Holiday rentals with a hot tub in Westchester County

Serene Retreat in the Hills w/Jacuzzi

Forget your worries in this spacious and serene space. Only a 50 minute train ride from Grand Central Terminal in downtown New York City, yet be awakened by song birds in the morning. A private road setting, with nature surrounding you. Minutes away from a rail trail, downtown Mount Kisco, restaurants, groceries, shopping and more. Westchester County Parks provide various hiking, farms & golf courses for you to explore. Monthly stays preferred, & certainly welcome the week long travelers.

Magic Red Barn with Heated Salt Pool (opened now)

Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers blooming in June, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool and cedar hot tub. Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

The Monroe | Elegant 2BR/2BA Downtown Stamford

Step into The Monroe, where timeless elegance meets modern comfort in the heart of Downtown Stamford. This thoughtfully designed 2-bedroom, 2-bathroom apartment features a warm and inviting palette of cream, rich browns, and gold accents, creating a serene escape from the bustle of the city. Unwind in a sophisticated living space adorned with designer touches and curated décor. Whether you're relaxing or catching up on work, the Monroe offers a perfect blend of luxury and livability.

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

Once home to actress Misty Rowe (Hee Haw, Brady Bunch, Love Boat), this historic riverside cottage blends rustic charm with modern luxury. Cozy up by the stone fireplace, cook in the chef's kitchen, or unwind on the river-facing deck. Splash in the heated pool, soak in the year-round hot tub, gather by the gazebo, or spot wildlife along the water. Two fire pits, river views, and pure tranquility — just 5 min to downtown Greenwich and 35 min to NYC. Your riverside escape awaits.

Cove Park Sunsets |Hot Tub/Fire Pit/BBQ/EV Charger

Located just a short train ride away from NYC, walking distance to Cove Island Beach Park and Chelsea Piers. Approximatly 1.7 mi from downtown Stamford and train station. Step into our modern, spacious retreat, offering 3 beautifully designed bedrooms, a convenient 1.5 bathroom setup, a private patio with a motorized awning, fire-pit, BBQ grill and hot tub. Apartment is loaded with all the amenities to make your stay enjoyable and convenient. Pets allowed approval required.

Cozy West Point Hide Away and Cadet’s Get Away

Newly renovated basement space in a very quiet secluded neighborhood with a full kitchen, full size bathroom, Fast WiFi, Smart TV, Separate parking, walking distance to Hudson River, Main Street, Bear Mountain State Park, West Point Military Academy and several adventurous hiking trails. For those who like to shop we are located only 20 minutes to the Woodbury Commons and only a 45 minute drive to NYC. Also Stuart International Airport is only a short drive from here.

Hudson Valley Retreat w/Hot Tub 15 mins West Point

If you love nature, quiet, and thoughtful design, this Hudson Valley retreat is for you. Our 3BR, 2BA mid-century modern home sits on a wooded acre in Garrison with a cedar hot tub on the deck and summer lake access. Just 15 minutes to West Point, about an hour from NYC, and minutes to the Appalachian Trail, Cold Spring, and Peekskill. Hike, explore, soak, and cook in our chef’s kitchen—perfect for West Point visits and peaceful Hudson Valley getaways.

Greenwich Sanctuary | 2BR Spa & Massage Retreat

A refined top-floor 2BR sanctuary with private entrance and parking, created for guests seeking elevated comfort and tranquility. Renovated with hardwood floors, a fully equipped kitchen with reverse-osmosis water, and a spa-style bathroom with a jetted soaking tub, bidet, and filtered shower. Unwind in the full-body massage chair and enjoy the naturally calming, healing energy praised by many guests. Ideal for restorative, wellness-focused stays.

Luxury Home w/Hot Tub in Stamford-Pound Ridge

Enjoy a magical long weekend or longer term stay on 3.5 acres of pure nature. Located 50 minutes from NYC by car or 10 minutes drive from Stamford station. *Built in 2020 *Featuring a new luxury HotSprings Hot tub *3.5 acres of wooded privacy *Bioethanol fireplace *3 full en-suite bathrooms *gated rock garden *10 minutes from downtown Stamford, Bedford, Pound Ridge, and Greenwich * Stunning views from every room *dog door to gated area

Retreat | hot tub, mini-golf, fire pit, pickleball

This house makes it a wonderful place for memorable family moments. With its blend of indoor coziness and outdoor tranquility, this home is a haven. We have mini-golf, firepit, hot tub, 2 bbq areas, amazing outdoor entertainment, games and GRASS pickleball court. This charming family home offers the perfect blend of comfort and relaxation. **Long stays will require bi-weekly cleaning which will be charged separately.**

Country Carriage House 9 miles to FIFA World Cup

Spacious eclectic luxurious renovated carriage house on 1 acre with a pool & hot tub, & a separate private 6 seat 60 jet hot tub, sauna, steam room, gas & wood burning fire pits, pool/ping pong table, trampoline & basketball court in a gorgeous quiet suburb of NYC. In 20 minutes you can be enjoying all that NYC & AMERICAN DREAM have to offer & then come back for a sauna & steam. Great small reunion/intimate party space!

Hudson River House - Ferry to NYC

A unique opportunity to sleep and relax on the majestic Hudson River only one hour from the great cultural center of New York City. State Park hiking/biking trails at the end of the block. Fantastic river views. The house and hot tub is completely private. The beach area is shared. There is a completely separate studio apartment unit on the street side of the house with a separate entrance. No shared space.