Vacation rentals with a pool in Hudson Valley

Scenic River View Escape | New Paltz

Unwind in nature at this scenic New Paltz escape, located on a serene riverbank with spectacular views. Large porch and private backyard are perfect for relaxation and stargazing. Recently renovated, the house blends modern amenities with a tranquil atmosphere. Thoughtfully designed, it features a cozy fireplace, large smart TV, and fully equipped kitchen. Explore nearby hiking trails, waterfalls, and Minnewaska State Park, or relax in the hot tub. Ideal for couples, families, and remote workers

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

Woodstock Mountain Cottage w/ Pool /Swim

This romantic 2 bed cottage has large beamed ceilings, fully stocked kitchen, bathtub, mountain views, and hiking trails. We use strict cleaning protocols to ensure each stay is perfect and feels like home. The house is equipped with fast wifi and a ROKU Ultra for all of your tv needs! Located just 3 mins driving to the center of Woodstock. Swim in the pool, hike a nearby trail, enjoy nature, grill or relax in the hammock. Pool is shared with hosts. No guests of guests allowed and no parties.

Secluded Kingston Cottage with Heated Pool

Relax into summer at this cozy vintage Catskills retreat with a heated saltwater pool (open late May–September). Just minutes from Kingston, High Falls, and Stone Ridge, with easy access to top restaurants, farmers markets, hiking trails, rail trails, and swimming holes. The home features 2 bedrooms, 1.5 baths, a large private yard, stone patio, fire pit, and BBQ—perfect for couples, families, friends, or peaceful midweek escapes. Pet-friendly with a backup generator on-site for peace of mind.

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.

Mtn View Lux Dome w/ Heated Plunge Pool

This luxury dome is a modern home perched on a mountain top. Our aim is to combine the comforts of a large hotel suite with all the healing qualities of nature. Venture out or hike our own trails leading to a pond and a stream in the woods. Suited for long term WFH stays! We have Fiberoptic internet (ethernet avail) and plenty of space for your setup. Stroll the property at lunch or jump in the heated plunge pool between calls. Ask me about a special offer for long term stays. (14 days +)

Hike & Sauna! Modern Mountain Escape

Welcome to a brand-new custom-built A-frame nestled in the heart of the Catskills. Set in the slopes of Pakatakan Mountain and surrounded by protected forest. Inspired by traditional A-frame designs, every detail has been carefully considered. From the curated home away from home experience to the high-end finishes and modern amenities. Enjoy a wraparound deck overlooking the forest, beautiful stone landscaping, a fire pit, outdoor grill, and plenty of space to relax and unwind outdoors.

Design Scandi Retreat, Heated Pool, Dogs Welcome

Escape to BoHo Farm House, a Japandi-inspired retreat on 8 private acres in Accord, in the Hudson Valley. Spend sunny afternoons beside the pool, grill local finds, and stargaze around the firepit. The screened porch offers the perfect setting for relaxed meals on warm days next to nature. Stroll the property and pick fresh seasonal herbs and veggies from the garden. Featured in PureWow's list of pet-friendly escapes near NYC, BoHo Farm House was designed for effortless year-round living.

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Hudson River Sunset Getaway

With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

At the end of a dead end road on 12 acres, you'll find the perfect retreat. Highlights include a natural swimming pool, yoga deck, outdoor Japanese hot tub and sauna. Chef's kitchen, grill and smoker. Living room has a piano and seats a large group. Outside there's a 3 level stone patio, deck and firepit w/outdoor sound system. Private yoga & in-home massage. Peloton bike, Temperpedic & saatva mattress, beautiful linens! *extra 6 guests w/rental of guest house!

A Lovely Cottage in the Woods (Pool Open!)

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.