Vacation rentals in Craryville, NY

Best Vacation rentals and Airbnb offers in Craryville, NY

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

Holiday Home, Craryville

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

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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 Craryville, 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 $1,173.

From$116/night

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MABEL: Michelle and Basquali's Enchanted Loveshack

Holiday Home, Craryville

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

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About MABEL: Michelle and Basquali's Enchanted Loveshack

MABEL: Michelle and Basquali's Enchanted Loveshack is a holiday home in Craryville, 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 $907.

From$117/night

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13 Mi to Catamount Mountain Resort: Studio w/ Deck

Apartment, Craryville

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

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

13 Mi to Catamount Mountain Resort: Studio w/ Deck is a apartment in Craryville, 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

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13 Mi to Catamount Mountain Resort: Studio w/ Deck

Apartment, Craryville

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

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

13 Mi to Catamount Mountain Resort: Studio w/ Deck is a apartment in Craryville, 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

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Browse Vacation Rentals with a Pool in Craryville, NY

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

Lakefront Catskills Couples' Escape w/ Pool Access

Cabin, Craryville

Lakefront Catskills Couples' Escape w/ Pool Access is a cabin in Craryville, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Lakefront Catskills Couples' Escape w/ Pool Access

Lakefront Catskills Couples' Escape w/ Pool Access is a cabin in Craryville, 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 $2,502.

From$252/night

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Fantastic 2-bedroom house with AC in quaint Hillsdale.

Holiday Home, Craryville

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

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

Fantastic 2-bedroom house with AC in quaint Hillsdale. is a holiday home in Craryville, 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

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Modern Retreat - Private Pool & Lake Access

Holiday Home, Craryville

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

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About Modern Retreat - Private Pool & Lake Access

Modern Retreat - Private Pool & Lake Access is a holiday home in Craryville, 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

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Hudson Valley GetAway: Great for Skiing, family holidays and summers by the pool

Holiday Home, Craryville

Hudson Valley GetAway: Great for Skiing, family holidays and summers by the pool is a holiday home in Craryville, with pool access, kitchen access, and room for a group. This stay gives…

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About Hudson Valley GetAway: Great for Skiing, family holidays and summers by the pool

Hudson Valley GetAway: Great for Skiing, family holidays and summers by the pool is a holiday home in Craryville, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,714.

From$950/night

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Best Craryville, NY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Ghent Getaway, Minutes from Hudson

Apartment, Craryville

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

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About Ghent Getaway, Minutes from Hudson

Ghent Getaway, Minutes from Hudson is a apartment in Craryville, 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

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Nature Retreat Near Prospect Lake

Holiday Home, Craryville

Nature Retreat Near Prospect Lake is a holiday home in Craryville, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Nature Retreat Near Prospect Lake

Nature Retreat Near Prospect Lake is a holiday home in Craryville, with parking, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,089.

From$274/night

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Charming Berkshire Bungalow: Deck, Firepit, Stargazing

Holiday Home, Craryville

Charming Berkshire Bungalow: Deck, Firepit, Stargazing is a holiday home in Craryville, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Charming Berkshire Bungalow: Deck, Firepit, Stargazing

Charming Berkshire Bungalow: Deck, Firepit, Stargazing is a holiday home in Craryville, 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, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,593.

From$277/night

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Barn Home & Chicken Farm.

Holiday Home, Craryville

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

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About Barn Home & Chicken Farm.

Barn Home & Chicken Farm. is a holiday home in Craryville, 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

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Best Pet-Friendly Vacation Rentals in Craryville, NY

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

Cozy 1-bedroom studio in serene Great Barrington with AC

Apartment, Craryville

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

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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 Craryville, 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

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Hudson Victorian - Walkable to Warren St

Holiday Home, Craryville

Hudson Victorian - Walkable to Warren St is a holiday home in Craryville, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Hudson Victorian - Walkable to Warren St

Hudson Victorian - Walkable to Warren St is a holiday home in Craryville, 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 $2,496.

From$235/night

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Charming home on acreage, 10 mins to Hudson

Holiday Home, Craryville

Charming home on acreage, 10 mins to Hudson is a holiday home in Craryville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming home on acreage, 10 mins to Hudson

Charming home on acreage, 10 mins to Hudson is a holiday home in Craryville, 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 $2,234.

From$252/night

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Saltbox-style residence in the Berkshires

Holiday Home, Craryville

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

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About Saltbox-style residence in the Berkshires

Saltbox-style residence in the Berkshires is a holiday home in Craryville, 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

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Best Craryville, NY vacation rentals with a kitchen

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

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

Apartment, Craryville

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

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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 Craryville, 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

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Pondfront Gem Minutes from Hudson’s Best Shops & Cafes | The Stillwater House

Holiday Home, Craryville

Pondfront Gem Minutes from Hudson’s Best Shops & Cafes · The Stillwater House is a holiday home in Craryville, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Pondfront Gem Minutes from Hudson’s Best Shops & Cafes | The Stillwater House

Pondfront Gem Minutes from Hudson’s Best Shops & Cafes · The Stillwater House is a holiday home in Craryville, 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 $3,059.

From$299/night

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Copake Lakes Hidden Treasure

Holiday Home, Craryville

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

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About Copake Lakes Hidden Treasure

Copake Lakes Hidden Treasure is a holiday home in Craryville, 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 $3,201.

From$350/night

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Charming Copake Falls House

Holiday Home, Craryville

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

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About Charming Copake Falls House

Charming Copake Falls House is a holiday home in Craryville, 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

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Our Favorite Family-Friendly Vacation Rentals in Craryville, NY

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

Berkshire Mountain Cottage: in the Heart of the Berkshires

Cottage, Craryville

Berkshire Mountain Cottage: in the Heart of the Berkshires is a cottage in Craryville, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Berkshire Mountain Cottage: in the Heart of the Berkshires

Berkshire Mountain Cottage: in the Heart of the Berkshires is a cottage in Craryville, 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 $2,096.

From$220/night

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Romantic Berkshires Cottage - Stunning Views, Pool

Cottage, Craryville

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

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About Romantic Berkshires Cottage - Stunning Views, Pool

Romantic Berkshires Cottage - Stunning Views, Pool is a cottage in Craryville, 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

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Deluxe cottage retreat!

Holiday Home, Craryville

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

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About Deluxe cottage retreat!

Deluxe cottage retreat! is a holiday home in Craryville, 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

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Stylish 3 Bedroom Cottage located in a Picturesque Lake community

Cottage, Craryville

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

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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 Craryville, 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 $3,654.

From$394/night

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