
House vacation rentals in Denning
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Top-rated house rentals in Denning
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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.

Cook House | Modern Cottage w/ Hot Tub & Fireplace
Featured in Vogue, Curbed, and Remodelista, Cook House is a fully renovated modern cottage in the Catskills with cozy minimalist vibes and kitchen gear designed to inspire your inner chef. Enjoy cooking while records spin across the Sonos. Eat al fresco on the porch, then head to the hot tub. Or binge your favorite show on the projection screen at the foot of the bed. Great for couples or individuals looking to relax and enjoy nature. Hosted by The Reset Club, a member of 1% for the Planet.

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.

Modern House with Mountain View @Getawind
Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Modern Catskills Tiny House Near Hiking Trails
A modern and well- designed home located in the Neversink area of the Catskills. The Tiny House has been updated with high-speed 200 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 .

Spacious Catskills Farmhouse on over 5 acres!
Come enjoy autumn in the Catskill Mountains! Fall is the best time to visit the Catskills! Crisp nights, fresh apple cider, U-pick farms, bonfires, & picture-perfect fall foliage. Get outside and explore our trails, parks, and lakes or visit the local casino or indoor waterpark. 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.

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.

Gingerbread House- a 1950s Catskills Chalet
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.

Special: Rustic Farmhouse with Firepit & Power
Relax with the whole family at this peaceful place to stay. Super private, pet-friendly farmhouse, 2 hours from NYC in Catskills. ✔ Backyard w/ firepit ✔ Dogs allowed** ✔ 400Mbps Wi-Fi ✔ 50” Smart TV ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Back deck w/ BBQ grill ✔ Indoor fireplace ✔ Baseboard heating + Window Acs ✔ Onsite parking 20 mins → Minnewaska State Park 30 mins → Mohonk Preserve

ENTER HOME - Minimalistic style warm & inviting
ENTER our HOME with an inviting comfortable setting filled with natural light and clean lines inspired by Nordic Design. Full new kitchen with all Bosch appliances including washer and dryer. Our home is designed to embrace the beautiful nature around you and to bring peace and comfort to your stay. ENTER HOME is great for individuals, couples, or families with kids. AC in both bedrooms only
Popular amenities for Denning house rentals
House rentals with a pool

Shula | Farmhouse | Pool, Fire pit, Hot tub

Modern Woodstock Retreat w/ Heated Pool & Fire Pit

midcentury mod * HOT TUB * walk out trail 2 mohonk

4Br Mountain Brook House on 130 acres w/ trails

Hawk View

Upstate Modern Scandinavian Barn in the Catskills

Pool Hot tub Sauna Canoe Country Lakehouse

Peace & Privacy - High Falls (hot tub & salt pool)
Weekly house rentals

Scott Brook Cabin

Fall Special: Relax, BBQ, Save, Farmhouse 2hrs NYC

Blue Quill Cabin on the River

The Willowemoc Schoolhouse

Stony Clove Cottage - sleeps 6, *maximum 4 adults*

Charming Cottage on 12 Secluded Acres + Hot Tub

Wooded Livingston Manor Oasis With Stream & Deck

Modern dreamy Hudson Valley home
Private house rentals

Livingston Manor Forest Cottage

Hudson Valley Black Barn w/ Firepit + Fireplace

littleburnthouse in Highmount NY

That 70s Camp

Catskills Architect-designed Modern Cabin retreat

Modern Mountain Oasis * Fire Pit/Grill/Coffee Bar

Stunning Country Contemporary w/ FP & Views

Trail's End - Modern + Private Cabin in the Wood
Quick stats about house rentals in Denning
Total rentals
40 properties
Nightly prices starting at
G$27,186 GYD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Rentals with a washer and dryer Denning
- Family-friendly rentals Denning
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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Zoom Flume
- Brotherhood, America's Oldest Winery
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Windham Mountain
- Villa Roma Ski Resort
- Mount Peter Ski Area
- Plattekill Mountain
- Opus 40
- Hunter Mountain Resort
- Benmarl Winery
- Millbrook Vineyards & Winery
- Ventimiglia Vineyard
- Applewood Winery
- Warwick Valley Winery & Distillery
- Hudson Chatham Winery
- Three Hammers Winery