Guesthouse vacation rentals in Sullivan County

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Top-rated guesthouse rentals in Sullivan County

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

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Guest favorite

Guesthouse in Roscoe

4.93 out of 5 average rating, 209 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.

Aug 11 – 18

G$28,891 GYD per night

Guest favorite

Guesthouse in Parksville

4.88 out of 5 average rating, 16 reviews

Wonderful getaway place in the Catskills!

Enjoy this nice getaway cozy place with your friends and family with a private deck on a beautiful property hosted by a mother-daughter team! Just under 2 hours from New York City! This two-bedroom apartment includes a new kitchen, and living/dining room with a sofabed and accordion doors so it can be turned into a third bedroom for a night. There is also a comfy sitting area with a smart TV. This place is a part of a bigger house. Dogs are ok. We have cats in our part of the house.

Jun 27 – Jul 4

G$32,445 GYD per night

Guest favorite

Guesthouse in Narrowsburg

4.99 out of 5 average rating, 110 reviews

Mission:Possible on the Delaware • Catskill Mtns.

Mission: Possible is the perfect Catskills getaway for two. Nestled along one of the most pristine sections of the Upper Delaware River in Narrowsburg, NY, this modernized guesthouse offers comfort in a luxuriously rustic setting. With three large glass walls facing the river, you can see bald eagles soaring, songbirds flying, blue herons stealthily stalking fish, an occasional white egret or two fishing, and deer quietly drinking at river's edge. Only 15 minutes from Bethel Woods.

Mar 6 – 13

G$37,238 GYD per night

Guest favorite

Guesthouse in Roscoe

4.99 out of 5 average rating, 77 reviews

Map Maker's Cabin

All season cozy cabin in a quiet, peaceful woodsy oasis, 15 min from the Delaware River, and close to many of the wedding venues including Callicoon Hills, Seminary Hill and North Branch Inn. Fast wifi for working remotely, writer's retreat, romantic getaway, meditation, yoga, and time in nature. **We have an (inflatable) hot tub which we are filling week to week depending on the weather - we will see how it does over the winter. So far so good, but please check ahead**

Aug 20 – 27

G$26,811 GYD per night

Superhost

Guesthouse in Wurtsboro

4.83 out of 5 average rating, 23 reviews

Hiker’s Haven, a Cozy Cabin above Bashakill Refuge

Wurtsboro is a charming village nestled in the Catskill Mountains, just a 90-minute drive from NYC. Explore the scenic Hiker's Haven, a secluded Log Cabin Loft with a detached studio and stunning views of the Bashakill Wildlife Refuge. The area offers outdoor activities like hiking, fishing, and glider plane flying, as well as quaint downtown shops and galleries. With its natural beauty and small-town charm, Wurtsboro is the perfect retreat from city life.

Nov 2 – 9

G$29,498 GYD per night

Superhost

Guesthouse in Callicoon

Catskills Creekside Entire Guesthouse

Known for its lush natural environment and country design, The Shirley includes the entire guesthouse comprising of 2 separate units, The Studio and The Cottage (two separate contained units), an outdoor Barn, huge south facing garden with direct access to the Creek. The Shirley sits behind the main house in the village of Youngsville. Livingston Manor is a 10 minute drive North and Callicoon/Roscoe/Narrowsburg/Bethelwoods are all a short drive away.

Jun 9 – 16

G$67,823 GYD per night

Guest favorite

Guesthouse in Callicoon

5.0 out of 5 average rating, 35 reviews

R52Creekside one bedroom cottage

NEW Construction! Centrally located to all Sullivan county has to offer! Bethel woods, Livingston Manor, Callicoon and much more close by! Walk to a great little local deli and drive to many close restaurants. Set up for two adults or two adults with two kids. Efficiency kitchen (no oven). Ten acres with a creek and lots of area to walk and have a dog. King bed sleeping loft and sofa bed in living room. Fun in winter and summer. Pets welcome.

Oct 10 – 17

G$33,988 GYD per night

Guest favorite

Guesthouse in Mountain Dale

4.95 out of 5 average rating, 44 reviews

Willow House Cottage

Sunny guesthouse with plenty of privacy in Mountaindale, Sullivan County, 2-hour drive from NYC. 3 bedrooms, open plan living room/kitchen and dining room, barbeque area, etc. Set in spacious yards behind Main House; stone walls and gardens, fish pond and surrounding forests, with a variety of wildlife. Magically quiet. Vegetable, herb + berry gardens. 10-minute walk to lake and canoe. 1 mile from village. Avail. May to early November;

Oct 31 – Nov 7

G$51,150 GYD per night

Guest favorite

Guesthouse in Long Eddy

4.97 out of 5 average rating, 136 reviews

The Grange

The Grange is a fully renovated 1886 building with 800 sq ft apartment on ground floor. It is located on a quiet country road 4 miles from the Delaware River with great swimming, fishing, kayaking, canoeing, tubing nearby. 15 minutes from Callicoon and 23 minutes from Hancock. Private entrance. Access to my vegetable garden and private lawn. It has fully equipped kitchen and bathroom with bathtub and shower.

Sep 12 – 19

G$30,463 GYD per night

Guest favorite

Guesthouse in Monticello

4.8 out of 5 average rating, 5 reviews

Lakeview Cabin

🌲Welcome. Come to “Lakeview Cabin Feels” layback, take it easy at this unique and tranquil getaway. Hang with friends on this huge lakeside view property filled with paths and sitting areas. Get a Lakeview scene every waking morning. Continue to read our easy and fun description in order to know what is expected of you and what to expect of your stay upon your arrival. Thank you for your future booking.

Jan 4 – 11

G$23,951 GYD per night

Guest favorite

Guesthouse in Mongaup Valley

4.96 out of 5 average rating, 242 reviews

Cozy Cottage - Woodstock Scavenger Hunt w/ prize

The cottage is a cozy little space with great amenities. Jam out with the SONOS speaker or watch any channel on DirecTV during the down time. Large back porch and beautiful gardens with a little pond surrounding the home. We also have a Woodstock themed scavenger hunt for any guest who would like to participate! Prize included for anyone who solves all the clues!!

Apr 8 – 15

G$22,422 GYD per night

Superhost

Guesthouse in Greenfield Park

5.0 out of 5 average rating, 3 reviews

Rustic Catskill's Cabin #2

Delightful, cozy and private Rustic Catskill's Cabin #2 has 2 rooms (1 room with queen bed, 1 room with a single bed and bunk bed ), a desk area, utility kitchen and a lovely front porch with picnic table. The cabin has double burners, microwave, mini-frige, utensils, plates and pan/pots for cooking. 2 shared hot-water bathhouses are but steps away.

Oct 1 – 8

G$25,031 GYD per night