Vacation rentals with a pool in New Haven County

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

Cozy Waterfront Home w/Hot Tub ~ Connecticut River

Relax with the whole family at this quaint waterfront home. This peaceful place to stay will provide the perfect escape for you and your family. Fully renovated and overlooking the CT River, the yard includes an expansive deck with a hot tub and direct river access. The cozy interior features an island kitchen with stainless-steel appliances and quartz countertops. A living room, and dining area overlooking the river, 1st flr bedroom with a full bath, 2 bedrooms and 2 full baths on the 2nd flr.

Amazing Paradise, Seasonal Pool, BBQ, Pool Table.

This is the private upstairs unit of our home. My family lives in the completely separate downstairs unit. You will have your own private entrance, exclusive access to the fenced backyard, seasonal inground pool, patios, and all outdoor amenities. We respect our guests' privacy. Welcome to GParadise, a quiet retreat featuring a fenced seasonal inground pool (officially open on Memorial Day. It's perfect for families, friends, wedding preparations, remote work, extended stays, romantic escapes.

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.

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with large pool, hot-tub, outdoor bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, 5 bedrooms (bedroom 5 has separate entrance by pool and is summer only) plus loft, 3.5 bath plus half bath and outdoor shower by pool. A real oasis! (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed after new year until mid-March)

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

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Classic Red Barn with game room and gym

Enjoy a fun and romantic stay in this classic red barn in the private countryside. The 2-bedroom barn is only available when the main house is unoccupied, so you will have the full run of the beautiful private exterior property. The barn's game room has ping pong, air hockey and foosball tables, and a basketball hoop outside. We also offer a boxing area, weights bench, and fitness mats. In the summer, enjoy the fire pit, grill and pool.

Modern home with a private Heated pool and jacuzzi

In our home-away-from-home, enjoy hotel luxury with more space to feel at home. Our mission is to provide you with more space, less contact, and modern design. Whether for business or leisure, our rooms are perfect for you. We offer keyless entry and exceptional cleaning standards. Conveniently located near Wintergreen Lake and just 12 minutes from Downtown New Haven, get ready to experience the best of New Haven!