Holiday rentals in Brewster

Lux Bungalow on the Lake

Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.

Quiet Studio Apartment in Pawling

For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

Mid-Century Escape

This architecturally significant and newly renovated retreat is perfectly situated with incredible privacy and access to hiking trails and in close proximity to the reservoir. An architectural marvel that has been featured in design magazines, this home was built with huge picture windows and glass walls that allow you to embrace the surrounding landscape in a private setting. Close to apple picking, farm stands, shopping, arts, golf, lakes, skiing, hiking, dining (casual & fine) and much more.

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

Beautiful Escape! Hudson Valley House

NO EVENTS OR LAKE ACCESS. Escape the hustle of NYC & unwind at our spacious lake house, nestled near serene lakes, ponds, and lush forests. Perfect for a family getaway, this peaceful retreat offers stunning outdoor scenery and endless adventures. Relax on the deck, hike through picturesque trails and Bike the Empire Rail Trail. Whether you're looking to recharge or enjoy nature with the loved ones, this tranquil oasis is just what you need for a memorable escape, without the far commute.

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Peaceful Modern Lakeview St newly remodeled !

Kick back at this cozy lakeside spot, where everything feels easy and relaxed. Whether you want quiet mornings with coffee, evenings by the water, or days packed with skiing, golf, and good food—you’ve got it all here. The place has a warm, simple style that makes it easy to feel at home. Perfect for couples, friends, or solo travelers looking for a mix of calm and adventure. Out here, the silence feels good—it’s the kind that lets you actually breathe and enjoy the moment.

Stone Cottage Retreat | Sauna + Plunge

Escape to a beautifully restored historic stone cottage on the original Chester Beach estate in the Hudson Valley, minutes from Old Salem Farm. Surrounded by rolling hills, horse pastures, and sunset views, the cottage blends old-world character with warm interiors, exposed beams, and hand-laid stone walls. Unwind in the cedar sauna and cold plunge, cozy up by the fire, and experience one of the Hudson Valley’s most unique countryside stays.

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Cozy Log Cabin Getaway

Adorable log cabin home only one hour and twenty minutes from New York City. Come and enjoy the peace and tranquility of 3 wooded acres while being close to amenities as needed. This true log cabin home features 2 bedrooms, 1.5 bathrooms, a chef's kitchen, vaulted ceilings and exposed beams, a large stone wall that spans both floors of the home, and a wood burning stove that will heat you up on cold winter nights.