Vacation rentals with a pool in Milford

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)

Shoreline Carriage House

Overlooking acres of salt marsh and distant views of Long Island Sound, this cozy one-bedroom carriage house is perfect for a weekend (or week!) away. The Carriage House boasts access to the pool, a quick 3-5 minute walk to gorgeous beaches, a short drive or bike to restaurants and breweries, and a charming historic downtown. If you are in the mood to stay in (we totally get it), the space includes a brand new queen-sized bed, comfy couch, smart TV and a deck to enjoy the view and sea breeze.

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

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!

3‑Acre Weston Retreat w/ Pool & Basketball Court

Private 3-acre retreat in Weston, CT, featuring a heated seasonal pool, full basketball court, gas fire pit, and expansive wooded grounds. The dramatic double-height great room showcases soaring windows that bring the outdoors inside, while curated African artwork adds warmth and character throughout. Enjoy privacy, nature, and easy access to Compo Beach, Devil's Den, charming New England towns, and NYC. No children under 5. Maximum 8 registered guests. No early check-in. Strictly no parties.

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.

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

Sunny Days w/ Lakeview, seasonal Pool, Hot Tub

Set in the heart of Connecticut’s beloved lake country, this home offers a 4 season year-round escape where the water is always calling. Spend warm days boating, swimming, and fishing, or simply relaxing by the shoreline. As the seasons shift, the lake becomes just as magical—surrounded by fall colors or turning into a peaceful winter retreat. No matter when you visit, this lakefront getaway invites you to slow down, unwind, and enjoy the timeless charm of life by the water.

Lovely Country Retreat:

This beautifully renovated country house is set on 2 acres with a pool in the summer, ( heated , additional charge) ,outdoor gas BBQ, playground & treehouse set back on a quiet, circular road. The house sleeps up to 8 people, has a playroom, movie theatre and is ideal for 2 families traveling with children. Surrounded by bucolic scenery it provides the best blend of country living and fun family activities. If you are looking for a special place, only 1 1/2 h. from NYC

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!

Charming Historic Cottage in the Redwoods

Travel back in time to Marchant Farm and enjoy an authentic farm life experience in the historic, newly restored Sunflower Cottage. Whether you need a place to recharge or to reconnect with nature, you will find it here. Relax and unwind in the stunning floor to ceiling cedar living area. With 2 air conditioned bedrooms, each with full beds, and the children's magical loft space with two twin beds and play area.