Vacation rentals in Monticello, KY

90 available vacation rental offers

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Best vacation rentals and Airbnb offers in Monticello, KY

Enchanting Glamping Tent on Lake Cumberland - Monticello, KY

Enchanting Glamping Tent on Lake Cumberland

Holiday Home, Monticello

Enchanting Glamping Tent on Lake Cumberland is a holiday home in Monticello, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Enchanting Glamping Tent on Lake Cumberland

Enchanting Glamping Tent on Lake Cumberland is a holiday home in Monticello, 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 $550.

From$79/night
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Dreamy Glamping Tent Near Conley Bottom - Monticello, KY

Dreamy Glamping Tent Near Conley Bottom

Holiday Home, Monticello

Dreamy Glamping Tent Near Conley Bottom is a holiday home in Monticello, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Dreamy Glamping Tent Near Conley Bottom

Dreamy Glamping Tent Near Conley Bottom is a holiday home in Monticello, 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 $568.

From$81/night
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Plush Yome Tucked in the Woods - Monticello, KY

Plush Yome Tucked in the Woods

Holiday Home, Monticello

Plush Yome Tucked in the Woods is a holiday home in Monticello, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Plush Yome Tucked in the Woods

Plush Yome Tucked in the Woods is a holiday home in Monticello, 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, bbq facilities, and non smoking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $698.

From$100/night
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Cozy Tiny Cabin Retreat - Monticello, KY

Cozy Tiny Cabin Retreat

Holiday Home, Monticello

Cozy Tiny Cabin Retreat is a holiday home in Monticello, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Tiny Cabin Retreat

Cozy Tiny Cabin Retreat is a holiday home in Monticello, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $705.

From$101/night
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Vacation rentals with a pool in Monticello, KY

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

Beautiful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #408! - Monticello, KY

Beautiful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #408!

Cabin, Monticello

Beautiful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #408! is a cabin in Monticello, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Beautiful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #408!

Beautiful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #408! is a cabin in Monticello, 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 $1,374.

From$196/night
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Breathtaking 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #418! - Monticello, KY

Breathtaking 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #418!

Cabin, Monticello

Breathtaking 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #418! is a cabin in Monticello, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Breathtaking 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #418!

Breathtaking 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #418! is a cabin in Monticello, 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 $1,374.

From$196/night
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Delightful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #407! - Monticello, KY

Delightful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #407!

Cabin, Monticello

Delightful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #407! is a cabin in Monticello, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Delightful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #407!

Delightful 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #407! is a cabin in Monticello, 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 $1,374.

From$196/night
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Gorgeous 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #409! - Monticello, KY

Gorgeous 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #409!

Cabin, Monticello

Gorgeous 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #409! is a cabin in Monticello, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Gorgeous 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #409!

Gorgeous 1-Bedroom Tiny Home 1/2 Mile from Marina and Boat Ramp #409! is a cabin in Monticello, 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 $1,374.

From$196/night
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Vacation rentals with parking in Monticello, KY

Find vacation rentals that make arriving by car easier.

Special Retreat in Nancy - Monticello, KY

Special Retreat in Nancy

Holiday Home, Monticello

Special Retreat in Nancy is a holiday home in Monticello, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Special Retreat in Nancy

Special Retreat in Nancy is a holiday home in Monticello, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,042.

From$149/night
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Comfy & cozy A Frame 1 mile from Lake Cumberland/Jamestown Marina - Monticello, KY

Comfy & cozy A Frame 1 mile from Lake Cumberland/Jamestown Marina

Cabin, Monticello

Comfy & cozy A Frame 1 mile from Lake Cumberland/Jamestown Marina is a cabin in Monticello, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Comfy & cozy A Frame 1 mile from Lake Cumberland/Jamestown Marina

Comfy & cozy A Frame 1 mile from Lake Cumberland/Jamestown Marina is a cabin in Monticello, 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,158.

From$165/night
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1 mile to Jamestown Marina, 2-bedroom cabin in charming Jamestown, KY - Monticello, KY

1 mile to Jamestown Marina, 2-bedroom cabin in charming Jamestown, KY

Cabin, Monticello

1 mile to Jamestown Marina, 2-bedroom cabin in charming Jamestown, KY is a cabin in Monticello, with parking and room for a group. This stay gives travelers a comfortable base for exploring…

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About 1 mile to Jamestown Marina, 2-bedroom cabin in charming Jamestown, KY

1 mile to Jamestown Marina, 2-bedroom cabin in charming Jamestown, KY is a cabin in Monticello, 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,181.

From$169/night
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Lake it or Leave it! Lake House just one mile from Lake Cumberland Marina - Monticello, KY

Lake it or Leave it! Lake House just one mile from Lake Cumberland Marina

Holiday Home, Monticello

Lake it or Leave it! Lake House just one mile from Lake Cumberland Marina is a holiday home in Monticello, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Lake it or Leave it! Lake House just one mile from Lake Cumberland Marina

Lake it or Leave it! Lake House just one mile from Lake Cumberland Marina is a holiday home in Monticello, 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 $1,347.

From$192/night
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Pet-friendly vacation rentals in Monticello, KY

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

Little blue house on the lake - Monticello, KY

Little blue house on the lake

Holiday Home, Monticello

Little blue house on the lake is a holiday home in Monticello, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Little blue house on the lake

Little blue house on the lake is a holiday home in Monticello, 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 $1,234.

From$176/night
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Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY - Monticello, KY

Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY

Cabin, Monticello

Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY is a cabin in Monticello, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY

Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY is a cabin in Monticello, 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 $1,338.

From$191/night
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Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard! - Monticello, KY

Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!

Cabin, Monticello

Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard! is a cabin in Monticello, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!

Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard! is a cabin in Monticello, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,379.

From$197/night
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Monticello Home w/ Deck & Fire Pit < 1 Mi to Water - Monticello, KY

Monticello Home w/ Deck & Fire Pit < 1 Mi to Water

Holiday Home, Monticello

Monticello Home w/ Deck & Fire Pit < 1 Mi to Water is a holiday home in Monticello, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Monticello Home w/ Deck & Fire Pit < 1 Mi to Water

Monticello Home w/ Deck & Fire Pit < 1 Mi to Water is a holiday home in Monticello, 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 $1,442.

From$206/night
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Vacation rentals with a kitchen in Monticello, KY

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

2 Bedroom Family Cabin #3 3/4 Miles to Cumberland Marina WIFI-NO CLEANING FEE! - Monticello, KY

2 Bedroom Family Cabin #3 3/4 Miles to Cumberland Marina WIFI-NO CLEANING FEE!

Cabin, Monticello

2 Bedroom Family Cabin #3 3/4 Miles to Cumberland Marina WIFI-NO CLEANING FEE! is a cabin in Monticello, with kitchen access and room for a group. This stay gives travelers a comfortable…

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About 2 Bedroom Family Cabin #3 3/4 Miles to Cumberland Marina WIFI-NO CLEANING FEE!

2 Bedroom Family Cabin #3 3/4 Miles to Cumberland Marina WIFI-NO CLEANING FEE! is a cabin in Monticello, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,408.

From$201/night
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Cabin in the Woods @ LakePointe Resort - no cleaning fees! Cabin B - Monticello, KY

Cabin in the Woods @ LakePointe Resort - no cleaning fees! Cabin B

Cabin, Monticello

Cabin in the Woods @ LakePointe Resort - no cleaning fees! Cabin B is a cabin in Monticello, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cabin in the Woods @ LakePointe Resort - no cleaning fees! Cabin B

Cabin in the Woods @ LakePointe Resort - no cleaning fees! Cabin B is a cabin in Monticello, 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 $1,408.

From$201/night
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See the Horses! @ LakePointe Resort - no cleaning fees! - Monticello, KY

See the Horses! @ LakePointe Resort - no cleaning fees!

Cabin, Monticello

See the Horses! @ LakePointe Resort - no cleaning fees! is a cabin in Monticello, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About See the Horses! @ LakePointe Resort - no cleaning fees!

See the Horses! @ LakePointe Resort - no cleaning fees! is a cabin in Monticello, 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 $1,408.

From$201/night
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Two Bedroom Cabin With Covered Back Deck- no cleaning fees! @LakePointe Resort - Monticello, KY

Two Bedroom Cabin With Covered Back Deck- no cleaning fees! @LakePointe Resort

Cabin, Monticello

Two Bedroom Cabin With Covered Back Deck- no cleaning fees! @LakePointe Resort is a cabin in Monticello, with outdoor space, parking, and kitchen access. This stay gives travelers a…

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About Two Bedroom Cabin With Covered Back Deck- no cleaning fees! @LakePointe Resort

Two Bedroom Cabin With Covered Back Deck- no cleaning fees! @LakePointe Resort is a cabin in Monticello, with outdoor 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,408.

From$201/night
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Family-friendly vacation rentals in Monticello, KY

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

Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp - Monticello, KY

Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp

Cottage, Monticello

Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp is a cottage in Monticello, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp

Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp is a cottage in Monticello, 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 $1,254.

From$179/night
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Lake Lover's Paradise! 3 Bed/2 Bath, Walk to Lake on Lake Cumberland! - Monticello, KY

Lake Lover's Paradise! 3 Bed/2 Bath, Walk to Lake on Lake Cumberland!

Holiday Home, Monticello

Lake Lover's Paradise! 3 Bed/2 Bath, Walk to Lake on Lake Cumberland! is a holiday home in Monticello, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Lake Lover's Paradise! 3 Bed/2 Bath, Walk to Lake on Lake Cumberland!

Lake Lover's Paradise! 3 Bed/2 Bath, Walk to Lake on Lake Cumberland! is a holiday home in Monticello, 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 $1,377.

From$197/night
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This charming cozy cottage has a private hot tub, deck for fishing. - Monticello, KY

This charming cozy cottage has a private hot tub, deck for fishing.

Cottage, Monticello

This charming cozy cottage has a private hot tub, deck for fishing. is a cottage in Monticello, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a…

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About This charming cozy cottage has a private hot tub, deck for fishing.

This charming cozy cottage has a private hot tub, deck for fishing. is a cottage in Monticello, with pet-friendly space, pool access, and outdoor 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, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,442.

From$206/night
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Monticello Home w/ Deck & Fire Pit < 1 Mi to Water - Monticello, KY

Monticello Home w/ Deck & Fire Pit < 1 Mi to Water

Cottage, Monticello

Monticello Home w/ Deck & Fire Pit < 1 Mi to Water is a cottage in Monticello, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Monticello Home w/ Deck & Fire Pit < 1 Mi to Water

Monticello Home w/ Deck & Fire Pit < 1 Mi to Water is a cottage in Monticello, with pet-friendly space, outdoor 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 $1,738.

From$206/night
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