Vacation rentals in Hillsdale, NY

Best Vacation rentals and Airbnb offers in Hillsdale, NY

Cozy 1-bedroom studio in serene Great Barrington with AC

Apartment, Hillsdale

Cozy 1-bedroom studio in serene Great Barrington with AC is a apartment in Hillsdale, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for…

Read more

About Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC is a apartment in Hillsdale, with pet-friendly space 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, pet friendly, pets friendly, dryer, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $944.

From$104/night

Show›

Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center

Holiday Home, Hillsdale

Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center is a holiday home in Hillsdale, with pet-friendly space and parking. This stay gives travelers a comfortable…

Read more

About Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center

Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center is a holiday home in Hillsdale, with pet-friendly space and 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,177.

From$116/night

Show›

Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake

Holiday Home, Hillsdale

Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake is a holiday home in Hillsdale, with room for a group. This stay gives travelers a comfortable base for…

Read more

About Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake

Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake is a holiday home in Hillsdale, with 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.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,603.

From$177/night

Show›

Charming Columbia County Farm House

Holiday Home, Hillsdale

Charming Columbia County Farm House is a holiday home in Hillsdale, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Charming Columbia County Farm House

Charming Columbia County Farm House is a holiday home in Hillsdale, 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 $1,941.

From$197/night

Show›

Browse Vacation Rentals with a Pool in Hillsdale, NY

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

MABEL: Michelle and Basquali's Enchanted Loveshack

Holiday Home, Hillsdale

MABEL: Michelle and Basquali's Enchanted Loveshack is a holiday home in Hillsdale, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

Read more

About MABEL: Michelle and Basquali's Enchanted Loveshack

MABEL: Michelle and Basquali's Enchanted Loveshack is a holiday home in Hillsdale, 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, pet friendly, pets friendly, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $908.

From$117/night

Show›

75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub

Holiday Home, Hillsdale

75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub is a holiday home in Hillsdale, with pool access, kitchen access, and a quieter setting. This stay gives…

Read more

About 75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub

75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub is a holiday home in Hillsdale, with pool access, 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, kitchen, with kitchen, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,264.

From$250/night

Show›

Fantastic 2-bedroom house with AC in quaint Hillsdale.

Holiday Home, Hillsdale

Fantastic 2-bedroom house with AC in quaint Hillsdale. is a holiday home in Hillsdale, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable…

Read more

About Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale. is a holiday home in Hillsdale, with pet-friendly space, pool 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,751.

From$624/night

Show›

Modern Retreat - Private Pool & Lake Access

Holiday Home, Hillsdale

Modern Retreat - Private Pool & Lake Access is a holiday home in Hillsdale, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Modern Retreat - Private Pool & Lake Access

Modern Retreat - Private Pool & Lake Access is a holiday home in Hillsdale, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,261.

From$660/night

Show›

Best Hillsdale, NY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

13 Mi to Catamount Mountain Resort: Studio w/ Deck

Apartment, Hillsdale

13 Mi to Catamount Mountain Resort: Studio w/ Deck is a apartment in Hillsdale, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

Read more

About 13 Mi to Catamount Mountain Resort: Studio w/ Deck

13 Mi to Catamount Mountain Resort: Studio w/ Deck is a apartment in Hillsdale, with pet-friendly space, outdoor space, and 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, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,409.

From$142/night

Show›

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View

Apartment, Hillsdale

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View is a apartment in Hillsdale, with outdoor space and parking. This stay gives travelers a comfortable base for…

Read more

About The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View is a apartment in Hillsdale, with outdoor space and 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,716.

From$190/night

Show›

Barn Home & Chicken Farm.

Holiday Home, Hillsdale

Barn Home & Chicken Farm. is a holiday home in Hillsdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Barn Home & Chicken Farm.

Barn Home & Chicken Farm. is a holiday home in Hillsdale, 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 $3,071.

From$328/night

Show›

Charming Copake Falls House

Holiday Home, Hillsdale

Charming Copake Falls House is a holiday home in Hillsdale, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Charming Copake Falls House

Charming Copake Falls House is a holiday home in Hillsdale, 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 $3,645.

From$382/night

Show›

Best Pet-Friendly Vacation Rentals in Hillsdale, NY

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

13 Mi to Catamount Mountain Resort: Studio w/ Deck

Apartment, Hillsdale

13 Mi to Catamount Mountain Resort: Studio w/ Deck is a apartment in Hillsdale, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

Read more

About 13 Mi to Catamount Mountain Resort: Studio w/ Deck

13 Mi to Catamount Mountain Resort: Studio w/ Deck is a apartment in Hillsdale, with pet-friendly space, outdoor space, and 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,518.

From$132/night

Show›

Saltbox-style residence in the Berkshires

Holiday Home, Hillsdale

Saltbox-style residence in the Berkshires is a holiday home in Hillsdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Saltbox-style residence in the Berkshires

Saltbox-style residence in the Berkshires is a holiday home in Hillsdale, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,954.

From$302/night

Show›

Best of the Berkshires + Hot Tub by Evergreen Home

Holiday Home, Hillsdale

Best of the Berkshires + Hot Tub by Evergreen Home is a holiday home in Hillsdale, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Best of the Berkshires + Hot Tub by Evergreen Home

Best of the Berkshires + Hot Tub by Evergreen Home is a holiday home in Hillsdale, 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: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,365.

From$317/night

Show›

Catamount, Zip Line, Private Setting, Book Now!

Holiday Home, Hillsdale

Catamount, Zip Line, Private Setting, Book Now! is a holiday home in Hillsdale, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Catamount, Zip Line, Private Setting, Book Now!

Catamount, Zip Line, Private Setting, Book Now! is a holiday home in Hillsdale, 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 $3,814.

From$380/night

Show›

Best Hillsdale, NY vacation rentals with a kitchen

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

Ghent Getaway, Minutes from Hudson

Apartment, Hillsdale

Ghent Getaway, Minutes from Hudson is a apartment in Hillsdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Ghent Getaway, Minutes from Hudson

Ghent Getaway, Minutes from Hudson is a apartment in Hillsdale, 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 $1,084.

From$115/night

Show›

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness!

Apartment, Hillsdale

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! is a apartment in Hillsdale, with parking, kitchen access, and room for a group. This stay gives travelers a…

Read more

About 2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness!

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! is a apartment in Hillsdale, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,836.

From$200/night

Show›

Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System

Apartment, Hillsdale

Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System is a apartment in Hillsdale, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System

Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System is a apartment in Hillsdale, 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 $2,371.

From$266/night

Show›

Copake Lakes Hidden Treasure

Holiday Home, Hillsdale

Copake Lakes Hidden Treasure is a holiday home in Hillsdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

Read more

About Copake Lakes Hidden Treasure

Copake Lakes Hidden Treasure is a holiday home in Hillsdale, 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 $3,203.

From$350/night

Show›

Our Favorite Family-Friendly Vacation Rentals in Hillsdale, NY

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

Romantic Berkshires Cottage - Stunning Views, Pool

Cottage, Hillsdale

Romantic Berkshires Cottage - Stunning Views, Pool is a cottage in Hillsdale, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Romantic Berkshires Cottage - Stunning Views, Pool

Romantic Berkshires Cottage - Stunning Views, Pool is a cottage in Hillsdale, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,307.

From$246/night

Show›

Deluxe cottage retreat!

Holiday Home, Hillsdale

Deluxe cottage retreat! is a holiday home in Hillsdale, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Deluxe cottage retreat!

Deluxe cottage retreat! is a holiday home in Hillsdale, 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 $2,615.

From$269/night

Show›

Twin Maple Farm: Charming Modern Farmhouse

Holiday Home, Hillsdale

Twin Maple Farm: Charming Modern Farmhouse is a holiday home in Hillsdale, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Twin Maple Farm: Charming Modern Farmhouse

Twin Maple Farm: Charming Modern Farmhouse is a holiday home in Hillsdale, 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,545.

From$356/night

Show›

Stylish 3 Bedroom Cottage located in a Picturesque Lake community

Cottage, Hillsdale

Stylish 3 Bedroom Cottage located in a Picturesque Lake community is a cottage in Hillsdale, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

Read more

About Stylish 3 Bedroom Cottage located in a Picturesque Lake community

Stylish 3 Bedroom Cottage located in a Picturesque Lake community is a cottage in Hillsdale, 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, free wifi, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,656.

From$394/night

Show›