Family-friendly vacation rentals in Zena

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Woodstock Chalet - Peace & Quiet & Space (O my!)

Read the REVIEWS: Feel right at home in our spacious light-filled studio on a private drive (Reserve ahead for your dog.) 4 acres of surrounding forest ensure quiet… windows on 3 sides (plus a stargazer skylight) yet easy access to town and to the local bus. All the comforts of upscale suburbia. Great A/C PLUS Just a 2-minute drive to Woodstock center (galleries, parks & shops) 5 minutes to Levon Helm’s barn and Bearsville (live music.) Yr private woods are a photographers/birdwatchers delight.

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.

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

Woodstock Family Home w/ Tree House + Heated Pool

Town of Woodstock Special Use (aka STR) Permit #23-0683. Featured in Hudson Valley Style Magazine, this fully updated modern farmhouse is ready to host. Radiant-heated full baths, whole-house generator, PRIVATE heated saltwater pool (schedule/weather permitting), four-season porch, indoor fireplace, fully equipped kitchen, outdoor grill, etc. Basement includes ping pong and pool tables. All bedrooms and full baths upstairs. Half bath on the main floor. Dogs are not permitted at any time.

Redbird 1926

A charming one 1 BR apartment attached to our home with a private deck. Entrance to deck and apt. is up eight stairs. Located in a quiet country setting 5 min. from the center of Woodstock and 15 min. from Kingston. This lovely apt. includes central A/C, WiFi, Roku, refrig., outdoor gas grill, microwave, toaster, coffee maker, sink, counter top electric burners, no oven. The bedroom has queen size bed. LR has a day bed for added sleeping space. Come spend time in a tranquil setting.

Woodstock Private Suite: Ensuite Bathroom/Patio

Spacious and flooded with daylight, this spacious room has a comfortable king sized bed and a roomy ensuite bathroom. Two sets of sliding patio doors let in lots of daylight and lead out to your patio space and a backyard. You'll enjoy a picturesque view of trees and wildlife. The suite is situated on the ground/lower level of my home and is a peaceful and comfortable spot to land. It's located on a quiet tree lined residential street 2 1/2 miles away from Woodstock's center.

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

The Carriage House: Studio

We offer a private studio apartment located on the second floor of this wonderfully restored 2 unit carriage house, built in the early roarin' 20's! It offers a blend of modern amenities, with more traditional countryside accents. The traditional design of the studio allows light to pour through the apartment, while making adjustments for sleeping in easy. This truly unique space is a perfect place to take a weekend to relax, and enjoy our exterior grounds!

MCM Oasis | EV | Hot Tub

As featured in Atomic Ranch & Country Home Magazines, the Maverick is a secluded luxuriously restored 1964 MidCentury deck home furnished with Eames and other iconic era furnishings. The Maverick is secluded yet just 5 minutes from downtown Woodstock as well as beautiful hiking, running, and biking trails. The home is perfectly set up for indoor | outdoor entertainment & dining. Be the first to try our new 7 person luxury spa hot tub!

Heated Pool • Private • 4 Min to Woodstock

Welcome to your private Woodstock retreat — a bright four-bedroom home just four minutes from the village. Spend your days by the heated salt-water pool, grill and dine on the expansive 2,000-square-foot deck, or gather around the fire pit beneath the pines. With two fireplaces, multiple living areas, and a large tree-lined garden, the home offers the perfect balance of privacy, comfort, and connection in the heart of the Catskills.

The Woodstock Suite

Welcome to The Woodstock Suite! It’s the perfect retreat for those seeking a peaceful getaway in the heart of nature, just minutes from the center of America's most famous small town—Woodstock, New York. The Suite is located in a lovely residential neighborhood on a quiet tree-lined street. Bright & airy during the day and comfortable & cozy at night, this newly renovated space is designed with your tranquility in mind.