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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

A "Bitt Of Home" In The Heart Of Gloucester. - Gloucester, VA
9.9 90 reviews

A "Bitt Of Home" In The Heart Of Gloucester.

apartment, Gloucester Courthouse
A Bitt of Home is located in Gloucester Courthouse, a short walk from the hospital, restaurants, shops, and local attractions. This apartment consistently receives excellent ratings for location, cleanliness, and overall experience.
This charming two-bedroom rental comfortably accommodates up to four guests. You'll enjoy a fully equipped kitchen with a refrigerator, microwave, and dishwasher, as well as air conditioning, a garden, and parking.
The Bee Goode House On Main Street - Gloucester, VA
9.9 195 reviews

The Bee Goode House On Main Street

apartment, Gloucester Courthouse
The Bee Goode House is a renovated 1950s home located on Gloucester Main Street, overlooking the town's festivals and activities, with the Warehouse boat ramp 1.5 miles away.
This three-bedroom, two-bathroom home accommodates up to six guests and features a game room with a ping pong table, a spacious yard with a grill and fire pit, and a Mid-Century Modern design.
Charming 3-bedroom Villa With Wifi, And  Jaccuzzi , Just Minutes From Yorktown - Gloucester, VA
8.4 5 reviews

Charming 3-bedroom Villa With Wifi, And Jaccuzzi , Just Minutes From Yorktown

cottage, Gloucester Point
This Hayes villa offers comfortable lodging near Gloucester Point, Virginia, minutes from Yorktown's historic sites and attractions, with a marina and boat ramp directly across the street.
This three-bedroom, two-bathroom house sleeps up to ten guests, featuring three queen beds, one full bed, one bunk bed, and a living room sofa; amenities include air conditioning, internet access, and an outdoor shower (with an indoor shower coming soon).
Family-friendly Main St Gloucester Apt W/ Balcony! - Gloucester, VA
9.8 7 reviews

Family-friendly Main St Gloucester Apt W/ Balcony!

apartment, Gloucester Courthouse
This Gloucester Courthouse Main Street apartment, located above a café, offers convenient access to the Gloucester Museum of History and is within 25 miles of Busch Gardens Williamsburg.
The 900-square-foot rental features three bedrooms, one bathroom, sleeps seven, and includes three Smart TVs, a washer/dryer, and a patio overlooking the shared café area.

Best pet friendly Gloucester, VA vacation rentals

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

Freshly Renovated C1900 Farmhouse In Plainview Surrounded By Crop Fields - Gloucester, VA
10 10 reviews

Freshly Renovated C1900 Farmhouse In Plainview Surrounded By Crop Fields

farm, West Point
This Buena Vista farmhouse rental in Middlesex County sits between West Point and Gloucester, providing easy access to the Middlesex County Museum and Gloucester Museum of History.
This 3000-square-foot property boasts four bedrooms, three bathrooms, and accommodates up to ten guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, plus a terrace, air conditioning, and a lovely garden.
Family-friendly Main St Gloucester Apt W/ Balcony! - Gloucester, VA
10 9 reviews

Family-friendly Main St Gloucester Apt W/ Balcony!

apartment, Gloucester Courthouse
This Gloucester Courthouse apartment rental, located directly on Main Street above the Sweet Tooth Café, offers convenient access to local shops, restaurants, and is near museums and Busch Gardens.
The two-bedroom, one-bathroom unit sleeps seven, features a private balcony, shared patio with gas heater and gazebo, three smart TVs with cable, a well-equipped kitchen, washer/dryer, and pet-friendly accommodations (fee applies).
Serenity Farm Equestrian Retreat In Historic Va - Gloucester, VA
10 28 reviews

Serenity Farm Equestrian Retreat In Historic Va

apartment, Gloucester Courthouse
This charming farmhouse rental is situated in historic Gloucester County, Virginia, offering a peaceful retreat just a short drive from Gloucester Courthouse. The property boasts excellent ratings for cleanliness, location, and overall experience.
The farmhouse offers comfortable accommodations for up to six guests, with a private garden and a swimming pool. Enjoy amenities like air conditioning, internet access, and parking, along with the unique opportunity to experience life on a working farm.
Radiant Gloucester House W/ Private Porch! - Gloucester, VA
9.4 33 reviews

Radiant Gloucester House W/ Private Porch!

apartment, Gloucester Courthouse
This newly renovated 1920s vacation rental is located in downtown Gloucester Courthouse, within walking distance of shops, restaurants, and breweries, and a short drive from popular attractions like Beaverdam Park, the Gloucester Museum of History, and Fort Nonsense. It has received excellent user ratings for its comfort and convenience.
This 2-bedroom, 1-bathroom home offers 1190 square feet of space and can comfortably accommodate up to 6 guests. The house features a well-equipped kitchen, a sunroom, a piano, a twin daybed with a trundle, a garden, a patio, and parking, making it perfect for families or groups of friends.

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 4 best rentals with a pool

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.
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.
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.
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.

Best Gloucester, VA vacation rentals with parking

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.
Private Beach & Deck: Bayfront Home In Hayes! - Gloucester, VA
10 44 reviews

Private Beach & Deck: Bayfront Home In Hayes!

apartment, Gloucester Point
This Gloucester Point vacation rental is located just a short drive from Yorktown's American Revolution Museum and offers easy access to other historical attractions. It has received excellent reviews from previous guests.
The three-bedroom home spans 2,100 square feet and comfortably accommodates up to six guests. Enjoy breathtaking bay views, a private beach, modern amenities, and a spacious deck perfect for relaxing and entertaining.
Perfect For Long-term Workers & Short Stayscomfort, Style & Convenience Await! - Gloucester, VA
8.0 23 reviews

Perfect For Long-term Workers & Short Stayscomfort, Style & Convenience Await!

apartment, Gloucester Courthouse
This Gloucester Courthouse apartment is located in a peaceful rural setting, close to the York River and within easy driving distance of Colonial Williamsburg, Jamestown, and Yorktown. It has earned excellent user ratings for its comfort and amenities.
The apartment offers three bedrooms and two bathrooms, comfortably accommodating up to seven guests. It comes equipped with a fully-equipped kitchen, air conditioning, a Jacuzzi, a garden, and parking, making it perfect for families or groups looking for a relaxing and enjoyable stay.
Monthly Discount- Beautiful House, Gloucester Va - Gloucester, VA
10 31 reviews

Monthly Discount- Beautiful House, Gloucester Va

apartment, Deltaville
This newly renovated house is located just off the Piankatank River in Gloucester, Virginia, a short drive from Deltaville and its attractions. It has received excellent guest ratings, making it a popular choice for travelers. The home features three bedrooms and two bathrooms, providing ample space for up to six guests in its 1000 square feet of living space. Guests can enjoy a fully equipped kitchen, a spacious terrace, a private garden, and a convenient parking space.
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