Location

Dates

Guests

Vacation rentals in Virginia

Parkside South, Cape Charles image 1

Parkside South, Cape Charles image 2

Parkside South, Cape Charles image 3

Parkside South, Cape Charles image 4

Parkside South, Cape Charles image 5

Parkside South, Cape Charles

2 bedrooms·1½ baths

Cape Charles • Virginia

4.98(46 reviews)

$1,000 – $1,001/ night(excl. fees & taxes)

Pinkberry Cottage by Bayberry Cottages

Pinkberry Cottage by Bayberry Cottages

Pinkberry Cottage by Bayberry Cottages

Pinkberry Cottage by Bayberry Cottages

Let’s flamingle on the front porch swing.

Pinkberry Cottage by Bayberry Cottages

5 bedrooms·3 baths

Cape Charles • Virginia

5(3 reviews)

$1,752.65 USD total for 3 nights

Oct 19 – 22, 2026

Stylish family getaway just steps away from the beach/town

Relax on our front porch

We offer comfortable and relaxed seating

The living area offers a Smart TV with streaming capabilities. We have games and books in the drawers of the coffee table.

The Salty Plum

4 bedrooms·2½ baths

Northampton County • Virginia

5(1 review)

$1,377.92 USD total for 3 nights

Oct 19 – 22, 2026

Front of home situated on four acres

The Refuge at Laurel

The Refuge at Laurel

The Refuge at Laurel

The Refuge at Laurel

The Refuge at Laurel

2 bedrooms·1 bath

Shipman • Virginia

4.87(126 reviews)

$495.00 USD total for 3 nights

Oct 25 – 28, 2026

Inviting Living Room with Fireplace

Inviting Entryway with Beautiful Views

Inviting Pathway to the Back Entrance

Inviting Side View of the Home

Breathtaking Massanutten Mountain Vista

Speedway Stay - 4 bedrooms in town

4 bedrooms·1 bath

Shenandoah • Virginia

4.7(27 reviews)

$630.94 USD $541.88 USD total for 3 nights

Oct 19 – 22, 2026

Welcome to the farmhouse!

Old Rag Foothills

4 bedrooms·3 baths

Sperryville • Virginia

5(113 reviews)

$1,653.79 USD total for 3 nights

Oct 25 – 28, 2026

Valley Peace: Historic Stay, New Market VA

Valley Peace: Historic Stay, New Market VA

Valley Peace: Historic Stay, New Market VA

Valley Peace: Historic Stay, New Market VA

Valley Peace: Historic Stay, New Market VA

Valley Peace: Historic Stay, New Market VA

1 bedroom·1 bath

Shenandoah County • Virginia

5(17 reviews)

$495.00 USD total for 3 nights

Oct 19 – 22, 2026

Paradise View Cabin | Private Mountain Vista + Spa image 1

Paradise View Cabin | Private Mountain Vista + Spa image 2

Paradise View Cabin | Private Mountain Vista + Spa image 3

Paradise View Cabin | Private Mountain Vista + Spa image 4

Paradise View Cabin | Private Mountain Vista + Spa image 5

Paradise View Cabin | Private Mountain Vista + Spa

2 bedrooms·2 baths

Luray • Virginia

5(110 reviews)

$1,369.60 USD total for 3 nights

Oct 19 – 22, 2026

Winter view of the Blue Ridge Mountains and the Shenandoah River.

Welcome to Bluebird Hill

You know you are in the right place!

Bluebird Hill Cabin ~ Hiking ~ Wineries

View from the kitchen of LR and dining area. Relax by the fire while enjoying TV and the view.

Bluebird Hill Cabin ~ Hiking ~ Wineries

3 bedrooms·3½ baths

Front Royal • Virginia

5(1 review)

$1,275.06 USD total for 3 nights

Dec 5 – 8, 2026

Waterfront Oasis W/ Pickleball Court & Hot tub

Waterfront Oasis W/ Pickleball Court & Hot tub

Waterfront Oasis W/ Pickleball Court & Hot tub

Waterfront Oasis W/ Pickleball Court & Hot tub

Waterfront Oasis W/ Pickleball Court & Hot tub

Waterfront Oasis W/ Pickleball Court & Hot tub

9 bedrooms·7 baths

Richmond • Virginia

5(14 reviews)

$8,453.52 USD total for 5 nights

Oct 19 – 24, 2026

C'ville Woods

2 bedrooms·2½ baths

Charlottesville • Virginia

$2,811.51 USD total for 30 nights

Oct 19 – Nov 18, 2026

Cruise Ctrl: Family Friendly House, Fenced in Yard image 1

Cruise Ctrl: Family Friendly House, Fenced in Yard image 5

Cruise Ctrl: Family Friendly House, Fenced in Yard image 6

Cruise Ctrl: Family Friendly House, Fenced in Yard image 7

Cruise Ctrl: Family Friendly House, Fenced in Yard image 13

Cruise Ctrl: Family Friendly House, Fenced in Yard

3 bedrooms·2 baths

Cape Charles • Virginia

4.9(10 reviews)

$1,337.70 USD total for 3 nights

Oct 19 – 22, 2026

8BR | SwimSpa | Games | OMG Views | Outdoor Living image 1

8BR | SwimSpa | Games | OMG Views | Outdoor Living image 2

8BR | SwimSpa | Games | OMG Views | Outdoor Living image 3

8BR | SwimSpa | Games | OMG Views | Outdoor Living image 4

8BR | SwimSpa | Games | OMG Views | Outdoor Living image 5

Obsidian Escape - Managed by Gr8Escapes

8 bedrooms·6 baths

Massanutten • Virginia

$3,489.55 USD total for 3 nights

Oct 19 – 22, 2026

8BR | SwimSpa | Theater | Speakeasy | OMG Views image 1

8BR | SwimSpa | Theater | Speakeasy | OMG Views image 2

8BR | SwimSpa | Theater | Speakeasy | OMG Views image 3

8BR | SwimSpa | Theater | Speakeasy | OMG Views image 4

8BR | SwimSpa | Theater | Speakeasy | OMG Views image 5

Sunstone Escape - Managed by Gr8Escapes

8 bedrooms·7 baths

Massanutten • Virginia

$3,489.55 USD total for 3 nights

Oct 20 – 23, 2026

Charming 2-story with covered porch, wooded privacy, and ample parking

Litorum - a place to land, breathe, and reset.

Covered porch with forest views and stacked firewood—peaceful retreat

Cozy 2-story with wraparound porch, large yard & ample parking

Charming wooded retreat with front porch and ample parking

Litorum - a place to land, breathe, and reset.

4 bedrooms·3½ baths

Front Royal • Virginia

4.5(6 reviews)

$1,063.08 USD total for 3 nights

Oct 19 – 22, 2026

Smith Mountain Lake Retreat image 1

Smith Mountain Lake Retreat image 2

Smith Mountain Lake Retreat image 3

Smith Mountain Lake Retreat image 4

Smith Mountain Lake Retreat image 5

Smith Mountain Lake Retreat

3 bedrooms·2 baths

Moneta • Virginia

4.96(26 reviews)

$2,456.30 USD total for 5 nights

Oct 25 – 30, 2026

Modern Mainstay near VCU and Convention Center

Modern Mainstay near VCU and Convention Center

Modern Mainstay near VCU and Convention Center

Modern Mainstay near VCU and Convention Center

Modern Mainstay near VCU and Convention Center

Modern Mainstay near VCU and Convention Center

3 bedrooms·2½ baths

Richmond • Virginia

5(6 reviews)

$784.00 USD total for 3 nights

Oct 19 – 22, 2026

Valley Joy: Rustic French Retreat, New Market VA

Valley Joy: Rustic French Retreat, New Market VA

Valley Joy: Rustic French Retreat, New Market VA

As you step inside, you’ll be greeted by a warm and inviting living room, featuring a plush sofa that beckons you to relax and unwind. Whether you’re curling up with a good book or enjoying a movie night on the flat-screen TV.

Valley Joy: Rustic French Retreat, New Market VA

Valley Joy: Rustic French Retreat, New Market VA

1 bedroom·1 bath

Shenandoah County • Virginia

5(11 reviews)

$410.00 USD total for 3 nights

Oct 19 – 22, 2026

View from upstairs windows.

Relax by the fire with stunning creek views. Perfect spot to unwind, sip a drink, and enjoy peaceful waterfront evenings at Crazy Whays Retreat.

Charming waterfront retreat with private dock access and plenty of parking. A peaceful, tucked-away escape perfect for relaxing and reconnecting with nature.

Waterfront House with Private Dock and Fishing

Perfect spot, at the end of the pier, to sit with a cup of coffee and watch the sun rise and set

Waterfront House with Private Dock and Fishing

3 bedrooms·2 baths

Reedville • Virginia

$956.12 USD total for 3 nights

Oct 24 – 27, 2026

Waterfront retreat with pool, hot tub, private playground, huge yard & scenic views. Perfect for family getaways & special moments—relax, play, and explore the best of the Bay from this unforgettable coastal escape!

Enjoy your own private, heated, pool with stunning waterfront scenery! Lounge in style, sip under the red umbrella, and unwind as the sun sets over the bay. The perfect spot for relaxation and connection.

Front-row seats to the bay!
Start your morning or end your day in these colorful Adirondack chairs with uninterrupted views of the water and private pier—pure peace and coastal charm await.

Unwind in the indoor hot tub with panoramic water views and cozy string lights overhead. Whether it’s morning coffee or a sunset soak, this spot is pure bliss—rain or shine!

Fire up the grills and gather around the bar or relax beneath twinkling lights with waterfront views. This cozy, shaded space is perfect for sunset dinners, family cookouts, and laid-back evenings at The Fleeton House.

Bayfront Oasis | Heated Pool, HotTub & Playground

6 bedrooms·3½ baths

Reedville • Virginia

$2,783.14 USD total for 3 nights

Oct 20 – 23, 2026

NEW (July 2023) outdoor TV

Front view of house

New (July 2023) front porch!

Rockfish Valley Retreat- Wintergreen image 4

Rockfish Valley Retreat- Wintergreen

3 bedrooms·2 baths

Nellysford • Virginia

4.96(23 reviews)

$3,000.00 USD total for 3 nights

Oct 19 – 22, 2026

The Baldwin Flat - furnished for long-term stays

Sectional couch

The Baldwin Flat - furnished for long-term stays

The Baldwin Flat - furnished for long-term stays

The Baldwin Flat - furnished for long-term stays

The Baldwin Flat - furnished for long-term stays

2 bedrooms·1 bath

Warrenton • Virginia

4.8(5 reviews)

$7,018.72 USD total for 30 nights

Nov 30 – Dec 30, 2026

Exterior detail

Private kitchen

Private kitchen

Slow Mocean: Family Friendly 3 Bedroom Home

3 bedrooms·2 baths

Cape Charles • Virginia

5(8 reviews)

$1,337.70 USD total for 3 nights

Oct 19 – 22, 2026

Welcome to the Lyellton House!

Upstairs living room with kitchenette.

Upstairs living room with smart tv and pull out couch.

Spacious den with smart tv, door that leads to back deck and couch that pulls out into a queen bed if needed.
*Please note we only have 2 sofas not 3 at this time. There are 2 chairs in the corner

First floor primary bedroom with Queen bed and ensuite bathroom.

The Lyellton House: Water View, Steps from Beach

6 bedrooms·4 baths

Colonial Beach • Virginia

$2,229.34 USD total for 3 nights

Oct 30 – Nov 2, 2026