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Chester Gap Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Chester Gap.
Modern Mountain Retreat w/ Deck + Hot Tub!, vacation rental in Chester Gap
Modern Mountain Retreat w/ Deck + Hot Tub!, vacation rental in Chester Gap
Modern Mountain Retreat w/ Deck + Hot Tub!, vacation rental in Chester Gap

Modern Mountain Retreat w/ Deck + Hot Tub!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Nest at Chester Gap, vacation rental in Chester Gap
The Nest at Chester Gap, vacation rental in Chester Gap
The Nest at Chester Gap, vacation rental in Chester Gap

The Nest at Chester Gap

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern Living in the Mountains, vacation rental in Chester Gap
Modern Living in the Mountains, vacation rental in Chester Gap
Modern Living in the Mountains, vacation rental in Chester Gap

Modern Living in the Mountains

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The following properties within 20 miles of Chester Gap match all your filters:
New! Sapphire Ridge | Escape to Shenandoah River | Hot Tub!, vacation rental in Chester Gap
New! Sapphire Ridge | Escape to Shenandoah River | Hot Tub!, vacation rental in Chester Gap
New! Sapphire Ridge | Escape to Shenandoah River | Hot Tub!, vacation rental in Chester Gap

New! Sapphire Ridge | Escape to Shenandoah River | Hot Tub!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal, vacation rental in Chester Gap
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal, vacation rental in Chester Gap
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal, vacation rental in Chester Gap

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Pond Cabin: Hot Tub & Stocked Pond, vacation rental in Chester Gap
The Pond Cabin: Hot Tub & Stocked Pond, vacation rental in Chester Gap
The Pond Cabin: Hot Tub & Stocked Pond, vacation rental in Chester Gap

The Pond Cabin: Hot Tub & Stocked Pond

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly, vacation rental in Chester Gap
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly, vacation rental in Chester Gap
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly, vacation rental in Chester Gap

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Hidden Gem on Hidden Valley Lane, vacation rental in Chester Gap
Hidden Gem on Hidden Valley Lane, vacation rental in Chester Gap
Hidden Gem on Hidden Valley Lane, vacation rental in Chester Gap

Hidden Gem on Hidden Valley Lane

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Home w/ Hot Tub Near Shenandoah Nat'l Park!, vacation rental in Chester Gap
Home w/ Hot Tub Near Shenandoah Nat'l Park!, vacation rental in Chester Gap
Home w/ Hot Tub Near Shenandoah Nat'l Park!, vacation rental in Chester Gap

Home w/ Hot Tub Near Shenandoah Nat'l Park!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Deer Haven | Blue Mountain Retreat w/ Hot Tub, vacation rental in Chester Gap
Deer Haven | Blue Mountain Retreat w/ Hot Tub, vacation rental in Chester Gap
Deer Haven | Blue Mountain Retreat w/ Hot Tub, vacation rental in Chester Gap

Deer Haven | Blue Mountain Retreat w/ Hot Tub

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beautiful historic farmhouse and stream at the foot of the Blue Ridge Mountains, vacation rental in Chester Gap
Beautiful historic farmhouse and stream at the foot of the Blue Ridge Mountains, vacation rental in Chester Gap
Beautiful historic farmhouse and stream at the foot of the Blue Ridge Mountains, vacation rental in Chester Gap

Beautiful historic farmhouse and stream at the foot of the Blue Ridge Mountains

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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� Hottub + � friendly + ️ view + Skyline Dr + Wineries, vacation rental in Chester Gap
� Hottub + � friendly + ️ view + Skyline Dr + Wineries, vacation rental in Chester Gap
� Hottub + � friendly + ️ view + Skyline Dr + Wineries, vacation rental in Chester Gap

� Hottub + � friendly + ️ view + Skyline Dr + Wineries

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Mountain cabin near national park & wineries, vacation rental in Chester Gap
Mountain cabin near national park & wineries, vacation rental in Chester Gap
Mountain cabin near national park & wineries, vacation rental in Chester Gap

Mountain cabin near national park & wineries

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cute cabin retreat near Shenandoah National Park and pet friendly!, vacation rental in Chester Gap
Cute cabin retreat near Shenandoah National Park and pet friendly!, vacation rental in Chester Gap
Cute cabin retreat near Shenandoah National Park and pet friendly!, vacation rental in Chester Gap

Cute cabin retreat near Shenandoah National Park and pet friendly!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Mountain View Vacation Home, vacation rental in Chester Gap
Beautiful Mountain View Vacation Home, vacation rental in Chester Gap
Beautiful Mountain View Vacation Home, vacation rental in Chester Gap

Beautiful Mountain View Vacation Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large and Sunny Inviting West Side Facing Room in the Valley, vacation rental in Chester Gap
Large and Sunny Inviting West Side Facing Room in the Valley, vacation rental in Chester Gap
Large and Sunny Inviting West Side Facing Room in the Valley, vacation rental in Chester Gap

Large and Sunny Inviting West Side Facing Room in the Valley

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Hazegrov in Virginia Wine Country, vacation rental in Chester Gap
Hazegrov in Virginia Wine Country, vacation rental in Chester Gap
Hazegrov in Virginia Wine Country, vacation rental in Chester Gap

Hazegrov in Virginia Wine Country

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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A nice and cozy home ! Close to almost everything!, vacation rental in Chester Gap
A nice and cozy home ! Close to almost everything!, vacation rental in Chester Gap
A nice and cozy home ! Close to almost everything!, vacation rental in Chester Gap

A nice and cozy home ! Close to almost everything!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cozy Front Royal Apt, 2 Mi to Skyline Caverns, vacation rental in Chester Gap
Cozy Front Royal Apt, 2 Mi to Skyline Caverns, vacation rental in Chester Gap
Cozy Front Royal Apt, 2 Mi to Skyline Caverns, vacation rental in Chester Gap

Cozy Front Royal Apt, 2 Mi to Skyline Caverns

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Royal Loft, Modern 1 Bedroom, Front Royal, VA, vacation rental in Chester Gap
The Royal Loft, Modern 1 Bedroom, Front Royal, VA, vacation rental in Chester Gap
The Royal Loft, Modern 1 Bedroom, Front Royal, VA, vacation rental in Chester Gap

The Royal Loft, Modern 1 Bedroom, Front Royal, VA

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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John Pope Cabin A beautifully 1865 renovated authentic log cabin, vacation rental in Chester Gap
John Pope Cabin A beautifully 1865 renovated authentic log cabin, vacation rental in Chester Gap
John Pope Cabin A beautifully 1865 renovated authentic log cabin, vacation rental in Chester Gap

John Pope Cabin A beautifully 1865 renovated authentic log cabin

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Chic Front Royal Retreat Near Shenandoah River!, vacation rental in Chester Gap
Chic Front Royal Retreat Near Shenandoah River!, vacation rental in Chester Gap
Chic Front Royal Retreat Near Shenandoah River!, vacation rental in Chester Gap

Chic Front Royal Retreat Near Shenandoah River!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming Front Royal Retreat ~ 1 Mi to River!, vacation rental in Chester Gap
Charming Front Royal Retreat ~ 1 Mi to River!, vacation rental in Chester Gap
Charming Front Royal Retreat ~ 1 Mi to River!, vacation rental in Chester Gap

Charming Front Royal Retreat ~ 1 Mi to River!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Trout's Loft 2 Bedroom, Historic Downtown Front Royal, VA, vacation rental in Chester Gap
Trout's Loft 2 Bedroom, Historic Downtown Front Royal, VA, vacation rental in Chester Gap
Trout's Loft 2 Bedroom, Historic Downtown Front Royal, VA, vacation rental in Chester Gap

Trout's Loft 2 Bedroom, Historic Downtown Front Royal, VA

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Central Front Royal Getaway on Main Street!, vacation rental in Chester Gap
Central Front Royal Getaway on Main Street!, vacation rental in Chester Gap
Central Front Royal Getaway on Main Street!, vacation rental in Chester Gap

Central Front Royal Getaway on Main Street!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Historic Schoolhouse in Linden w/ Pool -- Close to wineries, nat'l park & more!, vacation rental in Chester Gap
Historic Schoolhouse in Linden w/ Pool -- Close to wineries, nat'l park & more!, vacation rental in Chester Gap
Historic Schoolhouse in Linden w/ Pool -- Close to wineries, nat'l park & more!, vacation rental in Chester Gap

Historic Schoolhouse in Linden w/ Pool -- Close to wineries, nat'l park & more!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Warren House: 5 minutes to Shenandoah National Park!, vacation rental in Chester Gap
The Warren House: 5 minutes to Shenandoah National Park!, vacation rental in Chester Gap
The Warren House: 5 minutes to Shenandoah National Park!, vacation rental in Chester Gap

The Warren House: 5 minutes to Shenandoah National Park!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Fox Hollow - Walk to Winery! Close to Shenandoah, vacation rental in Chester Gap
Fox Hollow - Walk to Winery! Close to Shenandoah, vacation rental in Chester Gap
Fox Hollow - Walk to Winery! Close to Shenandoah, vacation rental in Chester Gap

Fox Hollow - Walk to Winery! Close to Shenandoah

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Liberty Hall Cabin - Family Retreat with a View!, vacation rental in Chester Gap
Liberty Hall Cabin - Family Retreat with a View!, vacation rental in Chester Gap
Liberty Hall Cabin - Family Retreat with a View!, vacation rental in Chester Gap

Liberty Hall Cabin - Family Retreat with a View!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Rappahannock's Vineyard Cottage!, vacation rental in Chester Gap
Rappahannock's Vineyard Cottage!, vacation rental in Chester Gap
Rappahannock's Vineyard Cottage!, vacation rental in Chester Gap

Rappahannock's Vineyard Cottage!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Unique Cliffside Home near Skyline Drive & Caverns, vacation rental in Chester Gap
Unique Cliffside Home near Skyline Drive & Caverns, vacation rental in Chester Gap
Unique Cliffside Home near Skyline Drive & Caverns, vacation rental in Chester Gap

Unique Cliffside Home near Skyline Drive & Caverns

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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New! Modern family cottage oasis with fast WiFi and pet friendly., vacation rental in Chester Gap
New! Modern family cottage oasis with fast WiFi and pet friendly., vacation rental in Chester Gap
New! Modern family cottage oasis with fast WiFi and pet friendly., vacation rental in Chester Gap

New! Modern family cottage oasis with fast WiFi and pet friendly.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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3BR 3 Level Chalet 60 Mi. W of Washington DC (Linden/Front Royal Va)-ADULTS ONLY, vacation rental in Chester Gap
3BR 3 Level Chalet 60 Mi. W of Washington DC (Linden/Front Royal Va)-ADULTS ONLY, vacation rental in Chester Gap
3BR 3 Level Chalet 60 Mi. W of Washington DC (Linden/Front Royal Va)-ADULTS ONLY, vacation rental in Chester Gap

3BR 3 Level Chalet 60 Mi. W of Washington DC (Linden/Front Royal Va)-ADULTS ONLY

Rental Home
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Front Royal Retreat ~ 1 Mi to National Park!, vacation rental in Chester Gap
Front Royal Retreat ~ 1 Mi to National Park!, vacation rental in Chester Gap
Front Royal Retreat ~ 1 Mi to National Park!, vacation rental in Chester Gap

Front Royal Retreat ~ 1 Mi to National Park!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cabin Retreat w/ Hot Tub Near Wineries and Hiking, vacation rental in Chester Gap
Cabin Retreat w/ Hot Tub Near Wineries and Hiking, vacation rental in Chester Gap
Cabin Retreat w/ Hot Tub Near Wineries and Hiking, vacation rental in Chester Gap

Cabin Retreat w/ Hot Tub Near Wineries and Hiking

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cedarbank • Cabin in Virginia Wine Country, vacation rental in Chester Gap
Cedarbank • Cabin in Virginia Wine Country, vacation rental in Chester Gap
Cedarbank • Cabin in Virginia Wine Country, vacation rental in Chester Gap

Cedarbank • Cabin in Virginia Wine Country

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Mountain Cabin Getaway | Hot Tub | Wineries & Hiking Nearby, vacation rental in Chester Gap
Mountain Cabin Getaway | Hot Tub | Wineries & Hiking Nearby, vacation rental in Chester Gap
Mountain Cabin Getaway | Hot Tub | Wineries & Hiking Nearby, vacation rental in Chester Gap

Mountain Cabin Getaway | Hot Tub | Wineries & Hiking Nearby

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private Cabin Retreat w/ Shenandoah Valley View, vacation rental in Chester Gap
Private Cabin Retreat w/ Shenandoah Valley View, vacation rental in Chester Gap
Private Cabin Retreat w/ Shenandoah Valley View, vacation rental in Chester Gap

Private Cabin Retreat w/ Shenandoah Valley View

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Pet-Friendly Home in Heart of Wine Country!, vacation rental in Chester Gap
Pet-Friendly Home in Heart of Wine Country!, vacation rental in Chester Gap
Pet-Friendly Home in Heart of Wine Country!, vacation rental in Chester Gap

Pet-Friendly Home in Heart of Wine Country!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Idle Hour at Chester Gap, vacation rental in Chester Gap
Idle Hour at Chester Gap, vacation rental in Chester Gap
Idle Hour at Chester Gap, vacation rental in Chester Gap

Idle Hour at Chester Gap

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Spacious home steps from Main St and Shenandoah NP with firepit & large backyard, vacation rental in Chester Gap
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard, vacation rental in Chester Gap
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard, vacation rental in Chester Gap

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Big Sunny Family House, vacation rental in Chester Gap
Big Sunny Family House, vacation rental in Chester Gap
Big Sunny Family House, vacation rental in Chester Gap

Big Sunny Family House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Linden Cabin w/ Hot Tub + Mountain Views!, vacation rental in Chester Gap
Linden Cabin w/ Hot Tub + Mountain Views!, vacation rental in Chester Gap
Linden Cabin w/ Hot Tub + Mountain Views!, vacation rental in Chester Gap

Linden Cabin w/ Hot Tub + Mountain Views!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Luxury Lodge Pet Friendly & Hot Tub in Shenandoah, vacation rental in Chester Gap
Luxury Lodge Pet Friendly & Hot Tub in Shenandoah, vacation rental in Chester Gap
Luxury Lodge Pet Friendly & Hot Tub in Shenandoah, vacation rental in Chester Gap

Luxury Lodge Pet Friendly & Hot Tub in Shenandoah

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Vineyard Vista, vacation rental in Chester Gap
Vineyard Vista, vacation rental in Chester Gap
Vineyard Vista, vacation rental in Chester Gap

Vineyard Vista

Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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Panoramic Blue Ridge Mountain and Rolling Farm Field Views!, vacation rental in Chester Gap
Panoramic Blue Ridge Mountain and Rolling Farm Field Views!, vacation rental in Chester Gap
Panoramic Blue Ridge Mountain and Rolling Farm Field Views!, vacation rental in Chester Gap

Panoramic Blue Ridge Mountain and Rolling Farm Field Views!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Harmony Ridge Hideaway: mountain retreat w/hot tub, vacation rental in Chester Gap
Harmony Ridge Hideaway: mountain retreat w/hot tub, vacation rental in Chester Gap
Harmony Ridge Hideaway: mountain retreat w/hot tub, vacation rental in Chester Gap

Harmony Ridge Hideaway: mountain retreat w/hot tub

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Perfect Location! Modern Mountain Home with lots of charm, vacation rental in Chester Gap
Perfect Location! Modern Mountain Home with lots of charm, vacation rental in Chester Gap
Perfect Location! Modern Mountain Home with lots of charm, vacation rental in Chester Gap

Perfect Location! Modern Mountain Home with lots of charm

Rental Home
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
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Charming modern home in the mountains, vacation rental in Chester Gap
Charming modern home in the mountains, vacation rental in Chester Gap
Charming modern home in the mountains, vacation rental in Chester Gap

Charming modern home in the mountains

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Mountain Views in Buena Vista Farm, vacation rental in Chester Gap
Mountain Views in Buena Vista Farm, vacation rental in Chester Gap
Mountain Views in Buena Vista Farm, vacation rental in Chester Gap

Mountain Views in Buena Vista Farm

Rental Home
2 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Showing results 1-50 of 50
Frequently Asked Questions about Chester Gap