Vacation rentals in Chester, VA

73 available vacation rental offers

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Best vacation rentals and Airbnb offers in Chester, VA

Charming, Private Abode: Serenity in Hopewell, VA! - Chester, VA

Charming, Private Abode: Serenity in Hopewell, VA!

Holiday Home, Chester

Charming, Private Abode: Serenity in Hopewell, VA! is a holiday home in Chester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Charming, Private Abode: Serenity in Hopewell, VA!

Charming, Private Abode: Serenity in Hopewell, VA! is a holiday home in Chester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and ac.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $884.

From$92/night
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! Cozy Cove near Fort Gregg-Adams: Perfect for 2 ! - Chester, VA

! Cozy Cove near Fort Gregg-Adams: Perfect for 2 !

Apartment, Chester

! Cozy Cove near Fort Gregg-Adams: Perfect for 2 ! is a apartment in Chester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About ! Cozy Cove near Fort Gregg-Adams: Perfect for 2 !

! Cozy Cove near Fort Gregg-Adams: Perfect for 2 ! is a apartment in Chester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and washer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $696.

From$99/night
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The Great Pink Lady with Huge Wrap Around Porch! - Chester, VA

The Great Pink Lady with Huge Wrap Around Porch!

Apartment, Chester

The Great Pink Lady with Huge Wrap Around Porch! is a apartment in Chester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About The Great Pink Lady with Huge Wrap Around Porch!

The Great Pink Lady with Huge Wrap Around Porch! is a apartment in Chester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $937.

From$101/night
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Retro bungalow minutes away from historic Old Towne Petersburg! - Chester, VA

Retro bungalow minutes away from historic Old Towne Petersburg!

Holiday Home, Chester

Retro bungalow minutes away from historic Old Towne Petersburg! is a holiday home in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Retro bungalow minutes away from historic Old Towne Petersburg!

Retro bungalow minutes away from historic Old Towne Petersburg! is a holiday home in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $710.

From$101/night
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Family-friendly vacation rentals in Chester, VA

Plan a trip with stays that give families more room to spread out.

Adorable One Bedroom Cottage~Prime Location~Historic with Upgrades - Chester, VA

Adorable One Bedroom Cottage~Prime Location~Historic with Upgrades

Holiday Home, Chester

Adorable One Bedroom Cottage~Prime Location~Historic with Upgrades is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Adorable One Bedroom Cottage~Prime Location~Historic with Upgrades

Adorable One Bedroom Cottage~Prime Location~Historic with Upgrades is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,306.

From$187/night
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Enjoy Breezes on the James River, 2bdrm-1bath / 15 minutes to downtown Richmond - Chester, VA

Enjoy Breezes on the James River, 2bdrm-1bath / 15 minutes to downtown Richmond

Holiday Home, Chester

Enjoy Breezes on the James River, 2bdrm-1bath / 15 minutes to downtown Richmond is a holiday home in Chester, with kitchen access. This stay gives travelers a comfortable base for exploring…

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About Enjoy Breezes on the James River, 2bdrm-1bath / 15 minutes to downtown Richmond

Enjoy Breezes on the James River, 2bdrm-1bath / 15 minutes to downtown Richmond is a holiday home in Chester, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,413.

From$202/night
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Updated Retreat Near James River & Dtwn Hopewell! - Chester, VA

Updated Retreat Near James River & Dtwn Hopewell!

Cottage, Chester

Updated Retreat Near James River & Dtwn Hopewell! is a cottage in Chester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Updated Retreat Near James River & Dtwn Hopewell!

Updated Retreat Near James River & Dtwn Hopewell! is a cottage in Chester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,925.

From$204/night
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The Divine Cottage: Woodsy Hideaway! - Chester, VA

The Divine Cottage: Woodsy Hideaway!

Holiday Home, Chester

The Divine Cottage: Woodsy Hideaway! is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About The Divine Cottage: Woodsy Hideaway!

The Divine Cottage: Woodsy Hideaway! is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,611.

From$230/night
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Pet-friendly vacation rentals in Chester, VA

Bring your pet along with stays that welcome four-legged travelers.

The Great Pink Lady with Huge Wrap Around Porch! - Chester, VA

The Great Pink Lady with Huge Wrap Around Porch!

Holiday Home, Chester

The Great Pink Lady with Huge Wrap Around Porch! is a holiday home in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About The Great Pink Lady with Huge Wrap Around Porch!

The Great Pink Lady with Huge Wrap Around Porch! is a holiday home in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $902.

From$129/night
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Globetrotters Suite in Historic Richmond w Patio - Chester, VA

Globetrotters Suite in Historic Richmond w Patio

Apartment, Chester

Globetrotters Suite in Historic Richmond w Patio is a apartment in Chester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Globetrotters Suite in Historic Richmond w Patio

Globetrotters Suite in Historic Richmond w Patio is a apartment in Chester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,189.

From$131/night
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Contemporary 3-Bedroom Home with Balcony in RVA - Chester, VA

Contemporary 3-Bedroom Home with Balcony in RVA

Apartment, Chester

Contemporary 3-Bedroom Home with Balcony in RVA is a apartment in Chester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Contemporary 3-Bedroom Home with Balcony in RVA

Contemporary 3-Bedroom Home with Balcony in RVA is a apartment in Chester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,235.

From$133/night
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* Prime Location: 2-BR Oasis with Washer & Dryer * - Chester, VA

* Prime Location: 2-BR Oasis with Washer & Dryer *

Apartment, Chester

* Prime Location: 2-BR Oasis with Washer & Dryer * is a apartment in Chester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About * Prime Location: 2-BR Oasis with Washer & Dryer *

* Prime Location: 2-BR Oasis with Washer & Dryer * is a apartment in Chester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,063.

From$152/night
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Vacation rentals with parking in Chester, VA

Find vacation rentals that make arriving by car easier.

Newly finished basement suite in Midlothian. Very clean and spacious. - Chester, VA

Newly finished basement suite in Midlothian. Very clean and spacious.

Holiday Home, Chester

Newly finished basement suite in Midlothian. Very clean and spacious. is a holiday home in Chester, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Newly finished basement suite in Midlothian. Very clean and spacious.

Newly finished basement suite in Midlothian. Very clean and spacious. is a holiday home in Chester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, washer, and dryer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $879.

From$126/night
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Sophisticated 2BR Speakeasy with Moody Vibes - Chester, VA

Sophisticated 2BR Speakeasy with Moody Vibes

Holiday Home, Chester

Sophisticated 2BR Speakeasy with Moody Vibes is a holiday home in Chester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Sophisticated 2BR Speakeasy with Moody Vibes

Sophisticated 2BR Speakeasy with Moody Vibes is a holiday home in Chester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,049.

From$150/night
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Gnome Sweet Home: Hopewell Hideout! - Chester, VA

Gnome Sweet Home: Hopewell Hideout!

Holiday Home, Chester

Gnome Sweet Home: Hopewell Hideout! is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Gnome Sweet Home: Hopewell Hideout!

Gnome Sweet Home: Hopewell Hideout! is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,283.

From$183/night
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Near Hospitals & Attractions: Richmond Getaway! - Chester, VA

Near Hospitals & Attractions: Richmond Getaway!

Holiday Home, Chester

Near Hospitals & Attractions: Richmond Getaway! is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Near Hospitals & Attractions: Richmond Getaway!

Near Hospitals & Attractions: Richmond Getaway! is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,704.

From$243/night
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Vacation rentals with a kitchen in Chester, VA

Compare stays with kitchen access for longer trips and easier meals.

Globetrotter's Suite in Historic Richmond w/ Patio - Chester, VA

Globetrotter's Suite in Historic Richmond w/ Patio

Apartment, Chester

Globetrotter's Suite in Historic Richmond w/ Patio is a apartment in Chester, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Globetrotter's Suite in Historic Richmond w/ Patio

Globetrotter's Suite in Historic Richmond w/ Patio is a apartment in Chester, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,066.

From$152/night
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Contemporary 3-Bedroom Home with Balcony in RVA - Chester, VA

Contemporary 3-Bedroom Home with Balcony in RVA

Apartment, Chester

Contemporary 3-Bedroom Home with Balcony in RVA is a apartment in Chester, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Contemporary 3-Bedroom Home with Balcony in RVA

Contemporary 3-Bedroom Home with Balcony in RVA is a apartment in Chester, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,099.

From$157/night
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1831 House in Historic Old Towne Petersburg, VA - Chester, VA

1831 House in Historic Old Towne Petersburg, VA

Holiday Home, Chester

1831 House in Historic Old Towne Petersburg, VA is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 1831 House in Historic Old Towne Petersburg, VA

1831 House in Historic Old Towne Petersburg, VA is a holiday home in Chester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,357.

From$194/night
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Near Hospitals & Attractions: Richmond Getaway! - Chester, VA

Near Hospitals & Attractions: Richmond Getaway!

Cottage, Chester

Near Hospitals & Attractions: Richmond Getaway! is a cottage in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Near Hospitals & Attractions: Richmond Getaway!

Near Hospitals & Attractions: Richmond Getaway! is a cottage in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,118.

From$239/night
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