House vacation rentals in Denning

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Top-rated house rentals in Denning

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favourite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock
4.94 out of 5 average rating, 363 reviews

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.

Guest favourite
The entrance of the cottage is framed by lush greenery and vibrant foliage. A stone pathway leads to a welcoming front door, accentuated by an overhanging roof and outdoor lighting. The architectural details are complemented by the surrounding natural landscape.
Home in Kerhonkson
4.99 out of 5 average rating, 308 reviews

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.

Top guest favourite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg
4.99 out of 5 average rating, 106 reviews

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.

Top guest favourite
A cozy outdoor seating area is surrounded by trees and fallen leaves. Four red chairs are positioned around a wooden table, with a fire pit in the center. String lights are draped overhead, creating a warm ambiance in the natural setting.
Home in Livingston Manor
4.94 out of 5 average rating, 163 reviews

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.

Guest favourite
A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.
Home in Hunter
4.95 out of 5 average rating, 187 reviews

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!

Top guest favourite
A modern two-story home is situated amidst lush greenery. The house features large windows that reflect surrounding trees and the sky. A wraparound deck provides outdoor space, complemented by a stairway leading to the entrance. The exterior is painted in a calming grey shade.
Home in Claryville
4.93 out of 5 average rating, 130 reviews

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 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 .

Guest favourite
Home in Grahamsville
4.9 out of 5 average rating, 109 reviews

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.

Guest favourite
A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.
Home in Livingston Manor
4.96 out of 5 average rating, 390 reviews

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.

Top guest favourite
A charming Swiss chalet is nestled among tall trees, surrounded by lush greenery. The house features a welcoming deck and multiple windows that provide natural light. A stone path leads to the entrance, inviting guests to explore the tranquil outdoor setting.
Home in Big Indian
4.99 out of 5 average rating, 138 reviews

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.

Guest favourite
A two-story farmhouse is surrounded by colorful wildflowers and lush greenery. A wide porch features rocking chairs and bright seating areas. The building is topped with a metal roof and a stone chimney, providing a scenic view against a clear blue sky.
Home in Napanoch
4.95 out of 5 average rating, 109 reviews

Cozy farmhouse & stunning views on 135 acres

A gorgeous, spacious and secluded retreat with a fabulous swimming/skating pond and two wood-burning stoves surrounded by 135 acres of meadow and hiking trails, and a short jaunt to miles of untouched wilderness. This 160-year-old farmhouse is super cozy in winter and can easily accommodate large groups but offers plenty of privacy. The place has it all but don't take our word for it - read the reviews and check out the pictures!

Top guest favourite
The exterior of the retreat is illuminated at dusk, highlighting its distinctive architecture with large windows and a welcoming porch. The rustic screen house features string lights, creating a warm ambiance against the backdrop of surrounding trees.
Home in Claryville
4.99 out of 5 average rating, 129 reviews

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.

Top guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances, including a gas stove and refrigerator. A black island is enhanced by a minimalist pendant light above, while natural light floods in through large windows, illuminating a simple green plant centerpiece.
Home in Kerhonkson
4.97 out of 5 average rating, 179 reviews

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

When is the best time to visit Denning?

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Avg. price$385 CAD$375 CAD$356 CAD$364 CAD$386 CAD$375 CAD$414 CAD$432 CAD$358 CAD$358 CAD$394 CAD$414 CAD
Avg. temp-4 °C-2 °C2 °C9 °C14 °C19 °C22 °C21 °C17 °C10 °C5 °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 $180 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Denning vacation rentals include wifi 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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