Holiday rentals with a pool in New Haven

Meeker Hill House - Country Escape w/ Heated Pool

Meeker Hill House is a spacious and chic escape nestled in the heart of Fairfield County, located 90 minutes from NYC and minutes from the hamlet of Redding. Set on a quiet road, this 3 bedrooms and 3.5 baths house is riddled with old world charm. Amenities include a heated pool, fireplaces, fire pit, outdoor dining, screened in porch and a luxury chef's kitchen. Kick back and relax in this calm, stylish space as if in the English Countryside, all under two hours from NYC & under 3 hours fro

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Looking for privacy, seclusion, and direct access to Sleeping Giant State Park right from your back yard? Then look no further! Entire Mid Century home centrally located to many great attractions and colleges. Featuring an open floor plan characterized by large glass windows and open space featuring simplicity and an integration with nature. Access to I-91 or Rt15 are both about 1 mile away, with Yale University and Downtown New Haven about a 20 minute drive. Farmington Canal bike trail-.5 miles

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Once a Pond - time and stress slow down.

If you're looking for a place to escape the City, gather family, work on a book writing project, just breathe, go to the beach or let your dog run, this is the perfect place! The house sits on 4 acres full of wildlife and free of highway noise with a 2 acre pond centrally located in the University area of Fairfield, relatively close to the train station, downtown and the beach. If you need a car for your stay, you can also rent from us via Turo. Looking forward having you as our guest! :)

Artist Retreat in Beautiful Country Setting

Stay at this unique property, owned and designed by a Eu artist, and enjoy the quiet countryside and natural beauty that rural CT has to offer. A large one bedroom studio with an modern fireplace, is equipped with a comfortable king size bed, full bathroom, sauna, indoor resistance pool- available at an extra charge, kitchenette, a workspace, and high-speed internet for seamless remote work. Relax in the evening at your own private outdoor seating area surrounded by the property's charm.

King 1BR Apt with Cozy Den and Luxury Amenities

This gorgeous apt, located in a brand-new luxury building at the center of New Haven’s historic downtown, offers unparalleled comfort, service, and amenities. You can watch a movie on a 65" HDTV, work in one of 5 co-working spaces, or relax at the pool w/ grills and cabanas. Highlights: • Walkable access to Yale • Deep-clean prior to every guest • Coffee, fresh linens, and bathroom essentials • 24/7 fitness center • Rooftop sun terrace + grills • Entertainment lounge w/ bowling alley

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Private Cottage Retreat with Heated Pool

A beautifully serene guest cottage at the historic Stephen Smith House. Located in the gorgeous Connecticut River Valley, in the town of Haddam, the cottage is a private relaxing getaway just 2 hours from NYC and Boston. The special home and bucolic property is situated above a lovely brook, surrounded by mountain views, waterfalls, stone walls, gunite pool, magical gardens and 175 acres of private hiking trails.