Find short term rentals in Gloucester, VA at the best prices
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Best Short term and Weekly rentals in Gloucester, VA
Gloucester, VA
20/06 – 27/06
$513/nighttotal: $3591 (7 )
Charming 2-bedroom Condo In Pleasant Williamsburg With Wifi, Ac, Fitness Room
2 2
apartment , Williamsburg
This Williamsburg condo, situated in the central Williamsburg district, offers convenient access to attractions such as Jamestown Settlement and Busch Gardens Williamsburg. The two-bedroom, two-bathroom apartment sleeps six, features a private fitness room, and includes amenities such as air conditioning and Wi-Fi.
Gloucester, VA
20/06 – 27/06
$941/nighttotal: $6587 (7 )
1, 2, 3, Or 4-bedroom In Kings Creek Estates, Williamsburg, Va. All Amenities
4 2
apartment , Williamsburg
This Williamsburg property, situated in the Kings Creek Estate, offers convenient access to Jamestown Settlement, located 5 kilometres away, and is also within easy reach of Water Country USA and Busch Gardens Williamsburg. This spacious four-bedroom, five-bathroom apartment sleeps sixteen guests and boasts amenities including a swimming pool, jacuzzi, and parking, with flexible rental options from a single bedroom to the entire house, alongside golf privileges at The Golden Horseshoe and Kiskiak Golf Club.
10 1 review
Gloucester, VA
27/06 – 31/08
$2998/nighttotal: $194870 (65 )
Brittany Estate On The River
1 4
apartment , Mathews
This luxurious six-bedroom, six-bathroom house, sleeping up to sixteen guests, is situated on the East River near Mathews, Virginia, a short drive from Gloucester. The property boasts a private pier, large inground pool, and five acres of land, perfect for family gatherings or events, and includes amenities such as Wi-Fi, air conditioning, and ample parking.
9.8 109 reviews
Gloucester, VA
18/08 – 20/08
$874/nighttotal: $1748 (2 )
Severnly Pointe Cottage Waterfront Retreat
1 3
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.
9.9 84 reviews
Gloucester, VA
18/08 – 20/08
$384/nighttotal: $768 (2 )
Cozy Cottage On The North River
1 3
apartment , Gloucester Courthouse
This Gloucester Courthouse holiday home is situated in a peaceful neighbourhood, offering convenient access to a public boat ramp and dock, and is close to Busch Gardens Williamsburg and Colonial Williamsburg (distances unspecified). Sleeping six guests, the self-catering property boasts two bedrooms (a king and twin bunk beds), a bathroom, a fully equipped kitchen including dishwasher, a screened porch, outdoor shower, and a well-equipped shed; nearby attractions offer dining and historical sites.
9.8 6 reviews
Gloucester, VA
27/06 – 31/08
$322/nighttotal: $20930 (65 )
Family-friendly Main St Gloucester Apt W/ Balcony!
2 4
apartment , Gloucester Courthouse
This Gloucester Courthouse apartment, situated on Main Street, offers convenient access to local shops and the Gloucester Museum of History, lying approximately 40km from Busch Gardens Williamsburg and 93km from Richmond. The 84-square-metre self-catering property sleeps seven guests across three bedrooms and one bathroom, boasting a terrace, spa access, parking, and in-unit amenities including three smart TVs, a washer/dryer, and a well-equipped kitchen.
10 18 reviews
Gloucester, VA
18/08 – 20/08
$368/nighttotal: $736 (2 )
Carriage House
1 3
B&B , Gloucester Courthouse
The Carriage House, a fully renovated French-style apartment, is situated on the North River in Gloucester County, Virginia, a 14.5-kilometre drive from Gloucester Courthouse's historic Main Street, offering proximity to local attractions and historical sites including Dixondale Wharf. This one-bedroom, one-bathroom apartment sleeps five guests and features a kitchenette with a microwave and mini-fridge, a private dock, on-site activities such as fishing and kayaking, and access to nearby walking and biking trails.
Gloucester, VA
27/06 – 31/08
$1003/nighttotal: $65195 (65 )
Spacious 4-bedroom Townhome In Peaceful Williamsburg With Ac
4 4
apartment , Williamsburg
This four-bedroom townhome in Williamsburg offers proximity to Jamestown Settlement, Water Country USA, and Busch Gardens Williamsburg, situated within easy reach of Walter J. Zable Stadium at Cary Field and Kaplan Arena. This spacious property accommodates up to 8 guests with four bathrooms, two office spaces featuring sofa beds, and climate control, ensuring a comfortable stay with internet access.
10 37 reviews
Gloucester, VA
18/08 – 20/08
$410/nighttotal: $820 (2 )
Welcome To This Waterfront Home With Amazing Views\n
3 3
apartment , Gloucester Courthouse
This Gloucester Courthouse waterfront apartment, situated near the Ware River, offers breathtaking sunset views and is conveniently located for visiting the Gloucester Museum of History and Yorktown Victory Centre (distances unspecified). The three-bedroom, two-bathroom property sleeps six guests and features an open-plan kitchen, living, and dining area with in-unit laundry facilities; a garden is also available.
9.5 91 reviews
Gloucester, VA
18/08 – 20/08
$497/nighttotal: $994 (2 )
The "Hodge Podge" On Back Creek/north River
1 3
apartment , Gloucester Courthouse
This charming apartment is located in Gloucester Courthouse, just a short distance from the town centre and within easy reach of local attractions. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers. The apartment is a spacious four-bedroom home with three bathrooms, comfortably accommodating up to eleven guests. It features a fully equipped kitchen, a private garden, and a wrap-around porch offering stunning views of the surrounding countryside. Guests can enjoy fishing or crabbing from the dock, explore the gardens, and take advantage of the peaceful surroundings.
Gloucester, VA
27/06 – 31/08
$433/nighttotal: $28145 (65 )
Charming 2-bedroom Condo With Wifi, Fitness Room In Wonderful Williamsburg
2 4
apartment , Williamsburg
This Williamsburg holiday home is conveniently located near Colonial National Historical Park (8 km), Yorktown Beach (26 km), Busch Gardens Williamsburg (8 km), and Water Country USA (6 km), offering easy access to major attractions. This two-bedroom, two-bathroom apartment sleeps six, features a jetted tub, Wi-Fi, air conditioning, and a dryer, and includes essential supplies; nearby activities include Pirate's Cove Adventure Golf and Bounce House.
Gloucester, VA
20/06 – 27/06
$424/nighttotal: $2968 (7 )
Warner Hall
1 2
B&B , Gloucester Point
Warner Hall B&B, situated in Gloucester, offers pet-friendly lodging 9 kilometers from Gloucester city centre, providing a peaceful retreat outside the urban bustle. This Gloucester Point guesthouse features one bathroom, accommodates two guests, and includes free Wi-Fi, on-site parking, and air conditioning.
Best family friendly Gloucester, VA Short term rentals
Among the 14 accommodations in Gloucester, VA, here are the 4 best family friendly rentals
10 26 reviews
Gloucester, VA
20/06 – 27/06
$416/nighttotal: $2912 (7 )
Inn At Warner Hall
1 2
B&B , Gloucester Point
The Inn at Warner Hall is a waterfront guesthouse situated in Gloucester Point, just 24 kilometres from historic Yorktown and 56 kilometres from Colonial Williamsburg. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience. The guesthouse is set on a 40-acre estate dating back to 1642, offering a unique glimpse into the region's history. Guests can enjoy a daily gourmet breakfast, relax in the gardens or on the porch, and take advantage of the boathouse for fishing or birdwatching.
9.8 30 reviews
Gloucester, VA
18/08 – 20/08
$327/nighttotal: $654 (2 )
Renhaven Cottage
1 3
apartment , Gloucester Courthouse
This apartment is located in Gloucester Courthouse, Virginia, offering stunning views of the North River and easy access to the waterfront. It consistently receives excellent ratings for its cleanliness, location, and overall experience. The self-catering accommodation sleeps four guests and features two bedrooms, one with a king-size bed and the other with a queen-size bed. Guests can enjoy a private dock, kayak launch, outdoor patio with a gas grill, and a fully equipped kitchen.
8.0 20 reviews
Gloucester, VA
18/08 – 20/08
$403/nighttotal: $806 (2 )
Perfect For Long-term Workers & Short Stayscomfort, Style & Convenience Await!
3 3
apartment , Gloucester Courthouse
This charming three-bedroom property is situated in Gloucester, a peaceful rural area just a short drive from the York River and within easy reach of historical attractions like Colonial Williamsburg, Jamestown, and Yorktown. The apartment has received excellent ratings from previous guests, highlighting its comfortable and welcoming atmosphere. This home provides ample space for up to seven guests, offering a relaxing retreat with two bathrooms and a fully equipped kitchen. Guests can enjoy a range of amenities including air conditioning, a jacuzzi, a garden, parking, and access to the internet, as well as the opportunity to explore the nearby attractions and enjoy water activities on the York River.
9.3 70 reviews
Gloucester, VA
18/08 – 20/08
$2007/nighttotal: $4014 (2 )
Waterfront Sunsets With Pickleball Court & Hot Tub
9 3
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.
Best Gloucester, VA lodging with a balcony
9.5 2 reviews
Gloucester, VA
20/06 – 27/06
$370/nighttotal: $2590 (7 )
Family-friendly Main St Gloucester Apt W/ Balcony!
2 2
apartment , Gloucester Courthouse
This Gloucester Courthouse apartment, situated in Gloucester, Virginia, offers easy access to Busch Gardens Williamsburg, Water Country USA, and Colonial Williamsburg, all within 42-44km. The 84-square-metre property features two bedrooms, one bathroom, sleeps thirteen guests, and includes a fully equipped kitchen, private balcony, on-site parking, and a spa; in-unit laundry facilities add further convenience.
Gloucester, VA
27/06 – 31/08
$544/nighttotal: $35360 (65 )
Charming 3-bedroom Townhome In The Sought After Estates In Williamsburg.\nno Pets
3 4
apartment , Williamsburg
This townhome in Williamsburg offers immediate access to Water Country USA and is situated 7.2 kilometres from Busch Gardens Williamsburg, with Jamestown Settlement also a short drive away. This spacious 3-bedroom accommodation, capable of hosting 10 guests, features two kitchens, a jetted bathtub, and on-site recreational facilities including a fitness centre and game room, making it ideal for exploring local attractions and theme parks.
8.0 1 review
Gloucester, VA
18/08 – 20/08
$485/nighttotal: $970 (2 )
Family-friendly Main St Gloucester Apt W/ Balcony!
1 3
apartment , Gloucester Courthouse
This Gloucester Courthouse apartment is conveniently located near the Gloucester Museum of History and Fairfield Foundation (under 1.6km), and Main Street Centre and Gloucester Public Library (within 2.4km). The self-catering flat offers a fully equipped kitchen, private balcony, free WiFi, free parking, and an in-apartment fireplace; nearby attractions include the museum and library.
Gloucester, VA
27/06 – 31/08
$727/nighttotal: $47255 (65 )
Spacious 3-bedroom Estate With Ac In Delightful Williamsburg
3 4
apartment , Williamsburg
This three-bedroom residence in Williamsburg offers convenient access to historical sites such as Jamestown Settlement, located approximately 5 kilometres away, and entertainment venues like Water Country USA and Busch Gardens Williamsburg. This spacious abode accommodates up to seven guests with three bedrooms, three bathrooms (one with a jetted tub), and a dedicated office space with a sofa bed, featuring air conditioning, Wi-Fi, a swimming pool, jacuzzi, terrace, garden, and parking.
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?
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
9.9 31 reviews
Gloucester, VA
18/08 – 20/08
$553/nighttotal: $1106 (2 )
Bill's Island
1 3
cabin , Gloucester Courthouse
This delightful Ware Neck, Gloucester County retreat overlooks Elmington Creek and the North River, offering easy access to Gloucester Courthouse's shops and historical sites (exact distance requires further research). The two-bedroom, two-bathroom lodge sleeps four, boasting a private dock, serene creek views, and modern amenities including Wi-Fi, air conditioning, and a fully equipped kitchen.
10 3 reviews
Gloucester, VA
20/06 – 27/06
$462/nighttotal: $3234 (7 )
East River Views - Renovated 1905 House- 3 Bedrooms, 3.5 Baths
3 2
apartment , Mathews
This three-bedroom, three-and-a-half-bathroom apartment in Westville, Mathews County, boasts a riverfront location offering tranquil views and is a short drive (approximately 35km) from the Gwynn's Island Museum and Ware Parish Church. The 223 square metre self-catering property sleeps six, includes a fully equipped kitchen, in-unit laundry, air conditioning, Wi-Fi, a terrace, and garden, with nearby opportunities for wildlife viewing and water sports.
10 1 review
Gloucester, VA
20/06 – 27/06
$893/nighttotal: $6251 (7 )
Charming Riverside Cottage W/optional Guest House
4 2
apartment , Deltaville
This renovated 1774 farmhouse, situated on the Piankatank River in Piankatank, Virginia, offers direct riverfront access with a private sandy beach, and is less than 0.2 km from Deltaville's Main Street and the Deltaville Maritime Museum. This four-bedroom, two-bathroom property sleeps up to 14 guests, boasting a fully equipped kitchen, multiple outdoor spaces including a deck, patio with fire pit and private dock, plus kayaks, life jackets and other beach equipment for use.
10 82 reviews
Gloucester, VA
18/08 – 20/08
$345/nighttotal: $690 (2 )
A "Bitt Of Home" In The Heart Of Gloucester.
1 3
apartment , Gloucester Courthouse
This charming two-bedroom flat is situated in Gloucester Courthouse, less than a mile from the local hospital and within easy reach of restaurants, shops, and entertainment venues. Guests consistently rate this property highly for its excellent location, cleanliness, and overall experience. The flat is ideal for families or groups of up to four, offering a comfortable and well-equipped space. Amenities include a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and parking.
Best Gloucester, VA lodging with laundry available
Gloucester, VA
20/06 – 27/06
$457/nighttotal: $3199 (7 )
Kings Creek Rental Dec. 19th-26th 2025 Sleeps 6, 3bds. Minutes From Bush Gardens
3 2
apartment , Williamsburg
This 3-bedroom, 2-bathroom apartment is located in the King's Creek gated community in Williamsburg, offering easy access to attractions such as Busch Gardens Williamsburg, just 1.6 kilometres away, and Water Country USA, also a short drive. This 102 square metre holiday let accommodates up to 6 guests and features a full kitchen, in-unit laundry, a sunroom, and access to community amenities including swimming pools, saunas, a gym, and tennis courts.
9.9 381 reviews
Gloucester, VA
18/08 – 20/08
$270/nighttotal: $540 (2 )
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
2 3
apartment , Gloucester Courthouse
This family-friendly holiday home is located in a peaceful rural setting, just 11 kilometres from Gloucester Museum of History and 13 kilometres from Riverside Walter Reed Hospital. The property has received excellent ratings for its cleanliness, location, and overall experience. The spacious 93 square metre property can comfortably accommodate up to four guests in its two bedrooms and one bathroom. The house offers a range of amenities and features including a swimming pool, jacuzzi, terrace, garden, spa, parking, and a fully equipped kitchen, providing everything you need for a relaxing and enjoyable stay.
9.7 69 reviews
Gloucester, VA
18/08 – 20/08
$412/nighttotal: $824 (2 )
Radiant Gloucester House W/ Private Porch!
2 3
apartment , Gloucester Courthouse
This renovated 1920s property is located in downtown Gloucester Courthouse, Virginia, within walking distance of local shops and restaurants, and a short drive (approximately 60km) from Colonial Williamsburg and Busch Gardens. This two-bedroom, one-bathroom house sleeps six guests and offers keyless entry, free Wi-Fi, a well-equipped kitchen with modern appliances, a washer/dryer, a sunroom, and a garden; plus, it's pet-friendly (charges apply).
9.8 12 reviews
Gloucester, VA
20/06 – 27/06
$352/nighttotal: $2464 (7 )
Country Side Living
1 2
cabin , Gloucester Courthouse
This Gloucester Courthouse house, ideal for a peaceful getaway or remote work, offers a secluded location, its precise distance from local attractions unspecified but described as quiet and away from neighbours. The self-catering property features one bedroom, one bathroom, sleeps two, includes a fully equipped kitchen (minus a dishwasher), in-unit laundry, and a dedicated computer room with internet access throughout the dwelling.