Holiday rentals with a hot tub in Fairfield

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

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

Beach Haven - waterfront, near Yale, sunsets

Everything you need for an amazing vacation, year-round, in our comfortable home right on the beach! Walk out the back door and dip your toes in the sand and in Long Island Sound. Enjoy spectacular views from the back patio, sun room, and most rooms in the house. Watch the sunset while soaking in the hot tub. Sit by the gas fireplace with a book. Stroll along the lovely nearby sea wall. 10-minute drive to Yale and all downtown New Haven has to offer. 5-minute drive to Lighthouse Point Park.

The Hilltop Harborview

Guests will immediately walk past spacious hot tub into a comfortable sunroom where you’ll watch the most colorful, water view sunsets Long Island has to offer! This one of a kind offers a sprawling layout that has 3 queen size bedrooms and 1 king . We can also provide an air mattress for an additional guest. There is a kitchen equipped with stove, oven, dishwasher and washer and dryer! This beautiful walking Village has so much to offer! We do allow dogs with prior notice with a $65/dog.

1BR Guest Apt. Suite /full bath, kitchen -Pool/Spa

Private Apartment on 3-Acre Retreat | Heated Gunite Pool, Spa & Terrace. -Near Westport & NYC. Experience peace & privacy at this comfortable, 624sqft. apartment, tucked into a beautifully landscaped 3-acre retreat. With a private entrance, furnished terrace, and access to a shared heated 50-foot gunite pool & spa, this serene getaway is ideal for rest and recharge. It features a California king bed, sleeper couch, a kitchen and a bathroom. Washer & dryer are available in the pool house.

Riverfront Cottage-Pool-Hot Tub-Fireplace 35m>NYC

Once home to actress Misty Rowe (Hee Haw, Brady Bunch, Love Boat), this historic riverside cottage combines rustic elegance with modern comfort. Relax by the stone fireplace, cook in the full kitchen, or step onto the river-facing deck to enjoy peaceful views. Outside, unwind in the heated pool or year-round hot tub, gather by the gazebo, or spot wildlife along the river. Utilize the fire pits and more. A tranquil retreat just 5 minutes from downtown Greenwich and 35 minutes from NYC.

The Magic Red Barn with Heated Salt Pool

Experience countryside magic just one hour from NYC! Enjoy nature’s wonderland, nearby farmers’ markets, and scenic trails. Indulge in our heated saltwater pool for a perfect retreat. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn featuring: 1 king, 2 queen, 1 toddler bed, full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests seeking escape. Enjoy complete privacy—no other guests. Fiber optic Wi-Fi.

3BR, Wildermere Beach, Animal Friendly, Fire Pit

Welcome to your perfect beach getaway in Milford, CT! This stylish, remodeled, fully equipped 3-bedroom retreat offers everything you need for a relaxing stay. Sleep comfortably with a king, queen, and full bed, and enjoy the outdoor deck, jacuzzi, and fire pit for ultimate unwinding. A wagon stocked with beach gear, sand toys, and games makes trips to Wildermere Beach—just a short walk away—effortless. Book now for the perfect mix of comfort, convenience, and coastal charm!

Cozy 1 Bd Private Entrance In-law Suite & Hot Tub

Charming Getaway in Norwalk, CT - Discover comfort and convenience in this cozy low ceiling short-term rental located just 5 minutes from local markets, dining spots, Norwalk River Valley Trail, Norwalk Hospital and shopping centers. Perfect for single travelers, work related or weekend adventurers, this space offers a warm, inviting atmosphere with modern amenities. Enjoy easy access to local attractions and scenic spots, the perfect base for exploring coastal Connecticut!

Oceanfront Beach House w/ Private Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Modern Beach Getaway

This 4 bedroom, 3 bathroom vacation rental in Milford, CT, boasts beautiful hardwood floors, high ceilings, and an open-concept living area perfect for entertaining guests. Each bedroom is tastefully decorated, and the fenced-in private yard features blue stone patio, hot tub and gas firepit area. The rental is located across the street from a private beach and is a short drive from local shops and restaurants, making it the ideal spot for a summer getaway.

Casa Yamagoya

A beautiful mid-century retreat tucked in the hills of Connecticut. Designed and built by a Yale architect who studied under Louis Kahn, and Frank Llyod Wright. With beams that stretch the width of the house and gorgeous pine ceilings. This house is a true gem. Positioned on a ridge at the edge of a secluded state park complete with hiking trails, and bucolic vistas. The house is reminiscent of the Yamagoya, Japanese mountain Huts. IG: @casa_yamagoya