Find pet-friendly rentals near Monticello

We found 557 pet-friendly rentals — enter your dates for availability

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September 2025

October 2025

Explore Monticello pet-friendly rentals

Historic, Quaint Bungalow # 157. Spa & Pool

Premier Host

Historic, Quaint Bungalow #157 Pool & Spa

Sleeps 4 · 3 bedrooms · 1 bathroom

Horses and an adjoining secluded cottage overlooking pastures. Private entrance

Premier Host

Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries

Sleeps 4 · 2 bedrooms · 1 bathroom

Welcome to Bluebird Cottage, where you'll be close to award-winning wineries.

Premier Host

Bluebird Cottage A: Near Charlottesville, Wineries: Firepit, Patio, Dogs OK

Sleeps 4 · 1 bedroom · 1 bathroom

Top rated pet-friendly rentals - Monticello

Nestled in the mountainside, this view welcomes you each time you return.

Beautiful cabin in amazing setting!! Super clean and comfortable - great getaway!

Great communication with host, VERY clean and comfortable space! The king bed was comfortable, the hot tub was awesome and the kitchen had everything we needed to prepare meals - highly recommend!!

Lori K.

Stayed Dec 2020

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