Dive Into Summer: Hudson Valley Weekend Retreats with Pools

Beat the heat this summer with a staycation at remote and tranquil short-term rentals located right here in the Hudson Valley. Whether you’re looking for a romantic weekend for two or a group getaway, these peaceful, pool-equipped pads offer a local retreat from your day-to-day. 

Private Guest Cottage, Woodstock, NY

A sweet little guest cottage for two features a vaulted ceiling and a bright large space overlooking the garden and heated pool, featuring a private guest seating area, fire pit, and grill. Enjoy this secluded cottage on five acres with views of the Ashokan Reservoir, only minutes from the village of Woodstock up a winding, steep mountain road. 

Modern Upstate Cabin, Red Hook, NY

This elegantly designed, modern glass and wood cabin offers elegant modern details – including a soaking egg tub, outdoor shower, year-round heated pool, and glass “solarium” as one of the bedrooms.  You will fall in love with the 360-degree breathtaking views of the surrounding trees and foliage, the tree-height sleeping loft, and the hammocks ready for reading and napping.  

The Antique Stone House, Kingston, NY

A private guesthouse in the historic Antique Stone House built in 1810 with room for up to four guests. Walkable location to the historic city of Kingston, close to both the Stockade District and the Waterfront. Completely private even though it’s part of the larger house, your stay includes the use of a large built-in pool and hot tub, ample backyard with plants and flowers, and a barbeque area. 

1869 Hand-Hewn Barn, Woodstock, NY

This hemlock Schoharie dairy barn was recently disassembled and moved to the old Downer Family farm in Woodstock. The one-of-a-kind space is an artist’s dream – featuring an entirely open floor plan, with exposed beams, stained glass, and whimsical artwork throughout.  A three-story silo offers an impressive backdrop to the incredible outdoor living including a fire pit, pool, hot tub, sauna, gym, and expansive yard.

Work from Home in Modern Luxury, Kingston, NY 

This brand new modern house has it all and blends seamlessly into the natural landscape. Need a work-from-home escape? You’ll have two separate office options.  But it’s the outdoor areas that will really draw you in –  enjoy a glass of wine on 600+ square feet of deck space, soak in the heated pool or hot tub, relax in the outdoor dining area and enjoy expansive views of the Catskills and the Esopus. 

Modern Meets Rustic Getaway, Hudson, NY 

This stunning home boasts a modern design, minimalist aesthetic, and all designer amenities in a secluded setting so you really feel like you’re getting away from it all. Surrounded by floor-to-ceiling glass windows with views of mountains and your own secluded valley. You’ll have plenty of places to relax, whether you prefer a comfy bed, lounging in the living room, or hanging out in the pool or the hot tub. Features all the amenities, including radiant floor heating, savant smart home system, and automated lighting and shades, and speakers in every room and outdoors. 

Sustainable Modern Tree House, Woodstock, NY 

This winner of the 2009 American Institute of Architects Design Award is very unique, very modern, and very green. Situated thirty feet off the ground, with floor-to-ceiling glass windows give the impression of living in a treehouse. The home is Net Zero, built with sustainable systems including solar panels and a geothermal heat pump for heating and hot water. The house sits on seven secluded acres and features a heated saltwater pool, fire pit, and a 7-foot wood-fired outdoor cedar hot tub. Enjoy outdoor living with over 1000 feet of decking and a screened-in solarium perfect for outdoor dining.