New Haven featuring a river or creek and kayaking or canoeing as well as a couple

New Haven County rentals with pool

We found 156 rentals with pool — enter your dates for availability

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September 2025

14

October 2025

Explore New Haven County rentals with pools

Room

Cozy 3 bedroom minutes from Yale and the beach

Sleeps 6 · 3 bedrooms · 1 bathroom

Indoor pool that can be heated!

Luxury 4-bedroom House with Indoor Pool & Picturesque Backyard w/Grill & Firepit

Sleeps 10 · 4 bedrooms · 2+ bathrooms

Fire Pit Seating Area

Premier Host

Peaceful Oasis in Naugatuck - Charming 3-Bedroom Home with serene backyard.

Sleeps 8 · 3 bedrooms · 1 bathroom

Aerial view

Premier Host

Gorgeous four bedroom direct waterfront getaway in Branford, CT 5-Star Rating

Sleeps 8 · 4 bedrooms · 3+ bathrooms

View of the estuary, from glass enclosed dining room and living room(High tide)

Premier Host

Last minute cancellation Labor Day 30% disc. Beautiful Ocean, botanical Garden.

Sleeps 4 · 2 bedrooms · 1 bathroom

Find spaces that suit your style

Holiday Rental options in New Haven County

Pet-friendly holiday rentals in New Haven County

Ski holiday rentals in New Haven County

Holiday rentals with spa pool in New Haven County

Oceanfront holiday rentals in New Haven County

Mountain holiday rentals in New Haven County

Family-friendly holiday rentals in New Haven County

Lake holiday rentals in New Haven County

Beach holiday rentals in New Haven County

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