Book Luxury Holiday Rentals in Monroe County

Award-winning homes from £98

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Home spotlights in Monroe County

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Sitting peacefully on the edge of North Twin Lakes, this stylish cottage sets the tone for a restorative retreat in Livingston. Featuring beautiful views, calm rooms and a range of personal touches, you’ll find everything you could need to disconnect and embrace the natural elements.

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866, is steeped in history and rural charm.

The Mountain Glow

The Mountain Glow

  • 6 guests

  • 3 bedrooms

Callicoon, New York

Immersed in a sanctuary of trees, this rustic cabin invites you to enjoy a serene retreat in the Catskill Mountains. Set across five acres and just a six-minute drive from the charming town of Roscoe, there’s everything you could need to feel inspired and renewed by the majestic beauty of this special environment.

Restmeadow Manor

Restmeadow Manor

  • 15 guests

  • 5 bedrooms

Towamensing Township, Carbon County

Just under an hour’s drive from the Pocono mountain range – which happens to be a delight for avid hikers and rafting fanatics alike – this home can be found on a sprawling estate in Pennsylvania. This, of course, means you’re pretty much always surrounded by green lawn, native foliage, ponds and streams, and one of those very ponds sets the scene perfectly for a group picnic or a retreat whenever you want to breakaway with a book for an hour or two.


We selected the top 3% holiday homes in Monroe County Holiday Rentals

Explore the 866 most perfect homes in our collection

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Most popular homes in Monroe County

The Great Harvest

The Great Harvest

  • 34 guests

  • 10 bedrooms

Coolbaugh Township, Monroe County

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

Rise with the Sun

Rise with the Sun

  • 20 guests

  • 8 bedrooms

Pleasant Valley, New York

The Ashokan

The Ashokan

  • 4 guests

  • 2 bedrooms

Glenford, West Hurley

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

Through the Seasons

Through the Seasons

  • 12 guests

  • 5 bedrooms

Tobyhanna Township, Monroe County

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

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Check upcoming rates & availability for Monroe County Holiday Rentals


Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Monroe County. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Monroe County has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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