeps eight and includes Wi-Fi, air conditioning, a dryer, and an ironing board; nearby attractions include Piankatank River Golf Club and Holly Point Nature Park.
White Heron Cottage - Gloucester, VA
9.8 261 reviews

White Heron Cottage

apartment, Gloucester Courthouse
This Gloucester Courthouse cottage is conveniently located 15 minutes from Gloucester Courthouse and 45 minutes from Williamsburg, Virginia, offering easy access to nearby public beaches.
The three-bedroom, one-bathroom house sleeps six guests and features a fully equipped kitchen with a dishwasher, in-unit laundry, and a living room with a smart TV; king and queen memory foam mattresses ensure comfortable sleeping.
A Bitt Of Home On Beaver - Gloucester, VA
10 8 reviews

A Bitt Of Home On Beaver

apartment, Gloucester Courthouse
This 3-bedroom, 2-bathroom apartment is centrally located in Gloucester Courthouse, offering a peaceful setting with convenient access to local amenities.
This comfortable dwelling accommodates up to 6 guests and features air conditioning, internet, and a full kitchen, making it ideal for professionals and families needing a functional temporary home.
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