Vacation rentals in Hillsdale, NY

Best vacation rentals and Airbnb offers in Hillsdale, NY

10 ★ 104 reviews

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

Chalet, Hillsdale

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style is a chalet in Hillsdale, with parking and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style is a chalet 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,561.

From$223/night

Show›

10 ★ 16 reviews

Superb Views -- Sunsets, Mountains, Valley

Holiday Home, Hillsdale

Superb Views -- Sunsets, Mountains, Valley is a holiday home in Hillsdale, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Superb Views -- Sunsets, Mountains, Valley

Superb Views -- Sunsets, Mountains, Valley is a holiday home in Hillsdale, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,258.

From$323/night

Show›

10 ★ 14 reviews

Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights

Holiday Home, Hillsdale

Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights is a holiday home in Hillsdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

Read more

About Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights

Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,223.

From$318/night

Show›

10 ★ 5 reviews

Gilbert Ski Chalet | 3 min to Catamount!

Holiday Home, Hillsdale

Gilbert Ski Chalet · 3 min to Catamount! is a holiday home in Hillsdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Gilbert Ski Chalet | 3 min to Catamount!

Gilbert Ski Chalet · 3 min to Catamount! 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,401.

From$343/night

Show›

Family-friendly vacation rentals in Hillsdale, NY

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

10 ★ 60 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,043.

From$292/night

Show›

10 ★ 49 reviews

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 cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,576.

From$368/night

Show›

10 ★ 7 reviews

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

Cottage, Hillsdale

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake is a cottage in Hillsdale, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring…

Read more

About Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake is a cottage 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,520.

From$360/night

Show›

9.8 ★ 19 reviews

Cozy, private and modern Cottage

Cottage, Hillsdale

Cozy, private and modern Cottage is a cottage in Hillsdale, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Cozy, private and modern Cottage

Cozy, private and modern Cottage is a cottage 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,257.

From$180/night

Show›

Pet-friendly vacation rentals in Hillsdale, NY

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

10 ★ 9 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,650.

From$379/night

Show›

10 ★ 1 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,364.

From$338/night

Show›

9.8 ★ 22 reviews

Berkshires dream house

Holiday Home, Hillsdale

Berkshires dream house 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…

Read more

About Berkshires dream house

Berkshires dream house 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,526.

From$361/night

Show›

9.6 ★ 9 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,357.

From$194/night

Show›

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.

10 ★ 24 reviews

Hudson Valley Hideaway - Heated Pool, Lake Access & Fenced Yard - Sleeps 8

Holiday Home, Hillsdale

Hudson Valley Hideaway - Heated Pool, Lake Access & Fenced Yard - Sleeps 8 is a holiday home in Hillsdale, with pet-friendly space, pool access, and room for a group. This stay gives…

Read more

About Hudson Valley Hideaway - Heated Pool, Lake Access & Fenced Yard - Sleeps 8

Hudson Valley Hideaway - Heated Pool, Lake Access & Fenced Yard - Sleeps 8 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,278.

From$611/night

Show›

10 ★ 1 reviews

Beautiful Hudson Valley Country Lake House

Holiday Home, Hillsdale

Beautiful Hudson Valley Country Lake House is a holiday home in Hillsdale, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Beautiful Hudson Valley Country Lake House

Beautiful Hudson Valley Country Lake House is a holiday home in Hillsdale, with pool access 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, pool, parking, free parking, and fireplace.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,735.

From$391/night

Show›

9.8 ★ 138 reviews

5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!

Holiday Home, Hillsdale

5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26! is a holiday home in Hillsdale, with pool access, kitchen access, and room for a group. This stay gives…

Read more

About 5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!

5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26! is a holiday home in Hillsdale, with pool access, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,556.

From$508/night

Show›

9.8 ★ 9 reviews

Stunning views & charming spacious 4-BR home pool and fireplace in Copake Falls

Holiday Home, Hillsdale

Stunning views & charming spacious 4-BR home pool and fireplace in Copake Falls is a holiday home in Hillsdale, with pool access and room for a group. This stay gives travelers a…

Read more

About Stunning views & charming spacious 4-BR home pool and fireplace in Copake Falls

Stunning views & charming spacious 4-BR home pool and fireplace in Copake Falls is a holiday home in Hillsdale, with 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, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,837.

From$691/night

Show›

Vacation rentals with parking in Hillsdale, NY

Find vacation rentals that make arriving by car easier.

10 ★ 61 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,711.

From$244/night

Show›

10 ★ 1 reviews

Copake, NY Mountainview Retreat w/ Fireplace • Near Catamount Ski & Wineries

Holiday Home, Hillsdale

Copake, NY Mountainview Retreat w/ Fireplace · Near Catamount Ski & Wineries is a holiday home in Hillsdale, with pet-friendly space, parking, and a quieter setting. This stay gives…

Read more

About Copake, NY Mountainview Retreat w/ Fireplace • Near Catamount Ski & Wineries

Copake, NY Mountainview Retreat w/ Fireplace · Near Catamount Ski & Wineries is a holiday home in Hillsdale, with pet-friendly space, parking, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,781.

From$397/night

Show›

9.8 ★ 29 reviews

Serene Berkshire Artist's House

Holiday Home, Hillsdale

Serene Berkshire Artist's House is a holiday home in Hillsdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Serene Berkshire Artist's House

Serene Berkshire Artist's House 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,277.

From$325/night

Show›

9.6 ★ 26 reviews

Water-View Home in the Berkshires

Holiday Home, Hillsdale

Water-View Home in the Berkshires is a holiday home in Hillsdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Water-View Home in the Berkshires

Water-View Home in the Berkshires 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,532.

From$362/night

Show›

Vacation rentals with a kitchen in Hillsdale, NY

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

10 ★ 31 reviews

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Holiday Home, Hillsdale

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT is a holiday home in Hillsdale, with parking and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT 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, kids friendly, and kids friendly videos or books.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,949.

From$421/night

Show›

10 ★ 13 reviews

Timberdoodle-a mountainside retreat

Holiday Home, Hillsdale

Timberdoodle-a mountainside retreat is a holiday home in Hillsdale, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Timberdoodle-a mountainside retreat

Timberdoodle-a mountainside retreat is a holiday home 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, free wifi, kitchen, with kitchen, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,942.

From$420/night

Show›

10 ★ 9 reviews

Zen Riverfront studio w/ Spa steam shower, wood stove, SKI Catamount /Butternut

Apartment, Hillsdale

Zen Riverfront studio w/ Spa steam shower, wood stove, SKI Catamount /Butternut is a apartment in Hillsdale, with kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Zen Riverfront studio w/ Spa steam shower, wood stove, SKI Catamount /Butternut

Zen Riverfront studio w/ Spa steam shower, wood stove, SKI Catamount /Butternut is a apartment 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 cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,855.

From$265/night

Show›

9.6 ★ 24 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,246.

From$321/night

Show›