Vacation rentals in Winston-Salem, NC

191 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Winston-Salem, NC

Guest suite in Winston Salem - Winston-Salem, NC

Guest suite in Winston Salem

Apartment, Winston-Salem

Guest suite in Winston Salem is a apartment in Winston-Salem, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Guest suite in Winston Salem

Guest suite in Winston Salem is a apartment in Winston-Salem, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $533.

From$53/night
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Clarion Pointe Winston – Salem Downtown - Winston-Salem, NC

Clarion Pointe Winston – Salem Downtown

Guest House, Winston-Salem

Clarion Pointe Winston – Salem Downtown is a guest house in Winston-Salem, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Clarion Pointe Winston – Salem Downtown

Clarion Pointe Winston – Salem Downtown is a guest house in Winston-Salem, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free breakfast, free wifi, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $591.

From$75/night
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Cozy 1-bedroom condo in Downtown Winston-Salem, free parking! - Winston-Salem, NC

Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!

Condo, Winston-Salem

Cozy 1-bedroom condo in Downtown Winston-Salem, free parking! is a condo in Winston-Salem, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable…

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About Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!

Cozy 1-bedroom condo in Downtown Winston-Salem, free parking! is a condo in Winston-Salem, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $672.

From$75/night
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Cozy 2 bed room - Winston-Salem, NC

Cozy 2 bed room

Holiday Home, Winston-Salem

Cozy 2 bed room is a holiday home in Winston-Salem, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cozy 2 bed room

Cozy 2 bed room is a holiday home in Winston-Salem, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $825.

From$85/night
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Browse Vacation Rentals with a Pool in Winston-Salem, NC

Add a pool to the search when you want an easy place to cool off between outings.

The Welcoming Winston | 3BR Cozy Home & Pool Table - Winston-Salem, NC

The Welcoming Winston | 3BR Cozy Home & Pool Table

Holiday Home, Winston-Salem

The Welcoming Winston · 3BR Cozy Home & Pool Table is a holiday home in Winston-Salem, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About The Welcoming Winston | 3BR Cozy Home & Pool Table

The Welcoming Winston · 3BR Cozy Home & Pool Table is a holiday home in Winston-Salem, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,188.

From$108/night
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Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK! - Winston-Salem, NC

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

Holiday Home, Winston-Salem

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK! is a holiday home in Winston-Salem, with pet-friendly space and pool access. This stay gives travelers a…

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

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK! is a holiday home in Winston-Salem, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,500.

From$161/night
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The Ardmore Executive Suite - Winston-Salem, NC

The Ardmore Executive Suite

Holiday Home, Winston-Salem

The Ardmore Executive Suite is a holiday home in Winston-Salem, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Ardmore Executive Suite

The Ardmore Executive Suite is a holiday home in Winston-Salem, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free breakfast, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,555.

From$187/night
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The Ardmore Executive Suite - Winston-Salem, NC

The Ardmore Executive Suite

Holiday Home, Winston-Salem

The Ardmore Executive Suite is a holiday home in Winston-Salem, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Ardmore Executive Suite

The Ardmore Executive Suite is a holiday home in Winston-Salem, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,612.

From$190/night
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Best Winston-Salem, NC vacation rentals with parking

Find vacation rentals that make arriving by car easier.

3-bedroom house in charming Winston-Salem Ardmore area - Winston-Salem, NC

3-bedroom house in charming Winston-Salem Ardmore area

Holiday Home, Winston-Salem

3-bedroom house in charming Winston-Salem Ardmore area is a holiday home in Winston-Salem, with parking and room for a group. This stay gives travelers a comfortable base for exploring the…

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About 3-bedroom house in charming Winston-Salem Ardmore area

3-bedroom house in charming Winston-Salem Ardmore area is a holiday home in Winston-Salem, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,073.

From$109/night
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Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably. - Winston-Salem, NC

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Holiday Home, Winston-Salem

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably. is a holiday home in Winston-Salem, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably. is a holiday home in Winston-Salem, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,100.

From$113/night
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Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital! - Winston-Salem, NC

Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!

Holiday Home, Winston-Salem

Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital! is a holiday home in Winston-Salem, with parking and kitchen access. This stay gives travelers a comfortable…

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About Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital!

Recently renovated luxury duplex unit. Short walk to Atrium WF Baptist Hospital! is a holiday home in Winston-Salem, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,332.

From$136/night
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Entire condo in historic downtown Winston-salem building - Winston-Salem, NC

Entire condo in historic downtown Winston-salem building

Condo, Winston-Salem

Entire condo in historic downtown Winston-salem building is a condo in Winston-Salem, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Entire condo in historic downtown Winston-salem building

Entire condo in historic downtown Winston-salem building is a condo in Winston-Salem, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,376.

From$143/night
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Best Pet-Friendly Vacation Rentals in Winston-Salem, NC

Bring your pet along with stays that welcome four-legged travelers.

Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds - Winston-Salem, NC

Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds

Holiday Home, Winston-Salem

Modern 2BR Retreat · 85” TV Ultra-Comfy king Beds is a holiday home in Winston-Salem, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds

Modern 2BR Retreat · 85” TV Ultra-Comfy king Beds is a holiday home in Winston-Salem, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $938.

From$90/night
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3 King Beds | XL TVs | Near Hospital, College & DT - Winston-Salem, NC

3 King Beds | XL TVs | Near Hospital, College & DT

Holiday Home, Winston-Salem

3 King Beds · XL TVs · Near Hospital, College & DT is a holiday home in Winston-Salem, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 3 King Beds | XL TVs | Near Hospital, College & DT

3 King Beds · XL TVs · Near Hospital, College & DT is a holiday home in Winston-Salem, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $940.

From$92/night
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La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA - Winston-Salem, NC

La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

Holiday Home, Winston-Salem

La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA is a holiday home in Winston-Salem, with pet-friendly space. This stay gives travelers a comfortable base for…

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About La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA

La Casita #2 Great location,close to downtown Winston Salem 1 mile from UNCSA is a holiday home in Winston-Salem, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,105.

From$114/night
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3 King Beds Quiet Workspace Near Novant/Wake Forest - Winston-Salem, NC

3 King Beds Quiet Workspace Near Novant/Wake Forest

Holiday Home, Winston-Salem

3 King Beds Quiet Workspace Near Novant/Wake Forest is a holiday home in Winston-Salem, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a…

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About 3 King Beds Quiet Workspace Near Novant/Wake Forest

3 King Beds Quiet Workspace Near Novant/Wake Forest is a holiday home in Winston-Salem, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,416.

From$135/night
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Best Winston-Salem, NC vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Quit, Cozy, Pet Friendly Condo - Winston-Salem, NC

Quit, Cozy, Pet Friendly Condo

Condo, Winston-Salem

Quit, Cozy, Pet Friendly Condo is a condo in Winston-Salem, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Quit, Cozy, Pet Friendly Condo

Quit, Cozy, Pet Friendly Condo is a condo in Winston-Salem, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $901.

From$85/night
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LUX Home - Centrally Located - only minutes to Norvant Health & Historic Salem - Winston-Salem, NC

LUX Home - Centrally Located - only minutes to Norvant Health & Historic Salem

Holiday Home, Winston-Salem

LUX Home - Centrally Located - only minutes to Norvant Health & Historic Salem is a holiday home in Winston-Salem, with parking and kitchen access. This stay gives travelers a comfortable…

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About LUX Home - Centrally Located - only minutes to Norvant Health & Historic Salem

LUX Home - Centrally Located - only minutes to Norvant Health & Historic Salem is a holiday home in Winston-Salem, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,264.

From$128/night
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Charming 2-bedroom apartment in Winston-Salem with WiFi and AC - Winston-Salem, NC

Charming 2-bedroom apartment in Winston-Salem with WiFi and AC

Apartment, Winston-Salem

Charming 2-bedroom apartment in Winston-Salem with WiFi and AC is a apartment in Winston-Salem, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Charming 2-bedroom apartment in Winston-Salem with WiFi and AC

Charming 2-bedroom apartment in Winston-Salem with WiFi and AC is a apartment in Winston-Salem, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,576.

From$149/night
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Historic Carriage House in Walkable Downtown Winston-Salem - Winston-Salem, NC

Historic Carriage House in Walkable Downtown Winston-Salem

Holiday Home, Winston-Salem

Historic Carriage House in Walkable Downtown Winston-Salem is a holiday home in Winston-Salem, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Historic Carriage House in Walkable Downtown Winston-Salem

Historic Carriage House in Walkable Downtown Winston-Salem is a holiday home in Winston-Salem, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,458.

From$153/night
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Our Favorite Family-Friendly Vacation Rentals in Winston-Salem, NC

Plan a trip with stays that give families more room to spread out.

Updated 1BR cottage on private acre+ lot - Winston-Salem, NC

Updated 1BR cottage on private acre+ lot

Holiday Home, Winston-Salem

Updated 1BR cottage on private acre+ lot is a holiday home in Winston-Salem, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Updated 1BR cottage on private acre+ lot

Updated 1BR cottage on private acre+ lot is a holiday home in Winston-Salem, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $796.

From$82/night
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Quaint 2-bedroom cottage with in Winston-Salem two minutes away from Salem lake - Winston-Salem, NC

Quaint 2-bedroom cottage with in Winston-Salem two minutes away from Salem lake

Cottage, Winston-Salem

Quaint 2-bedroom cottage with in Winston-Salem two minutes away from Salem lake is a cottage in Winston-Salem, with parking and room for a group. This stay gives travelers a comfortable…

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About Quaint 2-bedroom cottage with in Winston-Salem two minutes away from Salem lake

Quaint 2-bedroom cottage with in Winston-Salem two minutes away from Salem lake is a cottage in Winston-Salem, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $929.

From$93/night
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Cozy Ardmore Cottage Basement Apartment - Winston-Salem, NC

Cozy Ardmore Cottage Basement Apartment

Holiday Home, Winston-Salem

Cozy Ardmore Cottage Basement Apartment is a holiday home in Winston-Salem, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Ardmore Cottage Basement Apartment

Cozy Ardmore Cottage Basement Apartment is a holiday home in Winston-Salem, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,056.

From$119/night
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Cheerful cottage w/work space near hospitals - Winston-Salem, NC

Cheerful cottage w/work space near hospitals

Holiday Home, Winston-Salem

Cheerful cottage w/work space near hospitals is a holiday home in Winston-Salem, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cheerful cottage w/work space near hospitals

Cheerful cottage w/work space near hospitals is a holiday home in Winston-Salem, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,329.

From$135/night
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