Holiday rentals with a pool in New Milford

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

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

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, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool (summer) and cedar soaking tub (winter). 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.

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

PLEASE READ ALL HOUSE RULES PRIOR TO INQUIRIES AND BOOKINGS! 1 night/longer stays can be accommodated upon request and calendar availability. “Home Is Where The Heart Is”. If you love tranquility and coziness combined with sophistication and traditional rural charm, this is the place for your stay (only 4 miles from Beacon). The ground floor apartment with a private entrance (located around the back in a private house) includes a living room, full kitchen, full bathroom and Queen bedroom

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Lovely country house; stunning view

This 100 year-old home on 83 acres overlooks a beautiful meadow, surrounded by dogwood and maple trees -- breathtaking in spring and fall. The saline pool is open generally between April and October, and surrounded by an abundance of flowers. In the cooler months, an atmospheric wood-burning fireplace makes the cottage cozy. This property is the subject of a book A FIELD OF MY OWN: A Memoir of Place. Please note that 35-40% of the price is fees and taxes from this site.

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.

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Welcome to Hudson Valley Hideaway — a Modern stylish family friendly home in Beacon, NY, just 1.5 miles from downtown and the train. Bright, stylish home with 4 bedrooms, w/ 1 King bedroom, 2 queens and a Twin XL, stocked kitchen, and cozy living spaces. Enjoy a private fenced backyard retreat with pool, hot tub, fire pit, and grill. Perfect for relaxing or exploring the Hudson Valley, with easy access to Route 84 and local attractions.

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

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.