Vacation rentals in Pittsville, VA

76 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Pittsville, VA

Renovated , cozy condo overlooking Smith Mountain Lake waits for you! - Pittsville, VA

Renovated , cozy condo overlooking Smith Mountain Lake waits for you!

Condo, Pittsville

Renovated , cozy condo overlooking Smith Mountain Lake waits for you! is a condo in Pittsville, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Renovated , cozy condo overlooking Smith Mountain Lake waits for you!

Renovated , cozy condo overlooking Smith Mountain Lake waits for you! is a condo in Pittsville, with pool 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,058.

From$113/night
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Waterfront Condo with Pool for Romantic Getaways and Fisherman. Pet Friendly! - Pittsville, VA

Waterfront Condo with Pool for Romantic Getaways and Fisherman. Pet Friendly!

Condo, Pittsville

Waterfront Condo with Pool for Romantic Getaways and Fisherman. Pet Friendly! is a condo in Pittsville, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Waterfront Condo with Pool for Romantic Getaways and Fisherman. Pet Friendly!

Waterfront Condo with Pool for Romantic Getaways and Fisherman. Pet Friendly! is a condo in Pittsville, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,218.

From$129/night
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Surfboard-themed Huddleston Studio w/ Beach Access - Pittsville, VA

Surfboard-themed Huddleston Studio w/ Beach Access

Apartment, Pittsville

Surfboard-themed Huddleston Studio w/ Beach Access is a apartment in Pittsville, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Surfboard-themed Huddleston Studio w/ Beach Access

Surfboard-themed Huddleston Studio w/ Beach Access is a apartment in Pittsville, with pool access, easy beach access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,315.

From$150/night
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Romantic condo with beautiful sunset views of Smith Mountain Lake - Pittsville, VA

Romantic condo with beautiful sunset views of Smith Mountain Lake

Condo, Pittsville

Romantic condo with beautiful sunset views of Smith Mountain Lake is a condo in Pittsville, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Romantic condo with beautiful sunset views of Smith Mountain Lake

Romantic condo with beautiful sunset views of Smith Mountain Lake is a condo in Pittsville, with pool 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,440.

From$154/night
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Browse Vacation Rentals with a Pool in Pittsville, VA

Add a pool to the search when you want an easy place to cool off between outings.

Frazier 102, A Fully Restored Historic Home - Pittsville, VA

Frazier 102, A Fully Restored Historic Home

Holiday Home, Pittsville

Frazier 102, A Fully Restored Historic Home is a holiday home in Pittsville, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Frazier 102, A Fully Restored Historic Home

Frazier 102, A Fully Restored Historic Home is a holiday home in Pittsville, with pet-friendly space and pool 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,398.

From$158/night
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Resort Amenities & Beach Access: Huddleston Condo - Pittsville, VA

Resort Amenities & Beach Access: Huddleston Condo

Apartment, Pittsville

Resort Amenities & Beach Access: Huddleston Condo is a apartment in Pittsville, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Resort Amenities & Beach Access: Huddleston Condo

Resort Amenities & Beach Access: Huddleston Condo is a apartment in Pittsville, with pool access, easy beach access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,153.

From$249/night
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Lakeshore Glenn - Spacious home w/shared pool, tennis & basketball courts. - Pittsville, VA

Lakeshore Glenn - Spacious home w/shared pool, tennis & basketball courts.

Holiday Home, Pittsville

Lakeshore Glenn - Spacious home w/shared pool, tennis & basketball courts. is a holiday home in Pittsville, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Lakeshore Glenn - Spacious home w/shared pool, tennis & basketball courts.

Lakeshore Glenn - Spacious home w/shared pool, tennis & basketball courts. is a holiday home in Pittsville, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,203.

From$272/night
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#344 Pointe - 2 Bedroom Lakefront Condo at Mariners SML - Pittsville, VA

#344 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

Apartment, Pittsville

#344 Pointe - 2 Bedroom Lakefront Condo at Mariners SML is a apartment in Pittsville, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About #344 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

#344 Pointe - 2 Bedroom Lakefront Condo at Mariners SML is a apartment in Pittsville, with pool access, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,401.

From$321/night
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Best Pittsville, VA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Comfortable Lakefront Property With Views - Pittsville, VA

Comfortable Lakefront Property With Views

Holiday Home, Pittsville

Comfortable Lakefront Property With Views is a holiday home in Pittsville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Comfortable Lakefront Property With Views

Comfortable Lakefront Property With Views is a holiday home in Pittsville, with 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: hot tub, kitchen, with kitchen, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,923.

From$220/night
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Jewelbox Cottage - Dog-friendly Lakefront Home With Private Dock, Canoe & Sups - Pittsville, VA

Jewelbox Cottage - Dog-friendly Lakefront Home With Private Dock, Canoe & Sups

Cottage, Pittsville

Jewelbox Cottage - Dog-friendly Lakefront Home With Private Dock, Canoe & Sups is a cottage in Pittsville, with pet-friendly space and parking. This stay gives travelers a comfortable base…

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About Jewelbox Cottage - Dog-friendly Lakefront Home With Private Dock, Canoe & Sups

Jewelbox Cottage - Dog-friendly Lakefront Home With Private Dock, Canoe & Sups is a cottage in Pittsville, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,159.

From$298/night
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COMPLETELY RENOVATED home located in Mitchell's Point Marina & RV Park. PET FRIENDLY & FIRE PIT! - Pittsville, VA

COMPLETELY RENOVATED home located in Mitchell's Point Marina & RV Park. PET FRIENDLY & FIRE PIT!

Holiday Home, Pittsville

COMPLETELY RENOVATED home located in Mitchell's Point Marina & RV Park. PET FRIENDLY & FIRE PIT! is a holiday home in Pittsville, with pet-friendly space, parking, and kitchen access. This…

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About COMPLETELY RENOVATED home located in Mitchell's Point Marina & RV Park. PET FRIENDLY & FIRE PIT!

COMPLETELY RENOVATED home located in Mitchell's Point Marina & RV Park. PET FRIENDLY & FIRE PIT! is a holiday home in Pittsville, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,403.

From$301/night
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Mountain View, waterfront, large quiet cove, gentle lot, covered dock & deep H2O - Pittsville, VA

Mountain View, waterfront, large quiet cove, gentle lot, covered dock & deep H2O

Holiday Home, Pittsville

Mountain View, waterfront, large quiet cove, gentle lot, covered dock & deep H2O is a holiday home in Pittsville, with easy beach access, parking, and kitchen access. This stay gives…

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About Mountain View, waterfront, large quiet cove, gentle lot, covered dock & deep H2O

Mountain View, waterfront, large quiet cove, gentle lot, covered dock & deep H2O is a holiday home in Pittsville, with easy beach access, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,098.

From$321/night
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Best Pet-Friendly Vacation Rentals in Pittsville, VA

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

Cozy retreat with lots of room for outdoor activities. - Pittsville, VA

Cozy retreat with lots of room for outdoor activities.

Cabin, Pittsville

Cozy retreat with lots of room for outdoor activities. is a cabin in Pittsville, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Cozy retreat with lots of room for outdoor activities.

Cozy retreat with lots of room for outdoor activities. is a cabin in Pittsville, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,214.

From$125/night
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Dock Sun Point - Lakefront home for easy boating, fishing, private dock & AC/Wifi, Dogs ok! - Pittsville, VA

Dock Sun Point - Lakefront home for easy boating, fishing, private dock & AC/Wifi, Dogs ok!

Holiday Home, Pittsville

Dock Sun Point - Lakefront home for easy boating, fishing, private dock & AC/Wifi, Dogs ok! is a holiday home in Pittsville, with pet-friendly space and kitchen access. This stay gives…

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About Dock Sun Point - Lakefront home for easy boating, fishing, private dock & AC/Wifi, Dogs ok!

Dock Sun Point - Lakefront home for easy boating, fishing, private dock & AC/Wifi, Dogs ok! is a holiday home in Pittsville, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,868.

From$229/night
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3 Bedrooms, 1 Flex Room, 3½ Bathrooms! Golden Mountain Views @ Main Lake - Dog Friendly! - Pittsville, VA

3 Bedrooms, 1 Flex Room, 3½ Bathrooms! Golden Mountain Views @ Main Lake - Dog Friendly!

Holiday Home, Pittsville

3 Bedrooms, 1 Flex Room, 3½ Bathrooms! Golden Mountain Views @ Main Lake - Dog Friendly! is a holiday home in Pittsville, with pet-friendly space, parking, and kitchen access. This stay…

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About 3 Bedrooms, 1 Flex Room, 3½ Bathrooms! Golden Mountain Views @ Main Lake - Dog Friendly!

3 Bedrooms, 1 Flex Room, 3½ Bathrooms! Golden Mountain Views @ Main Lake - Dog Friendly! is a holiday home in Pittsville, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,864.

From$254/night
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This cozy 2-bedroom, 1-bath retreat is wrapped in warm cedar with soaring cathedral ceilings, creating the perfect blend of rustic charm. Enjoy beautiful gardens and breathtaking views of the lake and mountain. - Pittsville, VA

This cozy 2-bedroom, 1-bath retreat is wrapped in warm cedar with soaring cathedral ceilings, creating the perfect blend of rustic charm. Enjoy beautiful gardens and breathtaking views of the lake and mountain.

Cabin, Pittsville

This cozy 2-bedroom, 1-bath retreat is wrapped in warm cedar with soaring cathedral ceilings, creating the perfect blend of rustic charm. Enjoy beautiful gardens and breathtaking views of…

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About This cozy 2-bedroom, 1-bath retreat is wrapped in warm cedar with soaring cathedral ceilings, creating the perfect blend of rustic charm. Enjoy beautiful gardens and breathtaking views of the lake and mountain.

This cozy 2-bedroom, 1-bath retreat is wrapped in warm cedar with soaring cathedral ceilings, creating the perfect blend of rustic charm. Enjoy beautiful gardens and breathtaking views of the lake and mountain. is a cabin in Pittsville, with pet-friendly space, 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,783.

From$287/night
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Best Pittsville, VA vacation rentals with a kitchen

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

Lake Starboard - Lakefront w/ Private Dock & Fire Pit - Pittsville, VA

Lake Starboard - Lakefront w/ Private Dock & Fire Pit

Holiday Home, Pittsville

Lake Starboard - Lakefront w/ Private Dock & Fire Pit is a holiday home in Pittsville, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Lake Starboard - Lakefront w/ Private Dock & Fire Pit

Lake Starboard - Lakefront w/ Private Dock & Fire Pit is a holiday home in Pittsville, with 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,432.

From$298/night
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Orr at Waterways - Great home with powered dock, boat launch, outdoor pool, & beach - Pittsville, VA

Orr at Waterways - Great home with powered dock, boat launch, outdoor pool, & beach

Holiday Home, Pittsville

Orr at Waterways - Great home with powered dock, boat launch, outdoor pool, & beach is a holiday home in Pittsville, with pool access, easy beach access, and kitchen access. This stay gives…

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About Orr at Waterways - Great home with powered dock, boat launch, outdoor pool, & beach

Orr at Waterways - Great home with powered dock, boat launch, outdoor pool, & beach is a holiday home in Pittsville, with pool access, easy beach access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,802.

From$324/night
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Castaway - Family-friendly with a dog in protected cove - Pittsville, VA

Castaway - Family-friendly with a dog in protected cove

Holiday Home, Pittsville

Castaway - Family-friendly with a dog in protected cove is a holiday home in Pittsville, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Castaway - Family-friendly with a dog in protected cove

Castaway - Family-friendly with a dog in protected cove is a holiday home in Pittsville, with pet-friendly space, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,668.

From$335/night
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DOCK RENOVATION COMPLETE! Cozy, Pet Friendly Lakefront Home! Come Visit \"Lake Lure\"! - Pittsville, VA

DOCK RENOVATION COMPLETE! Cozy, Pet Friendly Lakefront Home! Come Visit \"Lake Lure\"!

Holiday Home, Pittsville

DOCK RENOVATION COMPLETE! Cozy, Pet Friendly Lakefront Home! Come Visit \"Lake Lure\"! is a holiday home in Pittsville, with pet-friendly space, parking, and kitchen access. This stay gives…

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About DOCK RENOVATION COMPLETE! Cozy, Pet Friendly Lakefront Home! Come Visit \"Lake Lure\"!

DOCK RENOVATION COMPLETE! Cozy, Pet Friendly Lakefront Home! Come Visit \"Lake Lure\"! is a holiday home in Pittsville, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,820.

From$346/night
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Our Favorite Family-Friendly Vacation Rentals in Pittsville, VA

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

Peaceful Chatham Home w/ Grill & Deck - Pittsville, VA

Peaceful Chatham Home w/ Grill & Deck

Cottage, Pittsville

Peaceful Chatham Home w/ Grill & Deck is a cottage in Pittsville, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Peaceful Chatham Home w/ Grill & Deck

Peaceful Chatham Home w/ Grill & Deck is a cottage in Pittsville, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,705.

From$194/night
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Family retreat at the Lake! Dock the boat, fish, jump, or swim from the dock. - Pittsville, VA

Family retreat at the Lake! Dock the boat, fish, jump, or swim from the dock.

Holiday Home, Pittsville

Family retreat at the Lake! Dock the boat, fish, jump, or swim from the dock. is a holiday home in Pittsville, with pool access, kitchen access, and room for a group. This stay gives…

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About Family retreat at the Lake! Dock the boat, fish, jump, or swim from the dock.

Family retreat at the Lake! Dock the boat, fish, jump, or swim from the dock. is a holiday home in Pittsville, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,542.

From$267/night
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LAKE LIVING AT ITS FINEST. Cozy cottage with wide water and mountain views. - Pittsville, VA

LAKE LIVING AT ITS FINEST. Cozy cottage with wide water and mountain views.

Cottage, Pittsville

LAKE LIVING AT ITS FINEST. Cozy cottage with wide water and mountain views. is a cottage in Pittsville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About LAKE LIVING AT ITS FINEST. Cozy cottage with wide water and mountain views.

LAKE LIVING AT ITS FINEST. Cozy cottage with wide water and mountain views. is a cottage in Pittsville, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,545.

From$272/night
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Dock Sun Point - Lakefront Home for Easy Boating, Fishing, Private Dock & Ac/wifi, Dogs ok! - Pittsville, VA

Dock Sun Point - Lakefront Home for Easy Boating, Fishing, Private Dock & Ac/wifi, Dogs ok!

Holiday Home, Pittsville

Dock Sun Point - Lakefront Home for Easy Boating, Fishing, Private Dock & Ac/wifi, Dogs ok! is a holiday home in Pittsville, with pet-friendly space, parking, and room for a group. This…

Read more

About Dock Sun Point - Lakefront Home for Easy Boating, Fishing, Private Dock & Ac/wifi, Dogs ok!

Dock Sun Point - Lakefront Home for Easy Boating, Fishing, Private Dock & Ac/wifi, Dogs ok! is a holiday home in Pittsville, with pet-friendly space, parking, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,037.

From$274/night
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