Holiday rentals with breakfast in Sullivan County

A perfect couples fall getaway

For an unforgettable escape, stay at the Hammer House at Three Hammers Winery, a beautifully restored 1820 historic farmhouse blending classic charm with modern comforts. This inviting retreat features a fully equipped kitchen, spacious living areas, and cozy bedrooms, all complemented by a covered porch overlooking a scenic pond and vineyard, plus a patio with a fire table for relaxing evenings. Its prime location offers easy access to the Pocono Mountains. Relax, Fine Wines, Beautiful scenery!

The River Cottage

Cozy studio cottage on a country road. Loft for extra guest / big kids. Adjacent to Soaring Eagle campground: kayak/tube tours, river access day pass, snacks, supplies. 10 min to Callicoon, NY: restaurants, pubs, groceries, gas, bank, pharmacy, laundromat, shopping, movie theater. 15 min to French Woods Camp 30 min to Bethel Woods (Woodstock Festival site) *EARLY IN / LATE OUT BY REQUEST $25/hr Pay in Resolution Center Please book your stay with the correct number of guests. Thank you!

Summer Escape! Firepit, Lake, Kayak, Pools & Tiki

CASA AURORA: Escape to our eclectic & colorful 3BR/2BA cabin w/firepit in Masthope, an all-season Poconos gem with infinite amenities! Enjoy summer lake days on Masthope beach with free SUP/kayak rentals. Masthope also boasts 2 outdoor pools, Tikibar, grills, horseback riding, zoo, courts, minigolf, gym, skiing & tubing. The updated home features a jetted tub, gas fireplace, gas grill, screened porch, deck & firepit area. Perfect for summer fun or winter adventure—Ski Big Bear is 5 mins away!

Relax by the Pool or on the River! Perfect Break.

A home filled with light and surrounded by nature! Large open spaces inside and out for family and friends to spend quality time together. Set at the top of the hill, backed by its own private patio with fire pit and grill and neighboring our lovely kitchen garden. Our 2,200 square foot guest house features four queen-sized bedrooms, a fifth with two bunk beds and three bathrooms. Relax in the spacious living room or enjoy the bright and airy kitchen and dining room. The perfect get-away!

Neversink Retreat:Luxury 3br 15-acre hobby farm

Pricing on weekdays are lower than weekends; pricing varies. Book 7+ days and save 10%. Escape the city and reconnect with nature at Neversink Retreat - a refined country escape in the heart of the Catskills. Set on 15 private acres, this newly built, custom-designed 3-bedroom home blends modern comforts, privacy, and a peaceful setting easily accessible to from Livingston Manor, Roscoe, and Bethel. Perfect for all-season getaways, it’s where nature, style, and serenity come together.

Cottage near Bethel Woods

Only 20 min from Bethel Woods concert venue and museum. 10 min from rafting the Delaware River. There is so much to do no matter when you plan to make your way over to this special spot. Two bedroom cottage with everything you need for a great escape. Only 2 hours away from the city and 30 min from Port Jervis (the local train station). There are two bedrooms, a fully stocked kitchen and full bathroom plus a fire pit, trampoline, seasonal salt water pool and walks in the woods.

Mahaska Creek

This comfortable 2 bedroom, one bath home is situated along road 164 in the Beechwoods and only 2 miles to downtown Callicoon and the Delaware River! Located along a stream, it boasts a beautiful private back deck,. Spectrum Wi-Fi provides hi-speed internet for weekend entertainment or extended stays working from home. Close to the Villa Roma, Bethel Woods, and the quaint towns of Western Sullivan County, it’s a great place to enjoy life in the Catskills!

The Fern Hill Lodge: Secluded Serenity on 20 Acres

The Fern Hill Lodge is a lovingly restored retreat, crafted by a local master carpenter and designed for families, couples, or friends ready to escape the city and reconnect with nature. Just two hours northwest of NYC, our private, secluded rustic sanctuary is tucked away on a lush, ferntastic hilltop — a hidden gem nestled on 20 peaceful acres. Whether you’re here to explore, rest, or simply breathe, the entire house and land are yours to enjoy.

Stargaze Lodge

The house is brand new. It is set back off the road. its just minutes from the D&H Canal & Neversink river , 15 min from Bashakill vineyards Oakland valley race track, also trains are available in either Port Jervis or Otisville & the same time to rt 17 or 84. 30 minutes to the Monticello casino or rt 97 Barryville also ski locations near both places , 35 minutes to Warwick and Chester legoland & Milford Pa ,Bethel woods, Milford PA.