Best Callicoon Hotels

Nestled on six acres of serene and untouched Catskills forest, our charming A-frame chalet invites you to relax and unwind surrounded by nature. This tranquil, renovated abode is only a short distance to two of the hottest towns in the Catskills, where you’ll find local breweries, distilleries, shops, art galleries, and some of the best fishing! Enjoy high-speed WiFi, luxury furnishings, thoughtful amenities, and Smart TV in this quiet, picturesque retreat from the city. As you enter the home you will be greeted by a sun-filled, vaulted ceiling great-room where your group will love to gather. No need to leave the chef out of the party, as this open-concept flows from the living, to kitchen, to dining areas. From the living room, walk out to the expansive deck is outfitted with a large dining area and brand-new grill. Ready for bed? Enjoy the 2 spacious bedrooms with luxury linens and Casper mattresses so you get cool, comfortable sleep. Sleeping arrangements: - Bedroom 1: 1 King Bed - Bedroom 2: 1 Queen Bed Key Features: - Open, spacious floor plan for convenient entertaining. - Newly renovated, fully-stocked kitchen with modern, stainless-steel appliances. - Renovated bathrooms featuring a walk in shower. - 2 spacious bedrooms with luxury linens - Multiple outdoor entertainment areas including an expansive deck with an outdoor grill and dining, a covered porch, and a fire pit. Please pay close attention to following the house rules. Non compliance could result in sizable fines. - All guests staying at a Portoro Homes are required to sign (esignature) a rental agreement and complete identity registration. - Age restrictions apply. Reservation holder must be 25 years of age. - No Parties or Events. - Quiet Hours observed, 10:00pm - 8:00am. - 4WD is required to access the property during winter months. - Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Portoro Homes directly. - Known damages incurred during your stay must be reported to the property manager immediately. - Before check in, we will send you detailed directions to ensure a seamless arrival. - Check-in time is 4:00 p.m. Check-out time is 11:00 a.m. - We cannot guarantee early check ins or late checkouts, fee typically applies. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night. - Some homes have cameras for external monitoring only. - Some homes have pools and hot tubs. There is no guard around the water features. - Use at your own risk. - In the State of New York and in Sullivan County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. - This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host. - Animals/Pets -- Dogs Only, Guidelines and Fee* Animals/pets must be disclosed prior to reservation arrival date, maximum of 2 per stay. Only dogs are permitted in “Pet-Friendly” Property listings. Allowed number of dogs will be expressly stated in the listing and a $150.00 fee per animal/pet is required. Animals/pets are not permitted anywhere on the premises unless prior approval is obtained. Any unauthorized animals/pets at the property will result in a $150.00 per day / per animal/pet fee, and may result in your reservation being canceled, and you may be required to vacate from the Property.

Sunday Lodge & Mountain House is a peaceful retreat on 5 acres in the Southern Catskill Mountains. Our home is located about 2-2.5 hours from NYC, and minutes from the charming towns of Roscoe and Livingston Manor.Tucked away on a mountain road, this is the perfect a place to relax and unwind. You can sleep. You can sip. You can cook. You can workout. You can hang. Outside of our doors you can fish. You can hike. You can stargaze. You can play. A place to do everything or nothing at all.About pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 23.About events:No events allowed.

This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.The spaceThe house on this 3-acre property boasts expansive decks with gorgeous views, making it perfect for nature lovers. You’ll feel the serenity as you drive up and down the steep hills toward the property. Walk through the garden to access the North Branch of the Callicoon Creek, which cuts right through the corner of the property, and catch a glimpse of the local wildlife. Snuggle up on the wraparound couch facing the fireplace in the winter as you watch the snow falling quietly around you. In the summertime, stretch out and watch the stars break through the sky on the patio in the front or on one of the 2 decks.A well-equipped eat-in kitchen leads to a lovely screened porch for outside dining. From the large living/family room you enter into the pool enclosure with the in-ground, heated swimming pool. Stretch out and relax on the sunny deck for a truly memorable vacation.This house boasts a rustic wooded entry and a fully stocked kitchen with all updated appliances. There are two wood-burning fireplaces, cathedral ceilings, large windows, recessed lighting, and a propane grill on the screened deck. The property has broad grassy yards, perfect for Frisbee games in the summer, or snowball fights in the winter.From the spacious floor plan to the large private decks and yards, to the beautiful views, this is the perfect home for a relaxing getaway.There are a total of 4 bedrooms, of which 2 of them have 1 king bed, and the 3rd bedroom has 1 full bed, and the 4th bedroom has 2 single beds with one trundle bed that can be pulled out (preferably for kids). There is one half-bath on the first floor and 2 full bathrooms on the second floor (one is an en-suite from the master bedroom).Additional air mattresses can also be provided upon request.About pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Welcome to Modern Manor on Maple!Built in the 1920s, this charming two-story farmhouse is located in the heart of Jeffersonville. It’s conveniently a walking distance to a restaurant, a supermarket, and an local shops. For entertainment, there is the famous Bethel Wood performing Arts Center only 15 minutes away. The town of Callicoon is nearby and the Delaware River for all those nature lovers. Two hour trip from NYC for those looking for a quick getaway. Follow us @maplehillgroup on Facebook/Instagram for more!About pets:Pets allowed: limit 2 total.Any damages found after visit will be charged.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.Kids are allowed but must byo baby amenities.About customRules:All garbage must be thrown out after stay in bins located outside in the driveway..All linens and towels used place in hamper located in second floor bathroom.,All furniture and appliances must be placed back in original areas before leaving. While also making sure all heating/cooling and lights are all off.About checkIn:Flexible check-in available (contact host in advance of arrival).About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

Located in Callicoon Center, Callicoon Hills is within a 15-minute drive of Callicoon Town Hall and Catskill State Park. This hotel is 13.2 mi (21.2 km) from Bethel Woods and 13.5 mi (21.7 km) from Bethel Woods Center For The Arts. Don't miss out on recreational opportunities including a sauna and a 24-hour fitness center. Additional amenities at this hotel include complimentary wireless internet access, an arcade/game room, and a banquet hall. Enjoy a meal at Conover Club or snacks in the coffee shop/cafe. The hotel also offers room service (during limited hours). Quench your thirst with your favorite drink at the bar/lounge. Full breakfasts are served on weekends from 10:00 AM to 1:00 PM for a fee. Featured amenities include a business center, express check-out, and a 24-hour front desk. Free self parking is available onsite. Make yourself at home in one of the 65 guestrooms. Complimentary wireless internet access is available to keep you connected. Bathrooms feature bathtubs or showers, complimentary toiletries, and hair dryers.

Welcome to Winterberry Pond, our completely renovated converted barn which is nestled on 7+ private acres. This two bedroom, one bathroom home has a modern aesthetic, having undergone a comprehensive renovation in 2022, and a brand new hot tub added in 2025. Located just 10 minutes from Roscoe and 15 minutes from Livingston Manor, this spot is the perfect spot to explore all that the area has to offer. As you step through the front doors, you'll be greeted by a wall of windows on your right, flooding the interior with natural light. The expansive open area seamlessly combines the living room and an inviting eat-in kitchen. The bathroom, adorned with beautiful tile work, is a sight to behold. Sunlight bathes the open floor plan throughout the day, creating an ideal environment for conversations while preparing a meal or enjoying a glass of rosé. Vaulted ceilings add to the spacious and airy ambiance, making this an inviting space for all your gatherings. This home comfortably accommodates 4 guests with 2 spacious bedrooms featuring luxury linens. Outside, the home is thoughtfully situated away from the road, offering a sense of seclusion and privacy. The property boasts over 7 acres of land, adorned with mature trees that are just waiting to be explored. The generously sized yard provides ample space for outdoor activities, with the additional the included hot tub to relax & soak up the suds & views! Many a summer afternoon can be enjoyed row boating on the private pond, where the abundant wildlife promises to excite and entertain. Please note that while you are welcome to enjoy the pond, we advise using it with extreme caution as it is swim at your own risk. Sleeping arrangements: Bedroom 1: 1 king bed Bedroom 2: 1 queen bed - Set off the road on 7+ acres of remote Catskills land. - Cozy living area with open floor plan for convenient entertaining. - Fully-stocked kitchen with modern appliances and an island with a breakfast bar. - Modern renovated bathroom featuring a walk in shower. - 2 spacious bedrooms with luxury linens. - Spacious backyard for gathering and entertaining including a fire pit, outdoor dining and grill set-up. - Private pond on the property for row boating and various activities. Please note that while you are welcome to enjoy the pond, we advise using it with extreme caution as it is swim at your own risk,. - Convenient proximity to hiking trails, nature, and ski mountains for year-round outdoor activities - Short drive to the towns of Roscoe and Livingston Manor - INTERNET: The internet at this property is provided by ViaSat a satellite internet company. This can cause the internet to fluctuate and possibly not allow consistent connection. Please pay close attention to following the house rules. Non compliance could result in sizable fines. - All guests staying at a Portoro Homes are required to sign (esignature) a rental agreement and complete identity registration. - Age restrictions apply. Reservation holder must be 25 years of age. - No Parties or Events. - Quiet Hours observed, 10:00pm - 8:00am. - Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Portoro Homes directly. - Known damages incurred during your stay must be reported to the property manager immediately. - Before check in, we will send you detailed directions to ensure a seamless arrival. - Check-in time is 4:00 p.m. Check-out time is 11:00 a.m. - We cannot guarantee early check ins or late checkouts, fee typically applies. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night. - Some homes have cameras for external monitoring only. - Some homes have pools and hot tubs. There is no guard around the water features. - Use at your own risk. - The house is regularly treated for pests but being that we are in the country, it would not be unusual to have an insect or mouse make an appearance inside. - In the State of New York, and in Sullivan County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. - This is a No Pets property. A daily rate fee of $150.00 will apply for violations and you may be asked to vacate the premises with no refund at the discretion of the Host. - This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host. - Private pond on the property for row boating and various activities. Please note that while you are welcome to enjoy the pond, we advise using it with extreme caution as it is swim at your own risk,. - INTERNET: The internet at this property is provided by ViaSat a satellite internet company. This can cause the internet to fluctuate and possibly not allow consistent connection.

With a stay at The North Branch Inn in North Branch, you'll be within a 15-minute drive of Callicoon Town Hall and Villa Roma Driving Range. This inn is 12.9 mi (20.8 km) from Bethel Woods and 13.6 mi (21.9 km) from Bethel Woods Center For The Arts. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and wedding services. This inn also features a fireplace in the lobby, tour/ticket assistance, and a picnic area. At The North Branch Inn, enjoy a satisfying meal at the restaurant. Wrap up your day with a drink at the bar/lounge. A complimentary full breakfast is served daily from 8:00 AM to 10:00 AM. Featured amenities include complimentary wired internet access, multilingual staff, and a library. Free self parking is available onsite. Make yourself at home in one of the 14 individually decorated guestrooms. Your bed comes with down comforters and premium bedding. Complimentary wireless internet access is available to keep you connected. Detached private bathrooms with showers feature designer toiletries and hair dryers.

An old farm with a big beautiful garden that you can stroll through and eat directly from. From the seasonal stream to the hiking trails and back to the heated pool. This house has all the daytime fun. At night, please make a bonfire and roast marshmallows or go for a nighttime swim under the stars. Adult and family camp is here…About pets:Pets allowed: less than 50 lbs per pet (limit 2 pets total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking allowed: in designated areas.About events:No events allowed.

Your cozy getaway awaits in Jeffersonville at this brilliant house. With 4 bedrooms including a king, queen, twin, and futon, this home offers a tremendous space for guests to relax. Enjoy the convenience of 2 bathrooms equipped with a shower, bathtub, and hair dryer. You're sure to make fantastic memories with a stay at our place.About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.