Holiday rentals with a pool in Brookfield

4Br Mountain Brook House on 130 acres w/ trails

Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

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!

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 soaking 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 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.

The Dahlia Villa within Westerhall Gardens

This is a quiet retreat where you’re with nature at this beautiful escape. A gorgeous mature garden .Two queen bedrooms, great room, 75 inch TV. Radiant bathroom floor. Outdoor 45,000 gallon salt pool…that’s shared with other property (summer months - POOL IS FOR REGISTERED GUESTS ONLY - NO EXCEPTIONS) Decompress in our sauna. This a no smoking/vaping property. A sprawling 17plus acre estate. Dahlia Villa is a beautiful two bedroom completely independent unit on the estate.

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

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.

Peaceful Light-Filled Guesthouse salt pool/sauna

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Bluewater Lodge at Candlewood Lake

Escape to Candlewood Lake, a serene lakefront retreat in New Milford, CT. Enjoy stunning views of Candlewood Lake and seasonal foliage from the private dock, front porch, or nearly every room. Just minutes from shops and restaurants, it’s the perfect getaway. Explore New Milford, the charming town that inspired Gilmore Girls’ Stars Hollow. ✔ 90-minute drive from NYC ✔ 2.5-hour drive from Boston

Eco Cottage in the Woods

Open again April 1. Come see us. A quiet and private get away, light and airy, surrounded by forest. Birds and deer are visible from the doorways. Relaxing trails start at the cottage. After your walk enjoy the 16x36 unheated gunite pool. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Escape to a Restored New England Antique Milk Barn

A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.