Cottage vacation rentals in Olive

Beautiful stream side cottage in the woods

Stunning fully renovated 1970 partial A frame cottage in the woods! Set privately on four acres with a stream and meandering stone walls, the cottage is modern yet rustic, with a mid century decor. Main floor has living room with beautiful floor to ceiling stone fireplace (gas operated), kitchen, bathroom, and an office with a desk and twin bed. Second floor has master bedroom with queen size bed and a separate loft area with desk. Great place to relax in nature - a perfect couple's getaway!

Location · Value · Bathroom

Peaceful Cottage-in Private 5-acre field

Modern cottage with large outdoor living area in a beautifully secluded 5-acre field. A quiet and romantic getaway centrally located to Arrowood Farms, Westward Orchard, Inness Resort & Golf, Butterfields, Ollie's, as well as local hiking including Minnewaska State Park and the Mohonk Mountain House. Escape to a calm and relaxing environment with updated amenities yet pet-friendly. Enjoy lounging and dining on the deck while watching the wildlife or simply roasting s'mores in the fire pit.

Value · Family · Quiet

Apartment Therapy Woodland Cottage • Pets OK

Escape to a private woodland retreat in the heart of the Hudson Valley. Nestled among the trees in Stone Ridge, this cozy cottage blends rustic charm with modern comfort, offering the perfect setting for a romantic getaway, family vacation, or peaceful work-from-home escape. Enjoy your morning coffee surrounded by nature, spend evenings under the stars, and explore nearby Woodstock, Kingston, Mohonk Preserve, Minnewaska, local farm stands, breweries, and some of the region's best hiking trails.

Family · Location · Comfort

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

Location · Value · Decor

Gorgeous Waterfront w/ Hot Tub and Game Level

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to The Glass House! Here are a few things I think you’ll especially enjoy about the house. Highlights – You’ll love the: Peaceful waterfront setting – tucked away on the lake, yet just minutes to town Year-round hot tub – the perfect way to unwind after hiking, or exploring Family-perfect layout – two spacious levels with a game/media room and screened porch Kayaks & life vests – easy, safe access to the water for all ages

Family · Location · Accuracy

Leggett Cottage

The cottage is located in historic High Falls on Leggett Road, one of the loveliest roads in the area. It is your private cottage. Just renovated, it has new amenities. A well-equipped kitchen. The location is 100 steps from the rail trail, where you can bike or walk. Stone Ridge and High Falls are a half-mile away for all your shopping. Situated between the majestic Shawangunks and the Catskills, outdoor activities, farm-to-table restaurants, breweries, and farmers' markets abound.

Value · Family · Grill

“Green Meadow Cottage”, updated 1850’s farmhouse.

Relax with friends or family in this cozy updated 19th century farmhouse cottage set on 5 acres surrounded by pasture and forest. This is truly a rural setting to enjoy the serenity of nature. Centrally located, a leisurely country drive will take you to quaint towns, spectacular hiking, fine dining and more. Visit our many breweries and distilleries or just take a drive and explore. Bring your bikes and ride the gently rolling wooded roads… or not. It’s your vacation.

Value · Family · Parks

Relaxing Cottage in the Catskill Mountains

1000 sq ft. cottage located on a 7 acre partially wooded property in the Catskills. Two bedrooms (one queen, one full), one bath, open floor plan with vaulted ceilings and sliding glass doors opening to a deck in the back yard. Cook and eat on the deck with both gas and charcoal grills, plus large dining table with umbrella. Fire pit outside and wood burning stove inside for extra warmth and ambience. Equipped with a backup generator. Dogs considered, just ask.

Location · Family · Bathroom

Coldbrook Cottage

Welcome to Coldbrook Cottage. Less than 2 miles from The Onteora Mountain House wedding venue. A great romantic get-a-way. All 5-STAR reviews. We offer the amenities of a great hotel suite, but totally private. It's on one of Woodstock's nicest roads for walking, jogging, and bicycling. Wilson State Park is across the street and we're surrounded by protected land. 8 minutes to Woodstock. 20 minutes to Kingston. 20 minutes to skiing . Check our reviews!

Location · Value · Backyard

PerchCottages #11: Creek access + Sauna + Mt views

A group of modern cottages with spectacular mountain views, and magical creek frontage on the Esopus Creek (with its own beach and swimming hole!) Completely renovated. Quick 2 HR drive from the City. ✔ Fishing and Swimming ✔ 1 Dog or Cat per cabin allowed ✔ Gas BBQ Grill ✔ 40” Smart TV ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Onsite parking 7 mins → Ashokan Rail Trail 25 mins → Belleayre Ski Resort

Location · Family · Walkability

Ye Little Wood | Cozy Forest Cottage with Hot Tub

Stay at our comfortable and private 2-bed/2-bath home with covered porch, hot tub, fire pit, outdoor shower, and additional office cabin (perfect for work, exercise, or meditation) all surrounded by beautifully wooded forest. Centrally located in Kerhonkson just 15 minutes from local farm markets, popular farm-to-table restaurants and breweries, and hiking and other outdoor activities.

Family · Location · Decor

Cozy MCM Cottage | Pets Stay Free

Welcome to Cherrytown Cottage, a cozy mid-century modern bungalow tucked into the woods. It’s a comfortable home base for solo travelers, couples, friends, or small families—just minutes from some of the region’s best hiking, restaurants, orchards, and breweries. Spend the day exploring, then come home to play records, light the fireplace, or gather around the outdoor firepit.

Value · Family · Wifi