Holiday rentals with a pool in New Haven

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

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

Amazing Paradise, King Bed, Pool, BBQ, Pool Table.

Welcome to this amazing GParadise set on 1.62 acres. Situated in a quiet residential neighborhood. These 4 bedrooms home have everything you need. With 1 king bed, 4 queen beds, 1 queen sofa bed, comfortably sleep up to 12 guests. Free parking! Central AC/Heat, fast Wi-Fi, 2 home offices, W/D, open living space, electric fireplace and gourmet kitchen. Enjoy a private fenced inground pool, outdoor shower, propane and wood fire pit, 2 terrace. Relax to the sound of running water of Lindsley brook!

Garden Level Suite with Beautiful Pool

Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

Spacious Cottage Loft

Welcome to the Spacious Cottage Loft! Please enjoy a nice quiet relaxed atmosphere in this unique space. Its a little bit rustic with its shiplap pine and exposed beams. Its a little bit rock and roll with its little music space along with some favorite framed albums hanging on the walls. Very comfy queen size bed. 2 smart TVs (65" up & 55" down) for your entertainment pleasure. Roomy kitchen with brand new appliances. Bath-walk in shower. THIS SPACE IS DESIGNED TO ACCOMMODATE 1-2 GUESTS.

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.

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

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

Dream Home w/ Pool & Basketball Court on 3 Acres

Escape to a private 3-acre retreat with a pool, basketball court, fire pit, and high-end African-inspired interiors. A long, winding driveway offers privacy and space for strolls with strollers or furry friends. Inside, enjoy a double-height living room, chef’s kitchen, cozy den, and a primary suite with pool access. Close to Devil’s Den, Westport beaches & more. Please no parties. Maximum guests is 8. Please note bedroom configuration - the house is set up for families or 4 couples.

Killingworth Estate - Elite Amenities & Finishings

Enjoy your own resort-style oasis in Killingworth/Madison CT! 6 bedrooms (7 beds), in-home theater, private gym, bar, chef's kitchen, sparkling heated saltwater pool and spa, custom pergola in equipped outdoor kitchen w/ pizza oven, outdoor fireplace...all with the highest-end finishes imaginable. Two+ acres with children's playground, soccer field, and climbing wall. Peaceful country setting, yet minutes from Shoreline beaches, acclaimed restaurants, and scenic hiking!

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.

Witsend Farms CT Estate & Pool

Welcome to Witsend Farms A charming 18th century homestead located on 11 acres of picturesque CT countryside. 5 Bdrms, 4.5 baths, 2 ponds, pool, stone courtyard, modern kitchen, dining room, treehouse and gazebo! Perfect for friends and family gatherings Just 2 hours from NYC & 15 minutes from iconic antiques shopping, luxury dining (Mayflower, Winvian, etc), hiking, lakes & fly fishing!