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 Loch Sheldrake

4.96 out of 5 average rating, 27 reviews

Magical Catskills Guesthouse. Pool & private lake!

One-of-a-kind magic in the Catskills at “Casa del Monte” — a secluded, luxuriously appointed living space on 10 manicured acres of private land and water. Lake swimming, kayaking, paddleboarding and fishing on property! 5-minute walk from Loch Sheldrake lake and 15-25 minutes’ drive from the area's finest hiking, F&B, and entertainment — including Livingston Manor, Mountaindale, Callicoon, Roscoe, Beaverkill River, Willowemoc, Napanoch, White Lake, and Bethel Woods. 45 minutes from Woodstock.

Guest favorite

Guesthouse in Smallwood

5 out of 5 average rating, 18 reviews

Charming Brook Side Retreat by The Forest Reserve

Kick back and relax in this spacious, renovated XL studio in Smallwood, NY. Located by the tranquil bubbling Brook and surrounded by the Smallwood Forest Reserve, this guesthouse blends modern, vintage, and rustic decor, featuring a comfortable King-size bed. Just 93 miles from NYC, it’s minutes from Bethel Woods Center for the Arts, scenic lakeside dining, lake beaches, and hiking trails. As a Superhost, I’m thrilled to welcome you to my cozy retreat for a peaceful and memorable getaway!

Guest favorite

Guesthouse in Parksville

4.94 out of 5 average rating, 33 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.

Superhost

Guesthouse in Bloomingburg

4.74 out of 5 average rating, 19 reviews

Mondrian Manor

Welcome to the Mondrian Manor in the lower Catskill mountains. This stylish, quiet getaway is a freestanding cottage that includes a private deck and a separate bedroom. Just one hour and forty-five minutes from New York City it has access to many hiking trails, Sam's Point/Ice Caves, Blue Cliff Monastery, unique eateries, and concert venues including Bethel Woods. With a comfortable workspace it will be great for someone needing to finish a project or anyone wanting a peaceful respite.

Top guest favorite

Guesthouse in Narrowsburg

4.99 out of 5 average rating, 132 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.

Superhost

Guesthouse in Hurleyville

4.77 out of 5 average rating, 56 reviews

The Zen Farmhouse - Glamping in the Emerald Forest

The "PEA POD in the Emerald Forest" is located in the woods at The Zen Farmhouse, a historic 1878 farm in the CATSKILLS MOUNTAINS. The area has many charming historic villages within a 30 - 45 minute radius. Hurleyville is the closest, and has been revitalized with many wonderful amenities - the Tango Restaurants - La Salumina - Gallery 222 - Fiber Arts - The Yoga Space - the Hurleyville Performing Arts Center and 8+ mile trail on a wide paved trail along a beautiful marsh.

Guest favorite

Guesthouse in Callicoon Center

4.98 out of 5 average rating, 53 reviews

Beautiful Mtn Cozy Cabin-183 acres-30% off Spring

Truly beautiful mountain cabin. Artistic, eclectic, luxurious—super hi-speed internet—private patio & picnic table—comfy beds, bathrooms with 2 person deep Jacuzzi tubs—house-wide stereo—induction cooking–air-fryer/oven—dishwasher— linens–snacks and drinks included. Geothermal heat/hot water, solar electric — EV charging. Private chef and masseuse available. Farm-to-table restaurants, skiing, hiking, bike rentals, tons of trails, fishing and 183 acres to explore!

Top guest favorite

Guesthouse in Roscoe

4.97 out of 5 average rating, 31 reviews

Private River Access, Beaverkill

Escape to our riverside retreat in the Catskills! This private, detached home offers 2 bdrms, 4 twin beds, and a queen futon. Enjoy exclusive access to Beaver Kill River and a stocked pond with kid-friendly fishing. WiFi, TV, full kitchen, and board games provide comfort and entertainment. Relax on the new deck overlooking the river or gather around the firepit with beautiful chairs. Just 15min from downtown Roscoe's dining, bars, and breweries. Unplug and unwind.

Top guest favorite

Guesthouse in Callicoon

5 out of 5 average rating, 73 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 one small child. Efficiency kitchen (no oven). Ten acres with a creek and lots of area to walk and have a dog. King bed sleeping loft! Great area to explore in summer and winter! Dogs welcome!

Top guest favorite

Guesthouse in Ellenville

5 out of 5 average rating, 17 reviews

The Loft at Pangri-La

Get back to nature in comfort in a newly built loft atop a barn garage with views of the Shawangunk Mountain range. Watch the sunrise over the mountains with a hot cup of coffee while relaxing on the large deck, overlooking the organic garden, beehive, and happy chickens foraging around this 5-acre private property. Owners are next door and available if anything needs attention.

Superhost

Guesthouse in Jeffersonville

4.87 out of 5 average rating, 63 reviews

Enchanting loft & outdoor kitchen on 20 acres

Private, tranquil loft set in the middle of 20 acres. Host lives on property but is quiet and helpful. Local market is 5 mins away. Beautiful lush setting. Easy access to a swimming pond and vegetable garden. Short hikes on property, complete with mushroom and berry foraging. *pond is currently experiencing an algae bloom but there is a beautiful lake nearby for swimming.

Top guest favorite

Guesthouse in Mongaup Valley

4.96 out of 5 average rating, 291 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!!