Photo by Brandon Miller

Middlebury rentals with pool

We found 34 rentals with pool — enter your dates for availability

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September 2025

October 2025

Explore Middlebury rentals with pools

5 bedroom, 14 acre private estate

Sleeps 8 · 5 bedrooms · 3+ bathrooms

double ceiling height Living rm w/ skylights, 85"TV and wood burning fireplace

Premier Host

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

Sleeps 7 · 3 bedrooms · 2+ bathrooms

5,100 Sq. Ft. Swiss Chalet-sixteen beautiful, private acres-Perfect for Holidays

Premier Host

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Sleeps 12 · 5 bedrooms · 3+ bathrooms

Spectacular Country Estate (see VIDEO in the navigation bar)

100% WASHINGTON! PoshPadsCT "SUNNY RIDGE" 8-BR Estate, Heated Pool, BBQ, Magical

Sleeps 16 · 8 bedrooms · 7+ bathrooms

Top rated rentals with pools - Middlebury

Gunite pool with full sun exposure, pool floats, and toys for the whole family

Family fun

We had a mixed age group and this was the ideal holiday place for us. Lots of activities onsite, from the pool to the toy room. Great inside and outside group eating options. Then everyone could retire to their separate sleeping quarters. Perfect! Diligent thoughtful owners. Would recommend.

Sally R.

Stayed July 2023

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