Vacation rentals in New Windsor, MD

174 available vacation rental offers

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Best vacation rentals and Airbnb offers in New Windsor, MD

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV - New Windsor, MD

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Holiday Home, New Windsor

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV is a holiday home in New Windsor. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV is a holiday home in New Windsor. 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $651.

From$93/night
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Songbird Cottage 3b, sleeps 6 - New Windsor, MD

Songbird Cottage 3b, sleeps 6

Holiday Home, New Windsor

Songbird Cottage 3b, sleeps 6 is a holiday home in New Windsor, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Songbird Cottage 3b, sleeps 6

Songbird Cottage 3b, sleeps 6 is a holiday home in New Windsor, 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $866.

From$124/night
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Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg - New Windsor, MD

Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg

Country House, New Windsor

Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg is a country house in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring…

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About Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg

Charming Farmhouse Getaway With Stunning Mountain Views, Near Gettysburg is a country house in New Windsor, with 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $971.

From$139/night
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cozy guest room with private bath kitchenette - New Windsor, MD

cozy guest room with private bath kitchenette

Holiday Home, New Windsor

cozy guest room with private bath kitchenette is a holiday home in New Windsor, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the…

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About cozy guest room with private bath kitchenette

cozy guest room with private bath kitchenette is a holiday home in New Windsor, 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, washer, dryer, family friendly, and kids toys.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,068.

From$153/night
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Vacation rentals with a pool in New Windsor, MD

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

Resort studio apartment with private hot tub, fire pit, gym, and access to pool. - New Windsor, MD

Resort studio apartment with private hot tub, fire pit, gym, and access to pool.

Apartment, New Windsor

Resort studio apartment with private hot tub, fire pit, gym, and access to pool. is a apartment in New Windsor, with pool access. This stay gives travelers a comfortable base for exploring…

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About Resort studio apartment with private hot tub, fire pit, gym, and access to pool.

Resort studio apartment with private hot tub, fire pit, gym, and access to pool. is a apartment in New Windsor, with 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, gym, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,079.

From$154/night
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Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit - New Windsor, MD

Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit

Country House, New Windsor

Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit is a country house in New Windsor, with pool access and kitchen access. This stay gives travelers a comfortable base…

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About Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit

Secondary Suite In An Amazing Farmhouse with Swimming Pool and FirePit is a country house in New Windsor, with pool access 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, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,527.

From$218/night
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Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm! - New Windsor, MD

Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm!

Apartment, New Windsor

Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm! is a apartment in New Windsor, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm!

Kiwi Berry Farmette, Gardens, Seasonal Pool & Guest Suite at Wild Juniper Farm! is a apartment in New Windsor, with pool access 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,582.

From$226/night
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Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat - New Windsor, MD

Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat

Holiday Home, New Windsor

Backyard Oasis · Swim Spa, Fire Pit & Relaxing Outdoor Retreat is a holiday home in New Windsor, with pool access and a quieter setting. This stay gives travelers a comfortable base for…

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About Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat

Backyard Oasis · Swim Spa, Fire Pit & Relaxing Outdoor Retreat is a holiday home in New Windsor, with pool 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: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,843.

From$406/night
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Vacation rentals with parking in New Windsor, MD

Find vacation rentals that make arriving by car easier.

Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square. - New Windsor, MD

Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square.

Apartment, New Windsor

Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square. is a apartment in New Windsor, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square.

Quiet 1-Bedroom Suite in the Country, 2 Mi. from Gettysburg Square. is a apartment in New Windsor, 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 $653.

From$93/night
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Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown - New Windsor, MD

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Holiday Home, New Windsor

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown is a holiday home in New Windsor, with parking. This stay gives travelers a comfortable base for exploring the…

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About Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown is a holiday home in New Windsor, 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 wifi, parking, paid parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,184.

From$132/night
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Peaceful Getaway w/ Countryside Views in Upperco - New Windsor, MD

Peaceful Getaway w/ Countryside Views in Upperco

Holiday Home, New Windsor

Peaceful Getaway w/ Countryside Views in Upperco is a holiday home in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Peaceful Getaway w/ Countryside Views in Upperco

Peaceful Getaway w/ Countryside Views in Upperco is a holiday home in New Windsor, 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 $1,294.

From$185/night
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A Sentimental Journey - New Windsor, MD

A Sentimental Journey

B & B, New Windsor

A Sentimental Journey is a b & b in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About A Sentimental Journey

A Sentimental Journey is a b & b in New Windsor, 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 breakfast, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $872.

From$112/night
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Pet-friendly vacation rentals in New Windsor, MD

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

Cozy Guesthouse in Woodstock, MD - New Windsor, MD

Cozy Guesthouse in Woodstock, MD

Cabin, New Windsor

Cozy Guesthouse in Woodstock, MD is a cabin in New Windsor, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Guesthouse in Woodstock, MD

Cozy Guesthouse in Woodstock, MD is a cabin in New Windsor, with pet-friendly space, pool access, 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, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,201.

From$172/night
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Quiet, Safe Nest-Minutes to Everything - New Windsor, MD

Quiet, Safe Nest-Minutes to Everything

Holiday Home, New Windsor

Quiet, Safe Nest-Minutes to Everything is a holiday home in New Windsor, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Quiet, Safe Nest-Minutes to Everything

Quiet, Safe Nest-Minutes to Everything is a holiday home in New Windsor, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,308.

From$187/night
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Rural & Historic Detour Escape w/ Horses On-Site! - New Windsor, MD

Rural & Historic Detour Escape w/ Horses On-Site!

Holiday Home, New Windsor

Rural & Historic Detour Escape w/ Horses On-Site! is a holiday home in New Windsor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Rural & Historic Detour Escape w/ Horses On-Site!

Rural & Historic Detour Escape w/ Horses On-Site! is a holiday home in New Windsor, 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 $1,699.

From$243/night
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Vacation rentals with a kitchen in New Windsor, MD

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

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown - New Windsor, MD

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Apartment, New Windsor

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown is a apartment in New Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown is a apartment in New Windsor, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $935.

From$134/night
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Recently remodeled 2 Bedroom apartment in Hanover-Close to Gettysburg and York - New Windsor, MD

Recently remodeled 2 Bedroom apartment in Hanover-Close to Gettysburg and York

Apartment, New Windsor

Recently remodeled 2 Bedroom apartment in Hanover-Close to Gettysburg and York is a apartment in New Windsor, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Recently remodeled 2 Bedroom apartment in Hanover-Close to Gettysburg and York

Recently remodeled 2 Bedroom apartment in Hanover-Close to Gettysburg and York is a apartment in New Windsor, 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 $1,044.

From$149/night
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Remodeled 2 BR 2nd Fl Apartment in Hanover - New Windsor, MD

Remodeled 2 BR 2nd Fl Apartment in Hanover

Apartment, New Windsor

Remodeled 2 BR 2nd Fl Apartment in Hanover is a apartment in New Windsor, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Remodeled 2 BR 2nd Fl Apartment in Hanover

Remodeled 2 BR 2nd Fl Apartment in Hanover is a apartment in New Windsor, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,044.

From$149/night
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Relax with Sunset View - New Windsor, MD

Relax with Sunset View

Holiday Home, New Windsor

Relax with Sunset View is a holiday home in New Windsor, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Relax with Sunset View

Relax with Sunset View is a holiday home in New Windsor, with 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: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,960.

From$280/night
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Family-friendly vacation rentals in New Windsor, MD

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

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA - New Windsor, MD

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Cottage, New Windsor

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA is a cottage in New Windsor, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA is a cottage in New Windsor, 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $987.

From$141/night
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A cozy and spacious house In the heart of Hereford county .Comfortable living . - New Windsor, MD

A cozy and spacious house In the heart of Hereford county .Comfortable living .

Holiday Home, New Windsor

A cozy and spacious house In the heart of Hereford county .Comfortable living . is a holiday home in New Windsor, with kitchen access. This stay gives travelers a comfortable base for…

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About A cozy and spacious house In the heart of Hereford county .Comfortable living .

A cozy and spacious house In the heart of Hereford county .Comfortable living . is a holiday home in New Windsor, with 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,106.

From$158/night
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Farmhouse on River, 12 Miles to Liberty Mountain - New Windsor, MD

Farmhouse on River, 12 Miles to Liberty Mountain

Cottage, New Windsor

Farmhouse on River, 12 Miles to Liberty Mountain is a cottage in New Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Farmhouse on River, 12 Miles to Liberty Mountain

Farmhouse on River, 12 Miles to Liberty Mountain is a cottage in New Windsor, 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 $2,670.

From$316/night
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