Find short term rentals in Gloucester, VA at the best prices

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Gloucester, VA short term rentals
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Best Short term and Weekly rentals in Gloucester, VA

Best family friendly Gloucester, VA Short term rentals

Among the 21 accommodations in Gloucester, VA, here are the 4 best family friendly rentals

Celebrate The 250th Where It All Started! - Gloucester, VA
9.9 66 reviews

Celebrate The 250th Where It All Started!

apartment, Gloucester Point
This four-bedroom house is located in Yorktown, Virginia, just 48 kilometres from Williamsburg and Jamestown, offering stunning water views and a private beach on Mobjack Bay. The property has received excellent ratings for its cleanliness, location, and overall experience.
The house has six bathrooms and can accommodate up to 10 guests. Enjoy a range of amenities, including a basketball court, volleyball net, kayaks, a fire pit, a pool table, and a private beach with breathtaking views.
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 log cabin, situated on a private peninsula, boasts stunning Chesapeake Bay views and is approximately 8 km from a marina and 24 km from larger beaches.
Sleeping up to 11 guests, this four-bedroom, two-bathroom holiday home offers a private dock, kayaks, canoes, and fishing equipment, alongside a spacious interior with modern appliances, multiple 55" HD TVs, and extensive outdoor space including a fire pit and games area.
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 Gloucester Point holiday home is situated near Yorktown, a short drive (approximately 8km) from the Yorktown Victory Center and Gloucester Museum of History, offering easy access to the York River.
Sleeping up to 10 guests, the property features three queen beds, one double bed, and a bunk bed, alongside a spacious living area, two bathrooms (one with an outdoor shower, an indoor shower is coming soon), and Wi-Fi; a marina and boat ramp are directly opposite.
Peaceful 5br Deltaville Stay | Private Dock - Gloucester, VA
No reviews

Peaceful 5br Deltaville Stay | Private Dock

apartment, Deltaville
This five-bedroom, three-bathroom detached house in Deltaville offers a waterfront sanctuary on Jackson Creek, with proximity to the Piankatank River and Chesapeake Bay, and is located at the quiet end of the creek, approximately 3.5 kilometres from the mouth of the Piankatank River. This family-friendly property accommodates up to ten guests and includes amenities such as air conditioning, Wi-Fi, a private dock, kayaks, floats, and adult bikes, alongside a fully equipped kitchen and outdoor living spaces.

Best Gloucester, VA lodging with a balcony

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 waterfront property is situated in Gloucester, just a short drive from the Gloucester Museum of History and Yorktown Victory Center, offering a peaceful retreat with easy access to local attractions. The house has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
This spacious three-bedroom home, covering 204 square metres, comfortably accommodates up to 10 guests. Enjoy a range of amenities including a private dock, kayaks, outdoor games, and a fully equipped kitchen, perfect for a relaxing and enjoyable stay.
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 apartment is located in North, Gloucester Courthouse, Virginia, just a short drive from Bethel Beach Natural Area Preserve and Middle Peninsula State Park. The property has received excellent user ratings, making it a popular choice for travellers.
The apartment offers spacious accommodation with nine bedrooms and seven bathrooms, comfortably sleeping up to 24 guests. Guests can enjoy a range of amenities, including a private pickleball court, hot tub, dock, arcade, movie theatre, and a separate guest suite with its own kitchen, two bedrooms, and bathroom.
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 Gloucester Point holiday home is situated near Yorktown, a short drive (approximately 8km) from the Yorktown Victory Center and Gloucester Museum of History, offering easy access to the York River.
Sleeping up to 10 guests, the property features three queen beds, one double bed, and a bunk bed, alongside a spacious living area, two bathrooms (one with an outdoor shower, an indoor shower is coming soon), and Wi-Fi; a marina and boat ramp are directly opposite.

Frequently Asked Questions about short term rentals in Gloucester, VA

  • Can visitors to Gloucester, Virginia witness any unique natural cycles, like cherry blossom season or autumn colors?

    While Gloucester doesn't have the large-scale cherry blossom displays of Washington D.C., the area does experience beautiful autumn foliage. The trees around York River State Park and other natural areas put on a spectacular show of color in the fall, typically peaking in late October or early November. The timing can vary based on the weather.
  • What are the best short term rentals in Gloucester, VA?

    Among the short term rentals in Gloucester, VA, Historic Cottage On Ware River Estate, Right On Main St Shops - Arts - Dining And More and Elm Grove Farm Guest Cottage are the most popular ones.

  • What are the most meaningful ways to engage with locals and discover the culture in Gloucester, Virginia?

    To connect with the local culture, visit the farmers' markets, often held seasonally. These markets offer a chance to meet local producers and learn about their agricultural practices. Also, explore the local shops and restaurants; engaging with the owners and staff offers a glimpse into the community. Attending local events, if any are scheduled during your visit, can also provide opportunities to interact with residents.
  • What are the best short term rentals with a pool in Gloucester, VA?

  • Are there any distinctive cultural activities or hands-on workshops in Gloucester, Virginia?

    Information on specific hands-on workshops or cultural activities in Gloucester requires checking local event listings closer to your travel dates, as these can vary seasonally. However, exploring the historical sites and engaging with the local community, as mentioned previously, offers a cultural experience.
  • What are the best short term rentals for families and kids in Gloucester, VA?

  • What are some secret spots or hidden treasures to visit in Gloucester, Virginia?

    Some less-traveled spots include exploring the backroads and discovering smaller, less-known historical markers throughout the county. A quiet walk along the York River shoreline, away from the main park areas, can offer a peaceful and secluded experience. The specific locations of these hidden gems are best discovered through exploration and local recommendations.
  • What should not be left out of your suitcase if you are going to Gloucester, Virginia?

    Pack comfortable walking shoes for exploring the historical sites and natural areas. Sunscreen and insect repellent are essential, especially during warmer months. Depending on the time of year, you may need layers of clothing as temperatures can fluctuate. And don't forget your camera to capture the memories.

Nearby regions

Best Gloucester, VA lodging with a kitchen

Horse Haven On The Head Of The East River - Gloucester, VA
10 8 reviews

Horse Haven On The Head Of The East River

apartment, Mathews
This renovated farmhouse in Mathews, Virginia, offers a peaceful retreat approximately 80 kilometres from Busch Gardens Williamsburg, Water Country USA, Jamestown Settlement, and Colonial Williamsburg.
Sleeping up to 10 guests, this four-bedroom, three-bathroom property boasts a spacious layout with multiple dining areas, a well-equipped kitchen including a dishwasher, keyless entry, a garden, air conditioning, and access to the East River for kayaking, plus a barbecue and nearby host family for assistance.
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 Gloucester Point holiday home is situated near Yorktown, a short drive (approximately 8km) from the Yorktown Victory Center and Gloucester Museum of History, offering easy access to the York River.
Sleeping up to 10 guests, the property features three queen beds, one double bed, and a bunk bed, alongside a spacious living area, two bathrooms (one with an outdoor shower, an indoor shower is coming soon), and Wi-Fi; a marina and boat ramp are directly opposite.
Waterfront Sunsets With Pickleball Court & Hot Tub - Gloucester, VA
9.1 73 reviews

Waterfront Sunsets With Pickleball Court & Hot Tub

apartment, Gloucester Courthouse
This waterfront property near Gloucester Courthouse, Virginia, offers easy access to Gloucester City (24km), Yorktown Beach (80km), and Williamsburg (88km), home to Busch Gardens and Water Country USA.
Sleeping up to 16 guests (with additional fees for more), this nine-bedroom, seven-bathroom house boasts a private pickleball court, hot tub, arcade, mini-golf, movie area, a separate guest suite, and private waterfront access for boating, fishing, and kayaking.
Severnly Pointe Cottage Waterfront Retreat - Gloucester, VA
9.8 111 reviews

Severnly Pointe Cottage Waterfront Retreat

apartment, Gloucester Point
This river cottage is located on Free School Creek, just off Mobjack Bay, a short boat ride from the popular fishing spot of Mobjack Bay. It has been rated excellent for location, cleanliness and overall experience by previous guests.
The property offers four bedrooms and two bathrooms, comfortably accommodating up to nine guests. This waterfront home features a private dock, a boat launch, a fishing cleaning station, and a spacious garden, making it perfect for families and groups looking for a relaxing getaway.

Best Gloucester, VA lodging with laundry available

Severnly Pointe Cottage Waterfront Retreat - Gloucester, VA
9.8 111 reviews

Severnly Pointe Cottage Waterfront Retreat

apartment, Gloucester Point
This river cottage is located on Free School Creek, just off Mobjack Bay, a short boat ride from the popular fishing spot of Mobjack Bay. It has been rated excellent for location, cleanliness and overall experience by previous guests.
The property offers four bedrooms and two bathrooms, comfortably accommodating up to nine guests. This waterfront home features a private dock, a boat launch, a fishing cleaning station, and a spacious garden, making it perfect for families and groups looking for a relaxing getaway.
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 log cabin, situated on a private peninsula, boasts stunning Chesapeake Bay views and is approximately 8 km from a marina and 24 km from larger beaches.
Sleeping up to 11 guests, this four-bedroom, two-bathroom holiday home offers a private dock, kayaks, canoes, and fishing equipment, alongside a spacious interior with modern appliances, multiple 55" HD TVs, and extensive outdoor space including a fire pit and games area.
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 waterfront property is situated in Gloucester, just a short drive from the Gloucester Museum of History and Yorktown Victory Center, offering a peaceful retreat with easy access to local attractions. The house has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
This spacious three-bedroom home, covering 204 square metres, comfortably accommodates up to 10 guests. Enjoy a range of amenities including a private dock, kayaks, outdoor games, and a fully equipped kitchen, perfect for a relaxing and enjoyable stay.
Waterfront Sunsets With Pickleball Court & Hot Tub - Gloucester, VA
9.1 73 reviews

Waterfront Sunsets With Pickleball Court & Hot Tub

apartment, Gloucester Courthouse
This waterfront property near Gloucester Courthouse, Virginia, offers easy access to Gloucester City (24km), Yorktown Beach (80km), and Williamsburg (88km), home to Busch Gardens and Water Country USA.
Sleeping up to 16 guests (with additional fees for more), this nine-bedroom, seven-bathroom house boasts a private pickleball court, hot tub, arcade, mini-golf, movie area, a separate guest suite, and private waterfront access for boating, fishing, and kayaking.
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