
House vacation rentals in Denning
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Top-rated house rentals in Denning
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Modern Catskills Tiny House Near Hiking Trails
A modern and well- designed home located in the Neversink area of the Catskills. 3 night minimum. The Tiny House has been updated with high-speed 500 Mbps wifi and a separate landline. There is no cell phone service in the immediate area. The house is a short drive to some of the best hiking trails in the area. Enjoy walks in the woods, country drives, or relax on the deck overlooking the pond. 3- night minimum stay. We require our guests to be 24 and over. Maximum of 2 adults. No pets .
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.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Stunning Passive Solar Cabin on 135 acres & pond
Just the perfect cabin. This newly built, passive solar house has a wood-burning stove, incredible views and is drenched with light. The house is intimate yet connected to the outside, with total seclusion and every imaginable modern convenience! It’s an architect-designed marvel of concrete, glass and reclaimed wood that sits on 135 acres of field and forest with a lovely swimming pond and miles of hiking trails. The cabin sleeps up to 6 people in two bedrooms and a spacious sleeping loft.

Parkston Schoolhouse
Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

Mt. Wonder: Cozy Cabin w/ Hot Tub and Wow View
Welcome to the Wonder of the Catskills. With a wood burning hot tub, this secluded cabin sits on 18 acres with creek access, a vast forest & the greatest view in the county. Just 10 min to Woodstock. Seeking a vacation w friends or a romantic escape? Enjoy this rustic 2BD 1ba cabin year-round, incl the natural hot tub & an overall magical feel. Amenities galore incl the tub, BBQ, firepit, wood stove & stocked kitchen. Peruse our books, vibe in nature or enjoy hikes & cute towns nearby.

Modern Riverside Retreat with Firepit, Hot tub
Come enjoythe oasis on the pristine headwaters of the Neversink River with huge backyard, river access, and great kitchen amenities. Offers four bedrooms, and two large baths with bright, sunny living areas. You won't be roughing it! We have a large outdoor stone firepit surrounded by Adirondack chairs, a hot tub, quiet trails for private walks, and all the nature you love. There are three outdoor seating areas for meals and relaxation, a woodstove, and a picture perfect kitchen.

Spacious Catskills Farmhouse on over 5 acres!
Come enjoy some winter fun in the Catskill Mountains! Take the kids skiing, snowboarding, or snow tubing. Warm up with some hot cocoa around the firepit or enjoy a winter BBQ on the deck. Try your luck at the casino or spend a day at the indoor water park. There is snow much fun to be had! You will feel right at home in this charming & restored 5BR farmhouse. Located on 5+ acres near the great Catskills Forest Preserve, this is a great place for four-season recreation.

Creekside Couple's Retreat w/Hot tub, Sauna & More
Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

Modern creekside cabin in the Catskills
Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

10 Min from Bellayre! Gingerbread House!
Perched high among the trees, Gingerbread is a 1950’s Swiss chalet that sits on 4 acres. This is the house everyone slows down for, points and says ‘ that’s the house I would want Upstate’. Well ….she's taken. But I am so happy to welcome you as guests for a short period of time. Gingerbread comes with all the little touches making it feel like the perfect home away for a week, weekend or however long you can escape your regular life.

The Blue House on the Hill Catskills
Spectacular Mountain & Valley Views—Streamside. A beautifully renovated getaway located in the heart of the Catskill Mountains. Upon entering this gorgeous retreat, you will be instantly taken by the designer's attention to detail. Enjoy the open floor plan kitchen with soapstone countertops overlooking the amazing vaulted great room with spectacular views of the farm, valley, and surrounding mountains.
Popular amenities for Denning house rentals
House rentals with a pool

Woodstock Family Home w/ Tree House + Heated Pool

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

Scenic River View Escape | New Paltz

Highwoods Haven | saltwater pool and hot tub

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

Hawk View

Woodstock Getaway - Heated Pool/Hot Tub/FirePit
Weekly house rentals

Sunset Mountain View Retreat · 11 min to Woodstock

West Wing - a unique private space w/deck

Cozy renovated One Room Schoolhouse

Beaver Lake Escape

This New House

Cottage on the Creek

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Sanctuary by the Stream- 20% discount this March!
Private house rentals

Scott Brook Cabin

Blue Quill Cabin on the River

The Stone House

Midcentury House in the Catskills

That 70s Camp

Catskill Mountains Forest Nest for 2

Accord River House

Cozy Cabin • Forest Views • Perfect Winter Escape
When is the best time to visit Denning?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$58,070 GYD | G$56,607 GYD | G$53,683 GYD | G$54,936 GYD | G$58,278 GYD | G$56,607 GYD | G$62,456 GYD | G$65,172 GYD | G$54,101 GYD | G$52,639 GYD | G$59,532 GYD | G$62,665 GYD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Quick stats about house rentals in Denning

Total vacation rentals
Explore 40 vacation rentals in Denning

Nightly prices starting at
Denning vacation rentals start at G$27,155 GYD per night before taxes and fees

Verified guest reviews
Over 2,480 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Denning vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Denning rentals

4.9 Average rating
Denning stays are highly rated by guests—averaging 4.9 out of 5!
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