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)

Spacious 4 bedroom, oasis with ocean views galore

Scio by the sound is a home that is steps from the water, overlooking the Long Island Sound. Whether you want to lounge by the in ground pool or walk to the beach, you will find your happy place here. The home sleeps up to eleven guests in beautiful Milford, CT with a great location to local beaches and downtown Milford. It is also the perfect place with a large private backyard great for families for vacations or a friends get together or for a local wedding. The possibilities are endless!

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).

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.

Entire Guest House at Fox Pond Farm.

Recently renovated private guest house with access to swimming pool offers sleeping for eleven in four bedrooms. Tastefully decorated with all amenities. Close to Merritt Parkway and train to Manhattan. This is a natural refuge on eleven very private acres. Large private terrace faces westerly for amazing sunsets and offers a "Plein Air" environment for alfresco meals, cocktails and relaxation. An attached vegetable and flower garden with fountain offer a quiet space to relax and reflect.

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

Family Oasis 4bd/2ba Private Yard & POOL!

Just minutes from Quinnipiac University, Choate Rosemary Hall, & Oakdale Theater. This 4- Bedroom, 2-Full Baths home includes 1-master suite, 3-bedrooms, full kitchen, & lots of room for the whole family to spread out. Located on the edge of the wood line, find yourself immersed in the peaceful surroundings with a book on the patio, or go on an adventure in minutes to local attractions. This property has an inground swimming pool (open during season Mid May/June- mid/late Sept)

Cozy, charming retreat in Wallingford.

Welcome to a cozy 1 bedroom condo located in a quiet part of Wallingford and just steps from Oakdale theater and Serafinos Italian restaurant. Cool off at the pool, enjoy coffee on the back deck, tv with lots of streaming options such as Netflix, Hulu, peacock and more. Tennis, basketball courts and pool require key access which is included. Fully stocked kitchen. Coffee and snacks included. Pool is open from 9am until 8pm. Pool is open Memorial Day through Labor Day.