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
$195 – $250/ night(excl. fees & taxes)
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

Oct 26 – 29, 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 22 – 27, 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

$2,140.58 USD total for 3 nights

Nov 8 – 11, 2026

Enjoy an idyllic off season getaway.
Enjoy a sunset drink overlooking sweeping views of the Rappahannock and listening to the waves break against the riprap.
Fall and winter days at the river can’t be beat! Look out at the water while snuggling by the fireplace.
As soon as you walk up to the cottage, you see the expansive river waiting for you on the other side. Our charming cottage and white picket fence, which we like to think has English cottage vibes.
Cozy Waterfront Getaway Fireplace/Kayaks/Fire Pit

Cozy Waterfront Getaway Fireplace/Kayaks/Fire Pit

3 bedrooms·3 baths
Locust Hill • Virginia
4.97(77 reviews)

$801.87 USD total for 3 nights

Oct 25 – 28, 2026

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 22 – 25, 2026

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

$1,490.22 USD total for 3 nights

Oct 22 – 25, 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·1½ baths
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(14 reviews)

$1,380.94 USD $1,208.21 USD total for 3 nights

Oct 22 – 25, 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 22 – 25, 2026

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)

$1,337.70 USD total for 3 nights

Oct 22 – 25, 2026

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

Oct 25 – 28, 2026