Cozy comfortable living room with original hardwood floors
Sitting room open to kitchen – great for coffee, wine & conversation
Spacious Second floor Queen bedroom with comfy mattress & vanity/desk.
Firepit in the backyard perfect for making smores & memories!
Dedicated dining room with plenty of seating for 8. Can also be a great space for board and/or card games! (High chair in the laundry room for the little ones if you need it too)

Bay Dreamin' - Mathews VA

4 bedrooms·2 baths
Mathews • Virginia

$765.58 USD $675.89 USD total for 3 nights

Sep 20 – 23, 2026

The Retreat at Lilly's Neck
The Retreat at Lilly's Neck
The Retreat at Lilly's Neck
The Retreat at Lilly's Neck
The Retreat at Lilly's Neck

The Retreat at Lilly's Neck

4 bedrooms·1 bath
Moon • Virginia
4.91(23 reviews)

$510.00 USD total for 3 nights

Sep 19 – 22, 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

Sep 16 – 21, 2026

Waterfront Sunsets With Pickleball Court & Hot tub
Waterfront Sunsets With Pickleball Court & Hot tub
Waterfront Sunsets With Pickleball Court & Hot tub
Waterfront Sunsets With Pickleball Court & Hot tub
Waterfront Sunsets With Pickleball Court & Hot tub

Waterfront Sunsets With Pickleball Court & Hot tub

9 bedrooms·7 baths
Richmond • Virginia

$2,224.01 USD total for 3 nights

Sep 21 – 24, 2026

Pinkberry Cottage by Bayberry Cottages
Pinkberry Cottage by Bayberry Cottages
Pinkberry Cottage by Bayberry Cottages
Let’s flamingle on the front porch swing.
Our foyer. Drop off your things at the front door and walk into your vacation.

Pinkberry Cottage by Bayberry Cottages

5 bedrooms·3 baths
Cape Charles • Virginia
5(3 reviews)

$1,921.10 USD total for 3 nights

Sep 20 – 23, 2026

The Salty Plum
Relax on our front porch
Stylish family getaway just steps away from the beach/town
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

$1,714.82 USD total for 3 nights

Sep 16 – 19, 2026

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·1 bath
Cape Charles • Virginia
4.98(46 reviews)
$1,000 – $1,001/ night(excl. fees & taxes)
'25 Reno! 1 block to Shops/Park, 1st floor bedroom
'25 Reno! 1 block to Shops/Park, 1st floor bedroom
'25 Reno! 1 block to Shops/Park, 1st floor bedroom
'25 Reno! 1 block to Shops/Park, 1st floor bedroom
'25 Reno! 1 block to Shops/Park, 1st floor bedroom

'25 Reno! 1 block to Shops/Park, 1st floor bedroom

4 bedrooms·3 baths
Cape Charles • Virginia
5(13 reviews)

$1,680.78 USD $1,448.10 USD total for 3 nights

Sep 19 – 22, 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)
$300 – $350/ night(excl. fees & taxes)
Exterior detail
Living area
Living area
Private kitchen
Private kitchen

Slow Mocean: Family Friendly 3 Bedroom Home

3 bedrooms·2 baths
Cape Charles • Virginia
5(8 reviews)
$300 – $350/ night(excl. fees & taxes)
Spacious living room
Welcome!
Primary bedroom, King Suite
Outdoor propane grill and firepit.
Large kitchen

Waterfront home w/ strong Wi-Fi near Silver Beach.

4 bedrooms·2 baths
Exmore • Virginia
4.86(7 reviews)

$1,210.00 USD total for 3 nights

Sep 20 – 23, 2026

Vacation Village at Williamsburg
Vacation Village at Williamsburg
Vacation Village at Williamsburg
Vacation Village at Williamsburg
Vacation Village at Williamsburg

Vacation Village at Williamsburg

2 bedrooms·1 bath
Williamsburg • Virginia

$11,199.93 USD total for 7 nights

Sep 16 – 23, 2026