Massanutten Home 10 guests, 5 bds, Ski-In/Ski-Out image 1
Massanutten Home 10 guests, 5 bds, Ski-In/Ski-Out image 2
Massanutten Home 10 guests, 5 bds, Ski-In/Ski-Out image 3
Massanutten Home 10 guests, 5 bds, Ski-In/Ski-Out image 4
Massanutten Home 10 guests, 5 bds, Ski-In/Ski-Out image 5

Retreat at Massanutten Near Skiing & Water Park

3 bedrooms·2½ baths
McGaheysville • Virginia
5(1 review)

$1,000.00 USD total for 3 nights

Oct 25 – 28, 2026

Private cedar barrel sauna—your onsite spa retreat with bench seating
Bright modern living space with slat wall art and patio access
Covered deck with fire pit, lounge seating & sweeping mountain views
Private deck with sweeping valley views—perfect for sunset wine.
Modern game room: pool, foosball, and retro arcade—fun for everyone

Skycrest Cabin - NEW!

4 bedrooms·4 baths
Shenandoah Farms • Virginia
4.67(3 reviews)

$1,572.44 USD total for 3 nights

Oct 19 – 22, 2026

The Bagley House: built in 1911
The Bagley House: built in 1911
The Bagley House: built in 1911
The Bagley House: built in 1911
The Bagley House: built in 1911

The Bagley House: built in 1911

7 bedrooms·3½ baths
Blackstone • Virginia

$1,608.64 USD total for 3 nights

Oct 25 – 28, 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)

$711.20 USD total for 3 nights

Oct 25 – 28, 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

$825.80 USD $727.69 USD total for 3 nights

Oct 24 – 27, 2026

Exterior
Outdoor dining
Aerial view
Living area
Living area

Lake Anna Waterfront Family & Pet Friendly Retreat! With 5+ BRs 4 BAs.

5 bedrooms·4 baths
Spotsylvania Courthouse • Virginia

$4,773.00 USD $3,864.40 USD total for 7 nights

May 1 – 8, 2027

*If wholeness, unity, and balance are what you are looking for, this is the place for you* 1 1/2 hours from D.C. 50 minutes from Harrisonburg and Massanutten.
Magical Yurt Stay-30 min from SNP!-Mountain Views- image 2
Magical Yurt Stay-30 min from SNP!-Mountain Views- image 3
Magical Yurt Stay-30 min from SNP!-Mountain Views- image 4
Magical Yurt Stay-30 min from SNP!-Mountain Views- image 5

Sky Meadow Yurt

2 bedrooms·1 bath
Luray • Virginia
5(75 reviews)

$1,175.00 USD total for 3 nights

Oct 19 – 22, 2026

Gr8 Grand Escape | 16 BR | Sleeps 40 image 1
Gr8 Grand Escape | 16 BR | Sleeps 40 image 2
Gr8 Grand Escape | 16 BR | Sleeps 40 image 3
Gr8 Grand Escape | 16 BR | Sleeps 40 image 4
Gr8 Grand Escape | 16 BR | Sleeps 40 image 5

Gr8 Grand Escape - Managed by Gr8Escapes

16 bedrooms·13 baths
Massanutten • Virginia

$8,524.55 USD total for 3 nights

Oct 20 – 23, 2026

Lake Gaston Waterfront Anchors Away
Lake Gaston Waterfront Anchors Away
Lake Gaston Waterfront Anchors Away
Lake Gaston Waterfront Anchors Away
Lake Gaston Waterfront Anchors Away

Lake Gaston Waterfront Anchors Away

3 bedrooms·2½ baths
Bracey • Virginia

$1,349.70 USD total for 3 nights

Oct 19 – 22, 2026

Family-sized Lakehouse | Hot Tub, Sauna, Game room
Family-sized Lakehouse | Hot Tub, Sauna, Game room
Family-sized Lakehouse | Hot Tub, Sauna, Game room
Family-sized Lakehouse | Hot Tub, Sauna, Game room
Family-sized Lakehouse | Hot Tub, Sauna, Game room

Family-sized Lakehouse | Hot Tub, Sauna, Game room

5 bedrooms·3½ baths
Louisa • Virginia

$1,791.05 USD total for 3 nights

Oct 19 – 22, 2026

Fort Valley Cottage at Persimmon Hill Entire House
Fort Valley Cottage at Persimmon Hill Entire House
Fort Valley Cottage at Persimmon Hill Entire House
Fort Valley Cottage at Persimmon Hill Entire House
Fort Valley Cottage at Persimmon Hill Entire House

Fort Valley Cottage at Persimmon Hill Entire House

2 bedrooms·1 bath
Fort Valley • Virginia
4.88(96 reviews)
$180/ night(excl. fees & taxes)
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

$530.25 USD total for 3 nights

Oct 19 – 22, 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

Rivers Edge Retreat
Rivers Edge Retreat
Rivers Edge Retreat
Rivers Edge Retreat
Rivers Edge Retreat

Rivers Edge Retreat

3 bedrooms·3 baths
Warren County • Virginia
5(42 reviews)

$711.03 USD total for 3 nights

Oct 25 – 28, 2026

Relax by the fire or dine among the treetops with seasonal Blue Ridge mountain views.
Architect-designed lines, elevated decks, and a glowing welcome — Chateau Greenstone stands apart before you even step inside
Sophisticated yet relaxed - where the forest meets the firelight, with a distant view and room to gather or gaze
Covered hot tub and cedar sauna for year-round relaxation with filtered mountain views. Cozy, dry, and peaceful - this lounge is perfect place to unwind, even on rainy days
The main level opens wide for shared meals, fireside lounging, and treetop & distant views all in one easy flow.

Chateau Greenstone

6 bedrooms·4 baths
Wintergreen Resort • Virginia
5(23 reviews)

$1,958.43 USD total for 3 nights

Oct 19 – 22, 2026

Soak in our 7-person, 65-jet hot tub while taking in enchanting views and enjoying a 75” TV right in front of you. Watch your favorite game or Netflix series as you unwind. This is relaxation at its finest, where luxury and nature meet seamlessly!
Come prepared to enjoy the weather around the fire pit with our S’more station.
Covered Patio with 75' TV, Hot Tub and Patio Seating
75 inch TV + Hot Tub + Outdoor Seating = Shenandoah Soothe Escapes
Thoughtfully designed cozy living room for ultra comfort. Enjoy the board games during the day with ample sunshine. When it gets dark, turn on the electric fireplace, play a movie, tuck yourself inside a throw & enjoy your popcorn

Views, Hot Tub, Porch Cinema+Smores, Secluded

3 bedrooms·1½ baths
Luray • Virginia
$104 – $920/ night(excl. fees & taxes)
outdoor pool
Hot tub
Living Room
Game Room
Crows Nest

Family, Pet Friendly home, walk to beach, hot tub

7 bedrooms·4 baths
Virginia Beach • Virginia
5(22 reviews)

$3,300.00 USD total for 3 nights

Oct 19 – 22, 2026

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

$1,690.00 USD total for 3 nights

Feb 1 – 4, 2027

Make yourself at home and enjoy a fire in this super comfortable living space.
We welcome your dog family member at Bluebird Mountain Home
Enjoy the fully stocked coffee bar with Keurig or drip coffee.
Conveniently located in the Shomokin Springs neighborhood of Wintergreen with nearby pool and multiple trail heads and overlooks
Relax with a game of pool or play some guitar or ukulele.

Bluebird Mountain Home

4 bedrooms·3½ baths
Wintergreen Resort • Virginia

$1,418.00 USD total for 3 nights

Apr 1 – 4, 2027

Private suite Near Dulles-Full Kitchen & Patio
Private suite Near Dulles-Full Kitchen & Patio
Private suite Near Dulles-Full Kitchen & Patio
Private suite Near Dulles-Full Kitchen & Patio
Private suite Near Dulles-Full Kitchen & Patio

Private suite Near Dulles-Full Kitchen & Patio

1 bedroom·1 bath
Sterling • Virginia
5(6 reviews)

$377.00 USD $339.30 USD total for 3 nights

Mar 12 – 15, 2027

Morning coffee, coastal breeze, and front-row seats to beach life 🌊☀️ Relax and unwind from your private balcony.
Light, bright, and beachy 🌊 Vaulted ceilings, coastal décor, and plenty of space to relax after a day by the ocean.
4BR Waterfront Penthouse | Pool & Views
Bright and airy open-plan living and dining area with coastal decor – perfect for family meals and relaxing while enjoying ocean views through the large windows.
Wake up to breathtaking beach views in this cozy coastal king bedroom 🌅 Sliding doors open to your private balcony with Adirondack chairs perfect for morning coffee ☕️🐚

4BR Waterfront Penthouse | Pool & Views

4 bedrooms·3 baths
Virginia Beach • Virginia

$1,708.79 USD total for 3 nights

Oct 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

$578.28 USD total for 3 nights

Oct 19 – 22, 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

$723.56 USD total for 3 nights

Oct 19 – 22, 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

$2,181.78 USD total for 3 nights

Nov 8 – 11, 2026