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 7 – 14, 2026

Greensprings, a Hilton Vacation Club
Greensprings, a Hilton Vacation Club
Greensprings, a Hilton Vacation Club
Greensprings, a Hilton Vacation Club
Greensprings, a Hilton Vacation Club

Greensprings, a Hilton Vacation Club

2 bedrooms·1 bath
Williamsburg • Virginia

$3,493.00 USD total for 7 nights

Sep 7 – 14, 2026

Private Cottage! On Horse Rescue in Williamsburg!
Private Cottage! On Horse Rescue in Williamsburg!
Our barn!
Private Cottage! On Horse Rescue in Williamsburg!
Private Cottage! On Horse Rescue in Williamsburg!

Private Cottage! On Horse Rescue in Williamsburg!

2 bedrooms·2 baths
Williamsburg • Virginia
4.77(35 reviews)

$726.88 USD total for 3 nights

Sep 12 – 15, 2026

The Tiny Home @ The Pines Horse Farm
The Tiny Home @ The Pines Horse Farm
The Tiny Home @ The Pines Horse Farm
The Tiny Home @ The Pines Horse Farm
The Tiny Home @ The Pines Horse Farm

The Tiny Home @ The Pines Horse Farm

1 bedroom·1 bath
Williamsburg • Virginia

$467.25 USD total for 3 nights

Sep 30 – Oct 3, 2026

Free cancellation
Colonial Timber Cottage, in the woods
Owner crafted Timber
Foyer
Foyer, mudroom, dropzone
Foyer, mudroom, drop zone

Colonial Timber Cottage Near Colonial Williamsburg

2 bedrooms·1½ baths
Lanexa • Virginia
$425/ night(excl. fees & taxes)
The Tiny Red Barn on The Reservoir-A Private Oasis
The Tiny Red Barn on The Reservoir-A Private Oasis
The Tiny Red Barn on The Reservoir-A Private Oasis
The Tiny Red Barn on The Reservoir-A Private Oasis
The Tiny Red Barn on The Reservoir-A Private Oasis

The Tiny Red Barn on The Reservoir-A Private Oasis

2 bedrooms·1 bath
Lanexa • Virginia
4.97(198 reviews)

$1,212.49 USD total for 3 nights

Sep 7 – 10, 2026

~The BeeHive! | New 4 Bedroom Listing Next to CNU!
~The BeeHive! | New 4 Bedroom Listing Next to CNU!
~The BeeHive! | New 4 Bedroom Listing Next to CNU!
~The BeeHive! | New 4 Bedroom Listing Next to CNU!
~The BeeHive! | New 4 Bedroom Listing Next to CNU!

~The BeeHive! | New 4 Bedroom Listing Next to CNU!

4 bedrooms·2 baths
Newport News • Virginia

$5,080.66 USD total for 30 nights

Nov 7 – Dec 7, 2026

Free cancellation
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 7 – 12, 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

$2,195.17 USD total for 3 nights

Sep 21 – 24, 2026

Cap2Cap cottage II Va Cap Trail
Cap2Cap cottage II Va Cap Trail
Spacious yard. The home sits on a six acre parcel
Spacious front yard on the 6 acre parcel
Cap2Cap cottage II Va Cap Trail

Cap2Cap cottage II Va Cap Trail

2 bedrooms·1 bath
Charles City • Virginia
5(1 review)

$600.00 USD total for 3 nights

Sep 7 – 10, 2026

Cozy Luxe Stay:Patio, Pool Table image 1
Cozy Luxe Stay:Patio, Pool Table image 2
Cozy Luxe Stay:Patio, Pool Table image 3
Cozy Luxe Stay:Patio, Pool Table image 4
Cozy Luxe Stay:Patio, Pool Table image 5

Cozy Luxe Stay:Patio, Pool Table

6 bedrooms·2 baths
Newport News • Virginia

$1,750.00 USD total for 3 nights

Sep 7 – 10, 2026

Main Entrance
Vaiden Inn - Rent the inn, 4 beds, kitchenette
Vaiden Inn - Rent the inn, 4 beds, kitchenette
Vaiden Inn - Rent the inn, 4 beds, kitchenette
Vaiden Inn - Rent the inn, 4 beds, kitchenette

Vaiden Inn - Rent the inn, 4 beds, kitchenette

4 bedrooms·3 baths
New Kent • Virginia
5(28 reviews)

$1,163.16 USD total for 3 nights

Sep 7 – 10, 2026

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 $643.87 USD total for 3 nights

Sep 7 – 10, 2026

❤️Ice Ice Baby❤️Downtown Newport News!
❤️Ice Ice Baby❤️Downtown Newport News!
❤️Ice Ice Baby❤️Downtown Newport News!
❤️Ice Ice Baby❤️Downtown Newport News!
❤️Ice Ice Baby❤️Downtown Newport News!

❤️Ice Ice Baby❤️Downtown Newport News!

1 bedroom·1 bath
Newport News • Virginia

$523.30 USD total for 3 nights

Sep 7 – 10, 2026

❤️The Speakeasy❤️Downtown Newport News!
❤️The Speakeasy❤️Downtown Newport News!
❤️The Speakeasy❤️Downtown Newport News!
❤️The Speakeasy❤️Downtown Newport News!
❤️The Speakeasy❤️Downtown Newport News!

❤️The Speakeasy❤️Downtown Newport News!

1 bedroom·1 bath
Newport News • Virginia

$581.77 USD total for 3 nights

Sep 19 – 22, 2026

❤️The Safe House❤️Downtown Newport News!
❤️The Safe House❤️Downtown Newport News!
❤️The Safe House❤️Downtown Newport News!
❤️The Safe House❤️Downtown Newport News!
❤️The Safe House❤️Downtown Newport News!

❤️The Safe House❤️Downtown Newport News!

1 bedroom·1 bath
Newport News • Virginia

$597.02 USD total for 3 nights

Oct 1 – 4, 2026

Free cancellation
❤️Breakfast @ Tiffany's❤️Downtown Newport News!
❤️Breakfast @ Tiffany's❤️Downtown Newport News!
❤️Breakfast @ Tiffany's❤️Downtown Newport News!
❤️Breakfast @ Tiffany's❤️Downtown Newport News!
❤️Breakfast @ Tiffany's❤️Downtown Newport News!

❤️Breakfast @ Tiffany's❤️Downtown Newport News!

1 bedroom·1 bath
Newport News • Virginia

$605.91 USD total for 3 nights

Sep 22 – 25, 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 8 – 11, 2026

Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!
Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!
Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!
Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!
Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!

Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!

3 bedrooms·1 bath
Hampton • Virginia

$670.42 USD total for 3 nights

Sep 7 – 10, 2026

Sunsets on the bay from the massive deck are why this property is called "Bay Bliss". Nothing more really needs to be said.
The front of this charming home with a fun front porch full of character. As you can see it is right on the water. There is also a foot washing station before you walk up the steps so you don't have sand in your house the entire stay.
Views of the bay while cooking dinner... it doesn't get much better than that. The open concept of this house has the kitchen flowing right into the living room so those cooking don't have to miss out on the views or the fun!
2022 spa hot tub to take your relaxation to the next level while staring out at the water.
Yes that is the stunning, panaromic view from the porch. It doesn't really get any better while cozied up around the fire.

Exclusive Beachfront Home w/ 180° Views & Hot Tub

3 bedrooms·2 baths
Hampton • Virginia
5(13 reviews)

$1,568.82 USD total for 3 nights

Oct 4 – 7, 2026