Vacation rentals in Handsome Hollow

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Top-rated vacation rentals in Handsome Hollow

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Guest favorite

Home in Downsville

4.97 out of 5 average rating, 110 reviews

Trout fishing on the Delaware

Beautiful Private area 2 homes on 10 acres, you will have one, newly built with all amenities, on the river, great fishing, luxurious accommodations, fire stove, local town full size pool with full access, pond / beach with boating, local Knack/ Canoe rental on the East branch of the Delaware River all within 20 minuets. Local antique shops, fairs and markets, Enjoy the Catskills Today. The property boarders the River Just a walk Away. Great for Family and Children. Local food, Shopping and fun

Sep 29 – Oct 6

G$31,604 GYD per night

Guest favorite

Cabin in Downsville

4.86 out of 5 average rating, 134 reviews

Tiny glamping cabin with mineral spring hot tub

This off grid, alternative powered site is located towards the front of a large twelve acre estate, alongside a flowing brook. Elevated over a natural spring that flows year round, the Japanese inspired aesthetics of this private, tiny cabin sits perched atop a deck among the wooded trees overlooking the waterway the mineral spring feeds, but not before filling the in-ground, cedar lined, two person, bubbling hot tub heated with a wood burning stove. One of two glamping sites on the 12 acres.

Nov 25 – Dec 2

G$32,353 GYD per night

Guest favorite

Cottage in Narrowsburg

4.99 out of 5 average rating, 145 reviews

Cozy Cottage in Popular Narrowsburg

A sweet cottage in the artsy hamlet of Narrowsburg welcomes you for a quiet retreat in the country. Moments from the Delaware River and the village, spend hours taking in the serenity of the river and rolling hills of the surrounding countryside, or popping into town for arts and entertainment. There are two separate bedrooms, one with a queen bed and one with a full bed; a well-equipped kitchen; WiFi; a front and back porch; and a deck Come enjoy the all-season splendor of Sullivan County

May 30 – Jun 6

G$27,046 GYD per night

Guest favorite

Guesthouse in Roscoe

4.93 out of 5 average rating, 210 reviews

Comfortable Carriage House Setting in Roscoe, NY

This enchanting carriage house is tucked away a mere five minute drive from the Beaverkill River and about 10 minutes from the hub of the town of Roscoe. Guests have access to the upper dwelling of the carriage house that shares acreage with the main house. Guests can walk the land and explore nature. There is a garden with seating nearby, a pond, a stream running through the property, and a fire pit that guests can enjoy. Perfect get-away spot for a couple that wants to explore the area.

Sep 16 – 23

G$27,777 GYD per night

Guest favorite

Home in Deposit

4.97 out of 5 average rating, 115 reviews

Deposit country home with amazing views

Enjoy a true nature retreat when you visit your getaway home in rural Deposit NY. Located 6 miles off Route 17 at the top of the catskill mountains this property is known for the endless views from sunrise to sunset. The outdoor options are many, whether you're picking fresh vegetables from the home grown seasonal garden or setting up the stone fire pit for s'mores, you'll find there is something for everyone. Great area Fishing, bird watching, and view of the stars. Pets are welcome.

Sep 23 – 30

G$28,953 GYD per night

Guest favorite

Home in Narrowsburg

4.94 out of 5 average rating, 160 reviews

Modern Getaway in the Catskills

Our summer rental has a private entrance adjacent to the main house with kitchen, living & dining rooms, 1 bedroom w/ Queen bed , AC and 1.5 baths. A porch w/ patio furn. a charcoal BBQ and 50 wooded acres to explore. We supply sheets, towels, kitchenware, coffeemaker and 2 flat screen satellite TVs, Internet and WiFi. A great get-a-way for 2 adults. 20 min. to Bethel Woods 30 mins to Resorts World Casino. No smoking, pets or animals or children. All are welcome. Rainbow Friendly.

Jan 18 – 25

G$18,204 GYD per night

Guest favorite

Tent in Livingston Manor

4.97 out of 5 average rating, 110 reviews

Milkweed Camp - Glamping in the Catskills

Our off-grid canvas tent is situated at the edge of a meadow, surrounded by blueberry bushes. It's just 4.5 miles to Main St in Livingston Manor, and 35 minutes to Bethel Woods. Please note that temps may dip below 32F in October. We provide a full-size bed (w/ heated mattress pad), fire pit, firewood, propane heater, and solar power. You have access to a composting toilet & outdoor shower on-site, and a conventional shared bathroom if you preferred. We are an LGBTQ+ inclusive space.

Aug 27 – Sep 3

G$22,644 GYD per night

Guest favorite

Home in Roscoe

4.98 out of 5 average rating, 64 reviews

Lexie by Summer | Modern Rustic Tiny Home

Enjoy this tiny home nestled among five acres of Catskills Forest on a two home lot, just a short distance from essential Catskills towns like Roscoe and Callicoon. The house is a newly built modern studio with a sleeping loft, kitchen, bathroom, wood stove, and large sundeck. It has a separate driveway from the second house on the lot, to maximize privacy for you and your group. Enjoy the wifi, luxury furnishings, thoughtful amenities, and Smart TV in our retreat from the city!

Apr 3 – 10

G$43,696 GYD per night

Superhost

Cabin in Roscoe

4.89 out of 5 average rating, 203 reviews

Getaway Western Catskills - Western Catskills

An easy drive from the city, Getaway is a new way to experience the great outdoors. Nestled across dozens of acres of private woodlands, our modern, tiny cabins have everything you need (comfy bed, bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you relax, unwind and disconnect from the everyday. Plus, as part of your stay, you'll receive firewood, a s'mores kit, coffee and bottled water*.

Apr 18 – 25

G$72,016 GYD per night

Superhost

Home in Long Eddy

4.78 out of 5 average rating, 63 reviews

Bird Spring Hill House - Charming Country Getaway!

This sunny studio apartment surrounded by woods and farmland is perfect for your country getaway. The newly renovated space has modern amenities, farmhouse charm and a deck with a lovely view. Nestled on a quiet road in the hamlet of Long Eddy, there's lots to explore-- tubing & fishing in the Delaware River, hiking trails, swimming in nearby lakes, horseback riding, Callicoon's restaurants & farmer's market, tastings at the local distillery and so much more!

Mar 15 – 22

G$21,352 GYD per night

Guest favorite

Farm stay in Callicoon

4.96 out of 5 average rating, 189 reviews

Country road please take me home!!

Are you looking for rest & relaxation or fun in the Catskills. Come enjoy our warm, cozy home away from home. Our guest mobile home is located on a quiet country back road, but yet close to dining and outdoor activities that the Catskills has to offer, rafting down the Delaware & enjoying concerts at Bethelwoods. The possibilities are endless. We now have Spectrum internet. Please note that we do reside on an active farm. This could be a wonderful experience!

Jan 27 – Feb 3

G$18,944 GYD per night

Guest favorite

Farm stay in Roscoe

4.99 out of 5 average rating, 128 reviews

Roscoe Wildlife Retreat

We are open for. the season! You'll be enjoying a 40-foot travel trailer located on 11 acres of land with private entrance and all necessities to be comfortable, including WIFI, heat/AC, hot water, bathroom.FRESH AIR, and so much more. Please note that the trailer is designed for 2 adults/2 children or up to 3 adults/1 child. If you have a special arrangement for your family, just message us, and we will see what we can do.

Nov 15 – 22

G$24,373 GYD per night