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Pittsville Holiday Rentals

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50 rentals in Pittsville.
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Beautiful waterfront lodge with view of Smith Mountain and private boat dock., holiday rental in Pittsville

Beautiful waterfront lodge with view of Smith Mountain and private boat dock.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stylish Creekside Cabin w/Fire Pit Near Wineries!, holiday rental in Pittsville

Stylish Creekside Cabin w/Fire Pit Near Wineries!

4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Tentrr Signature Site - The Babbling Brook, holiday rental in Pittsville

Tentrr Signature Site - The Babbling Brook

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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A Great Year/Unique Historical log cabin with  private beach, 300 Ft Front, holiday rental in Pittsville

A Great Year/Unique Historical log cabin with private beach, 300 Ft Front

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Fall into the Lake! Enjoy the fire pit and high speed internet, holiday rental in Pittsville

Fall into the Lake! Enjoy the fire pit and high speed internet

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Indoor-outdoor Balcony  All amenities, indoor pool, green fees for golf, holiday rental in Pittsville

Indoor-outdoor Balcony All amenities, indoor pool, green fees for golf

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Book your winter getaway now! Cozy wood burning fireplace! Peaceful and quiet!, holiday rental in Pittsville

Book your winter getaway now! Cozy wood burning fireplace! Peaceful and quiet!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Four seasons balcony, Includes all amenities, an indoor pool, golf green fees., holiday rental in Pittsville

Four seasons balcony, Includes all amenities, an indoor pool, golf green fees.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lap Of Luxury.   SML, holiday rental in Pittsville

Lap Of Luxury. SML

5 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Enjoy coffee while taking in beautiful lake/mountain views from 4 Season Balcony, holiday rental in Pittsville

Enjoy coffee while taking in beautiful lake/mountain views from 4 Season Balcony

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated! Quiet Cove, Hot Tub, Fire Pit, Party Deck, Mountain View, holiday rental in Pittsville

Newly Renovated! Quiet Cove, Hot Tub, Fire Pit, Party Deck, Mountain View

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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December Weekend Getaways Still Available!, holiday rental in Pittsville

December Weekend Getaways Still Available!

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Power down as hot tub, kayaks, and pool table await, holiday rental in Pittsville

Power down as hot tub, kayaks, and pool table await

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Fun Spot 2 - BEST DOCK AND PATIO WITH A VIEW AT SML - WELCOME!, holiday rental in Pittsville

The Fun Spot 2 - BEST DOCK AND PATIO WITH A VIEW AT SML - WELCOME!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Secluded Waterfront Get Away on Smith Mountain Lake, holiday rental in Pittsville

Secluded Waterfront Get Away on Smith Mountain Lake

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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SPECIAL RATES  GORGEOUS HOME WITH AMAZING VIEWS  NO WAKE COVE  KAYAKSAKS 4 RENT, holiday rental in Pittsville

SPECIAL RATES GORGEOUS HOME WITH AMAZING VIEWS NO WAKE COVE KAYAKSAKS 4 RENT

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Affordable Waterfront Cottage near base of Smith Mountain, Great Views, holiday rental in Pittsville

Affordable Waterfront Cottage near base of Smith Mountain, Great Views

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront Vacation Retreat on Smith Mountain Lake, holiday rental in Pittsville

Waterfront Vacation Retreat on Smith Mountain Lake

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Home w/Gorgeous Mountain Views!  Sleeps 13! Perfect for families!, holiday rental in Pittsville

Waterfront Home w/Gorgeous Mountain Views! Sleeps 13! Perfect for families!

4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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EastlakeEstateSML  -  Spectacular Sunsets, HotTub, Covered Boat Dock, Game Room, holiday rental in Pittsville

EastlakeEstateSML - Spectacular Sunsets, HotTub, Covered Boat Dock, Game Room

6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Huge Waterfront Home, on Golf Course, Pools, Beaches, Tennis & More!, holiday rental in Pittsville

Huge Waterfront Home, on Golf Course, Pools, Beaches, Tennis & More!

5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Belview Bay Stay and Play--Freshly updated, holiday rental in Pittsville

Belview Bay Stay and Play--Freshly updated

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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'LAKE Pleasant'  Lake Front, Private Dock, 4 Bedrooms, Outside decks and dining., holiday rental in Pittsville

'LAKE Pleasant' Lake Front, Private Dock, 4 Bedrooms, Outside decks and dining.

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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2 Bed 2 Bath Condo, lake & mountain views. Discounted Golf, Charted Boat rides, holiday rental in Pittsville

2 Bed 2 Bath Condo, lake & mountain views. Discounted Golf, Charted Boat rides

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful New  Lakefront Home On Smith Mountain Lake., holiday rental in Pittsville

Beautiful New Lakefront Home On Smith Mountain Lake.

3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Lakefront Condo with lovely  views, holiday rental in Pittsville

Beautiful Lakefront Condo with lovely views

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Affordable Cottage in a Quiet Cove on Beautiful Smith Mountain Lake., holiday rental in Pittsville

Affordable Cottage in a Quiet Cove on Beautiful Smith Mountain Lake.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful, Quiet Lakefront Property - Smith Mountain Lake ~VA~, holiday rental in Pittsville

Beautiful, Quiet Lakefront Property - Smith Mountain Lake ~VA~

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Booking summer 2021! Kayaks*SUP*Deep PRIVATE Cove**Shuffleboard*PoolTable, holiday rental in Pittsville

Booking summer 2021! Kayaks*SUP*Deep PRIVATE Cove**Shuffleboard*PoolTable

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Boat Ramp, Pool, Fire Pit, Kayaks, Gas Grill, Flat Lot, Huge Dock & Ping Pong!, holiday rental in Pittsville

Boat Ramp, Pool, Fire Pit, Kayaks, Gas Grill, Flat Lot, Huge Dock & Ping Pong!

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Coolest House On SML!, holiday rental in Pittsville

Coolest House On SML!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Welcome Hikers, Cyclers, Writers, And Dreamers...., holiday rental in Pittsville

Welcome Hikers, Cyclers, Writers, And Dreamers....

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Lakefront Views, holiday rental in Pittsville

Beautiful Lakefront Views

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Smith Mountain Lake Waterfront Property - Olde Stoney, holiday rental in Pittsville

Beautiful Smith Mountain Lake Waterfront Property - Olde Stoney

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautifully Decorated Cabin Pristine and Peaceful!, holiday rental in Pittsville

Beautifully Decorated Cabin Pristine and Peaceful!

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Love Sunsets?   Glory in a natural and rustic setting, holiday rental in Pittsville

Love Sunsets? Glory in a natural and rustic setting

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pick Belview Bay Getaway at SML for the Gorgeous Sunset View, holiday rental in Pittsville

Pick Belview Bay Getaway at SML for the Gorgeous Sunset View

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Romantic condo with beautiful sunset views of Smith Mountain Lake, holiday rental in Pittsville

Romantic condo with beautiful sunset views of Smith Mountain Lake

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Shangri La Family town home with Internet, holiday rental in Pittsville

Shangri La Family town home with Internet

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Large Comfortable Cottage with Amazing views!, holiday rental in Pittsville

Large Comfortable Cottage with Amazing views!

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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French Tudor Mansion. 8400 sf. Nicest rental property on Smith Mountain Lake!, holiday rental in Pittsville

French Tudor Mansion. 8400 sf. Nicest rental property on Smith Mountain Lake!

7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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BOOKING 2021!  BEST VIEWS, holiday rental in Pittsville

BOOKING 2021! BEST VIEWS

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Welcome to a Hidden Gem, holiday rental in Pittsville

Welcome to a Hidden Gem

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Studio on Smith Mountain Lake - Near Golf Courses!, holiday rental in Pittsville

Studio on Smith Mountain Lake - Near Golf Courses!

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Huddleston Condo w/ Balcony on Smith Mountain Lake, holiday rental in Pittsville

Huddleston Condo w/ Balcony on Smith Mountain Lake

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Meadows at Bernard`s Landing, holiday rental in Pittsville

The Meadows at Bernard`s Landing

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to Lakefield Cove!  Sleeps 7, holiday rental in Pittsville

Welcome to Lakefield Cove! Sleeps 7

4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Resort Condo w/ Pool Access on Smith Mountain Lake, holiday rental in Pittsville

Resort Condo w/ Pool Access on Smith Mountain Lake

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW! Lakefront Living w/ Dock, Fire Pit & Sunroom!, holiday rental in Pittsville

NEW! Lakefront Living w/ Dock, Fire Pit & Sunroom!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mariners Landing Hospitality waterfront condos, holiday rental in Pittsville

Mariners Landing Hospitality waterfront condos

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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