
Holiday rentals with a pool in Middlesex County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Middlesex County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlesex County rentals with a pool
House rentals with a pool

Homestead Near Mystic, Casinos & Beaches

Corwin House

Spacious Home with Pool in Southold

Gorgeous home with saltwater pool. Steps to beach!

4BR Private Indoor Heated Pool - Lux Mystic Home

East Hampton Rental w/ Pool, Moments to Amenities

Hot Tub and pool Home away from home

North Fork Farmhouse with Saltwater Pool
Condo rentals with a pool

Modern Loft Villa, 1 mile to Mohegan Sun

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Montauk Waterfront Condo w/ Sunset Views

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi

Beautiful Waterview Condo on the North Fork of LI

The Vacay Villa

Deluxe Studio Apt@The Montauk Manor

The N-V ...The Spa at the Norwich Inn.
Destinations to explore
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- Cottage rentals Middlesex County
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- Beach
- Charlestown Beach
- Fairfield Beach
- Yale University
- Southampton Beach
- Foxwoods Resort Casino
- Six Flags New England
- Cooper's Beach, Southampton
- Napeague Beach
- TPC River Highlands
- Ocean Beach Park
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Blue Shutters Beach
- Ninigret Beach
- Silver Sands Beach
- Amagansett Beach
- Groton Long Point Main Beach
- Bushnell Park
- Seaside Beach
- South Jamesport Beach
- Sandy Beach