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Holiday Homes in Winston Salem

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5 km
229 rentals in Winston Salem.
The Red Door Cabin, holiday rental in Winston Salem
The Red Door Cabin, holiday rental in Winston Salem
The Red Door Cabin, holiday rental in Winston Salem

The Red Door Cabin

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Updated Hidden Gem Close to Winston/Kernersville, holiday rental in Winston Salem
Updated Hidden Gem Close to Winston/Kernersville, holiday rental in Winston Salem
Updated Hidden Gem Close to Winston/Kernersville, holiday rental in Winston Salem

Updated Hidden Gem Close to Winston/Kernersville

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunny remodeled historic home! Steps away from Old Salem, shops, dining & coffee, holiday rental in Winston Salem
Sunny remodeled historic home! Steps away from Old Salem, shops, dining & coffee, holiday rental in Winston Salem
Sunny remodeled historic home! Steps away from Old Salem, shops, dining & coffee, holiday rental in Winston Salem

Sunny remodeled historic home! Steps away from Old Salem, shops, dining & coffee

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy guest suite in Winston Salem, holiday rental in Winston Salem
Cozy guest suite in Winston Salem, holiday rental in Winston Salem
Cozy guest suite in Winston Salem, holiday rental in Winston Salem

Cozy guest suite in Winston Salem

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Private & sweet patio level apartment in downtown Winston-Salem, holiday rental in Winston Salem
Private & sweet patio level apartment in downtown Winston-Salem, holiday rental in Winston Salem
Private & sweet patio level apartment in downtown Winston-Salem, holiday rental in Winston Salem

Private & sweet patio level apartment in downtown Winston-Salem

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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NEW, Clean, Modern! 4 bed Cozy Home Close To DWNTN, holiday rental in Winston Salem
NEW, Clean, Modern! 4 bed Cozy Home Close To DWNTN, holiday rental in Winston Salem
NEW, Clean, Modern! 4 bed Cozy Home Close To DWNTN, holiday rental in Winston Salem

NEW, Clean, Modern! 4 bed Cozy Home Close To DWNTN

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Perfection in Winston-Salem Quiet Neighborhood, holiday rental in Winston Salem
Renovated Perfection in Winston-Salem Quiet Neighborhood, holiday rental in Winston Salem
Renovated Perfection in Winston-Salem Quiet Neighborhood, holiday rental in Winston Salem

Renovated Perfection in Winston-Salem Quiet Neighborhood

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Elegant Pet Friendly Ranch Home close to everything!, holiday rental in Winston Salem
Elegant Pet Friendly Ranch Home close to everything!, holiday rental in Winston Salem
Elegant Pet Friendly Ranch Home close to everything!, holiday rental in Winston Salem

Elegant Pet Friendly Ranch Home close to everything!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Downtown Winston-Salem Condo w/ Private Library!, holiday rental in Winston Salem
Downtown Winston-Salem Condo w/ Private Library!, holiday rental in Winston Salem
Downtown Winston-Salem Condo w/ Private Library!, holiday rental in Winston Salem

Downtown Winston-Salem Condo w/ Private Library!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Winston-Salem's Man Cave, holiday rental in Winston Salem
Winston-Salem's Man Cave, holiday rental in Winston Salem
Winston-Salem's Man Cave, holiday rental in Winston Salem

Winston-Salem's Man Cave

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy! ~5 Min Walk to Hospital, holiday rental in Winston Salem
Cozy! ~5 Min Walk to Hospital, holiday rental in Winston Salem
Cozy! ~5 Min Walk to Hospital, holiday rental in Winston Salem

Cozy! ~5 Min Walk to Hospital

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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3 Bedroom House - 1 mile from Mall and Hospital, holiday rental in Winston Salem
3 Bedroom House - 1 mile from Mall and Hospital, holiday rental in Winston Salem
3 Bedroom House - 1 mile from Mall and Hospital, holiday rental in Winston Salem

3 Bedroom House - 1 mile from Mall and Hospital

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Blue Door Cabin, holiday rental in Winston Salem
The Blue Door Cabin, holiday rental in Winston Salem
The Blue Door Cabin, holiday rental in Winston Salem

The Blue Door Cabin

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Classic Bungalow steps from Wake Forest University!, holiday rental in Winston Salem
Classic Bungalow steps from Wake Forest University!, holiday rental in Winston Salem
Classic Bungalow steps from Wake Forest University!, holiday rental in Winston Salem

Classic Bungalow steps from Wake Forest University!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Luxury 3BR Townhome - Sleep 6, holiday rental in Winston Salem
Luxury 3BR Townhome - Sleep 6, holiday rental in Winston Salem
Luxury 3BR Townhome - Sleep 6, holiday rental in Winston Salem

Luxury 3BR Townhome - Sleep 6

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Great 4 Long Stays! 4 Miles From Hosp & Shopping!, holiday rental in Winston Salem
Great 4 Long Stays! 4 Miles From Hosp & Shopping!, holiday rental in Winston Salem
Great 4 Long Stays! 4 Miles From Hosp & Shopping!, holiday rental in Winston Salem

Great 4 Long Stays! 4 Miles From Hosp & Shopping!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy Townhome in a Great Location, holiday rental in Winston Salem
Cozy Townhome in a Great Location, holiday rental in Winston Salem
Cozy Townhome in a Great Location, holiday rental in Winston Salem

Cozy Townhome in a Great Location

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Walking Distance To The Mall, Park, Food, Hospital, holiday rental in Winston Salem
Walking Distance To The Mall, Park, Food, Hospital, holiday rental in Winston Salem
Walking Distance To The Mall, Park, Food, Hospital, holiday rental in Winston Salem

Walking Distance To The Mall, Park, Food, Hospital

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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West End Jewel on Sunset, holiday rental in Winston Salem
West End Jewel on Sunset, holiday rental in Winston Salem
West End Jewel on Sunset, holiday rental in Winston Salem

West End Jewel on Sunset

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Vintage Modern Synthesis in the Heart of Winston-Salem, holiday rental in Winston Salem
Vintage Modern Synthesis in the Heart of Winston-Salem, holiday rental in Winston Salem
Vintage Modern Synthesis in the Heart of Winston-Salem, holiday rental in Winston Salem

Vintage Modern Synthesis in the Heart of Winston-Salem

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Big Stone Cottage Dwntwn WS! Sleeps 16, Self Check!, holiday rental in Winston Salem
Big Stone Cottage Dwntwn WS! Sleeps 16, Self Check!, holiday rental in Winston Salem
Big Stone Cottage Dwntwn WS! Sleeps 16, Self Check!, holiday rental in Winston Salem

Big Stone Cottage Dwntwn WS! Sleeps 16, Self Check!

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
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Sunlight facing entire Townhome with 2 BR & 2.5 Bath, holiday rental in Winston Salem
Sunlight facing entire Townhome with 2 BR & 2.5 Bath, holiday rental in Winston Salem
Sunlight facing entire Townhome with 2 BR & 2.5 Bath, holiday rental in Winston Salem

Sunlight facing entire Townhome with 2 BR & 2.5 Bath

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Farmhouse on the Meadow, holiday rental in Winston Salem
Farmhouse on the Meadow, holiday rental in Winston Salem
Farmhouse on the Meadow, holiday rental in Winston Salem

Farmhouse on the Meadow

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Classy Catch in Winston, holiday rental in Winston Salem
Classy Catch in Winston, holiday rental in Winston Salem
Classy Catch in Winston, holiday rental in Winston Salem

Classy Catch in Winston

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Vista Studio-Close to Downtown Wake Forest Baptist Hospital, holiday rental in Winston Salem
The Vista Studio-Close to Downtown Wake Forest Baptist Hospital, holiday rental in Winston Salem
The Vista Studio-Close to Downtown Wake Forest Baptist Hospital, holiday rental in Winston Salem

The Vista Studio-Close to Downtown Wake Forest Baptist Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Charming Ardmore Home minutes from hospitals/I-40, holiday rental in Winston Salem
Charming Ardmore Home minutes from hospitals/I-40, holiday rental in Winston Salem
Charming Ardmore Home minutes from hospitals/I-40, holiday rental in Winston Salem

Charming Ardmore Home minutes from hospitals/I-40

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Single family home near Reynolda Village and Wake Forest University, holiday rental in Winston Salem
Single family home near Reynolda Village and Wake Forest University, holiday rental in Winston Salem
Single family home near Reynolda Village and Wake Forest University, holiday rental in Winston Salem

Single family home near Reynolda Village and Wake Forest University

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Comfortable, covenient, quaint, holiday rental in Winston Salem
Comfortable, covenient, quaint, holiday rental in Winston Salem
Comfortable, covenient, quaint, holiday rental in Winston Salem

Comfortable, covenient, quaint

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!, holiday rental in Winston Salem
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!, holiday rental in Winston Salem
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!, holiday rental in Winston Salem

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Charming Winston-Salem Studio, 3 Mi to Downtown!, holiday rental in Winston Salem
Charming Winston-Salem Studio, 3 Mi to Downtown!, holiday rental in Winston Salem
Charming Winston-Salem Studio, 3 Mi to Downtown!, holiday rental in Winston Salem

Charming Winston-Salem Studio, 3 Mi to Downtown!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Historic West End Hideaway, walk to downtown WS, holiday rental in Winston Salem
Historic West End Hideaway, walk to downtown WS, holiday rental in Winston Salem
Historic West End Hideaway, walk to downtown WS, holiday rental in Winston Salem

Historic West End Hideaway, walk to downtown WS

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Historic Beauty: 5BR Home with Yard Near Hospital, holiday rental in Winston Salem
Historic Beauty: 5BR Home with Yard Near Hospital, holiday rental in Winston Salem
Historic Beauty: 5BR Home with Yard Near Hospital, holiday rental in Winston Salem

Historic Beauty: 5BR Home with Yard Near Hospital

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Deacon Stays: The Brookwood - Walk to WFU, holiday rental in Winston Salem
Deacon Stays: The Brookwood - Walk to WFU, holiday rental in Winston Salem
Deacon Stays: The Brookwood - Walk to WFU, holiday rental in Winston Salem

Deacon Stays: The Brookwood - Walk to WFU

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Privacy And Proximity, holiday rental in Winston Salem
Privacy And Proximity, holiday rental in Winston Salem
Privacy And Proximity, holiday rental in Winston Salem

Privacy And Proximity

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Home away from Home, holiday rental in Winston Salem
Home away from Home, holiday rental in Winston Salem
Home away from Home, holiday rental in Winston Salem

Home away from Home

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Hartman Casita!, holiday rental in Winston Salem
Hartman Casita!, holiday rental in Winston Salem
Hartman Casita!, holiday rental in Winston Salem

Hartman Casita!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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The Sunrise! Close to Wake forest University, holiday rental in Winston Salem
The Sunrise! Close to Wake forest University, holiday rental in Winston Salem
The Sunrise! Close to Wake forest University, holiday rental in Winston Salem

The Sunrise! Close to Wake forest University

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Carolina Cheerful and Charming, holiday rental in Winston Salem
Carolina Cheerful and Charming, holiday rental in Winston Salem
Carolina Cheerful and Charming, holiday rental in Winston Salem

Carolina Cheerful and Charming

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Historical Bungalow Mins From Downtown, Shop, Hosp, holiday rental in Winston Salem
Historical Bungalow Mins From Downtown, Shop, Hosp, holiday rental in Winston Salem
Historical Bungalow Mins From Downtown, Shop, Hosp, holiday rental in Winston Salem

Historical Bungalow Mins From Downtown, Shop, Hosp

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Adorable near UNCSA and Downtown, holiday rental in Winston Salem
Adorable near UNCSA and Downtown, holiday rental in Winston Salem
Adorable near UNCSA and Downtown, holiday rental in Winston Salem

Adorable near UNCSA and Downtown

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Serene 5Bd/4Ba - sleeps 12+ - 5 min to Wake Forest Univ, holiday rental in Winston Salem
Serene 5Bd/4Ba - sleeps 12+ - 5 min to Wake Forest Univ, holiday rental in Winston Salem
Serene 5Bd/4Ba - sleeps 12+ - 5 min to Wake Forest Univ, holiday rental in Winston Salem

Serene 5Bd/4Ba - sleeps 12+ - 5 min to Wake Forest Univ

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Ardmore Gem close to mall and Hospitals, 4bed/3bth, holiday rental in Winston Salem
Ardmore Gem close to mall and Hospitals, 4bed/3bth, holiday rental in Winston Salem
Ardmore Gem close to mall and Hospitals, 4bed/3bth, holiday rental in Winston Salem

Ardmore Gem close to mall and Hospitals, 4bed/3bth

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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West End Stained Glass on Sunset, holiday rental in Winston Salem
West End Stained Glass on Sunset, holiday rental in Winston Salem
West End Stained Glass on Sunset, holiday rental in Winston Salem

West End Stained Glass on Sunset

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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NEW! Beautiful One Level � Close 2 Everything!, holiday rental in Winston Salem
NEW! Beautiful One Level � Close 2 Everything!, holiday rental in Winston Salem
NEW! Beautiful One Level � Close 2 Everything!, holiday rental in Winston Salem

NEW! Beautiful One Level � Close 2 Everything!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Winston-Salem Vacation Rental ~ 3 Mi to Downtown!, holiday rental in Winston Salem
Winston-Salem Vacation Rental ~ 3 Mi to Downtown!, holiday rental in Winston Salem
Winston-Salem Vacation Rental ~ 3 Mi to Downtown!, holiday rental in Winston Salem

Winston-Salem Vacation Rental ~ 3 Mi to Downtown!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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An urban oasis in downtown Winston-Salem, holiday rental in Winston Salem
An urban oasis in downtown Winston-Salem, holiday rental in Winston Salem
An urban oasis in downtown Winston-Salem, holiday rental in Winston Salem

An urban oasis in downtown Winston-Salem

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Luxury tent on lowery mill creek, holiday rental in Winston Salem
Luxury tent on lowery mill creek, holiday rental in Winston Salem
Luxury tent on lowery mill creek, holiday rental in Winston Salem

Luxury tent on lowery mill creek

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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1bedroom home with free parking on premise+pet fee, holiday rental in Winston Salem
1bedroom home with free parking on premise+pet fee, holiday rental in Winston Salem
1bedroom home with free parking on premise+pet fee, holiday rental in Winston Salem

1bedroom home with free parking on premise+pet fee

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Hidden Treasure of the Winston Salem + Pet Fee, holiday rental in Winston Salem
Hidden Treasure of the Winston Salem + Pet Fee, holiday rental in Winston Salem
Hidden Treasure of the Winston Salem + Pet Fee, holiday rental in Winston Salem

Hidden Treasure of the Winston Salem + Pet Fee

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Retreat to affordable house in WinstonSalem+PetFee, holiday rental in Winston Salem
Retreat to affordable house in WinstonSalem+PetFee, holiday rental in Winston Salem
Retreat to affordable house in WinstonSalem+PetFee, holiday rental in Winston Salem

Retreat to affordable house in WinstonSalem+PetFee

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Showing results 1-50 of 229
Frequently Asked Questions about Winston Salem