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

Inn At Warner Hall - Gloucester, VA
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.
Renhaven Cottage - Gloucester, VA
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.
Perfect For Long-term Workers & Short Stayscomfort, Style & Convenience Await! - Gloucester, VA
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.
Waterfront Sunsets With Pickleball Court & Hot Tub - Gloucester, VA
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

Family-friendly Main St Gloucester Apt W/ Balcony! - Gloucester, VA
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.
Charming 3-bedroom Townhome In The Sought After Estates In Williamsburg.\nno Pets - Gloucester, VA
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.
Family-friendly Main St Gloucester Apt W/ Balcony! - Gloucester, VA
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.
Spacious 3-bedroom Estate With Ac In Delightful Williamsburg - Gloucester, VA
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?

    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

Bill's Island - Gloucester, VA
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.
East River Views - Renovated 1905 House- 3 Bedrooms, 3.5 Baths - Gloucester, VA
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.
Charming Riverside Cottage W/optional Guest House - Gloucester, VA
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.
A "Bitt Of Home" In The Heart Of Gloucester. - Gloucester, VA
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

Kings Creek Rental Dec. 19th-26th 2025 Sleeps 6, 3bds. Minutes From Bush Gardens - Gloucester, VA
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.
"Bee Haven" Cottage Retreat Near Colonial Williamsburg - Gloucester, VA
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.
Radiant Gloucester House W/ Private Porch! - Gloucester, VA
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).
Country Side Living - Gloucester, VA
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.
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