Best Middletown Hotels

Located in Fleischmanns, River Run Bed and Breakfast is within a 10-minute drive of Belleayre Mountain Ski Center and Belleayre Beach at Pine Hill Lake. This bed & breakfast is 6.9 mi (11.2 km) from Catskill Mountains. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and a fireplace in the lobby. A complimentary breakfast is included. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 9 individually decorated guestrooms. Complimentary wireless internet access is available to keep you connected.

With a stay at Margaretville Motel in Margaretville, you'll be just steps from Catskill State Park and East Branch Delaware River. This motel is 12.3 mi (19.7 km) from Catskill Mountains and 1 mi (1.7 km) from Delaware & Ulster Railroad. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. Free self parking is available onsite. Make yourself at home in one of the 10 air-conditioned guestrooms. Complimentary wireless internet access is available to keep you connected. Bathrooms with showers are provided.

With a stay at Suites on Main in Margaretville, you'll be just steps from East Branch Delaware River and Catskill State Park. This apartment is 13 mi (20.9 km) from Catskill Mountains and 1.8 mi (2.8 km) from Delaware & Ulster Railroad. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. Free self parking is available onsite. Make yourself at home in one of the 5 air-conditioned rooms featuring kitchens with refrigerators and stovetops. Complimentary wireless internet access is available to keep you connected. Conveniences include microwaves and coffee/tea makers, and housekeeping is provided on request.

Located in Margaretville, Margaretville Mtn Inn B&B and Village Suites is in the mountains, within a 10-minute drive of Catskill State Park and East Branch Delaware River. This bed & breakfast is 3.5 mi (5.6 km) from Delaware & Ulster Railroad and 4.5 mi (7.2 km) from Canada Falls. Enjoy recreation amenities such as a hot tub or take in the view from a garden. Additional features at this bed & breakfast include complimentary wireless internet access, concierge services, and wedding services. A complimentary full breakfast is served daily from 7:30 AM to 9 AM. Featured amenities include luggage storage and a library. Free self parking is available onsite. Make yourself at home in one of the 8 individually decorated guestrooms. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Conveniences include separate sitting areas and coffee/tea makers.

Located in Fleischmanns, Shadowcrest is in a regional park, a 5-minute drive from Belleayre Mountain Ski Center and 6 minutes from Pine Hill Community Center. This guesthouse is 4.2 mi (6.8 km) from Belleayre Beach at Pine Hill Lake and 6 mi (9.7 km) from Esopus Creek. Take in the views from a terrace and a garden and make use of amenities such as concierge services. Additional features at this guesthouse include a communal living room, a picnic area, and barbecue grills. A complimentary continental breakfast is served daily from 6:00 AM to 11:00 AM. Free self parking is available onsite. Make yourself at home in one of the 3 air-conditioned rooms featuring Smart televisions. Your bed comes with down comforters and premium bedding. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Private bathrooms with showers feature rainfall showerheads and complimentary toiletries.

Slow Down & Soak Up Summer at Sunday Hollow Welcome to your cozy Catskills A-frame tucked away on 3.5 private acres. With a peaceful mountain stream and a swimmable pond, Sunday Hollow is the perfect spot to unplug, relax, and recharge. Whether you're here for a romantic weekend or a solo nature retreat, this tiny-but-mighty home offers charm, comfort, and seclusion. Located just 15 minutes from Margaretville, Roxbury, Andes, and Bovina, Sunday Hollow is close to town, yet feels miles away from it all. It’s also dog-friendly with prior approval and a pet fee—we’re happy to welcome one well-behaved pup! At 412 square feet, the home is small but thoughtfully designed with vintage finds, soft textures, and big Catskills vibes. The space is warm, welcoming, and full of character—perfect for a couple or a solo traveler looking to unwind. The Layout Enter through a well-stocked kitchen with everything you need to prep meals (note: no microwave or dishwasher). The adjoining living space includes a plush sofa, dining table, and views of the surrounding woods. A wood stove adds warmth and charm in cooler months. The bathroom is simple and functional, with a shower, toilet, and sink. The main floor bedroom features a cozy full-size bed with soft linens. For guests willing to climb, the loft bedroom offers a queen bed and treetop views—perfect for sleeping under the stars. Guests must be comfortable using a ladder to access the loft. Outdoor Living Step out onto the back deck for al fresco dining, charcoal grilling, or simply lounging with a view of the pond. A fire pit, hammock, and walking path through the woods create the perfect setting for stargazing or slow summer mornings. The stream-fed pond is swimmable and a guest favorite. It’s not chemically treated, but it’s wonderfully refreshing on hot days. Before You Book – What to Know We want your stay to be smooth, relaxing, and enjoyable. Please take a moment to review the following important notes before booking: Quiet Hours & Neighbor Respect We love our neighbors—and we know you will too! Please keep outdoor noise to a minimum after 9 PM, especially around the fire pit or deck. Let’s help preserve the peacefulness that makes this community so special. Check-In & Support Check-in: After 4 PM Check-out: By 11 AM Early or late check-in may be available for an added fee with at least 24 hours’ notice. Same-day requests cannot be guaranteed due to cleaning schedules. We’re available by phone or email if anything arises. This is a private home—not a hotel—so response times may vary slightly, but we’ll do our best to assist you promptly. Important Travel Info There is no cell service at the house. Please enable WiFi calling on your phone before arrival so you can make and receive calls over the internet. We recommend saving or writing down key check-in details—such as the address, door code, WiFi info, and host contact numbers—in case you lose signal while traveling. A vehicle is required to get around. There are no ride-share services (Uber/Lyft) or reliable taxis in this rural area. Winter Travel Advisory (October–April) Delaware County is mountainous and beautiful—especially in the winter—but snow and ice are common. Please plan accordingly. We strongly recommend: AWD, FWD, or 4WD vehicles Winter or all-season tires with solid tread Avoiding 2WD or RWD vehicles in snowy or icy conditions The driveway is plowed and maintained in the winter. A shovel is provided to help you clear walkways if needed. Country Living Note This home is located in a rural, natural area. While the exterior is professionally treated, insects or mice may occasionally find their way inside—especially in cooler months when they seek warmth. If you are especially sensitive to wildlife or critters, this may not be the best fit for your stay. Water & Septic System The home uses a private well and septic system, which is typical for this area. Please help us care for it by: Conserving water during dry spells Avoiding water games (sprinklers, kiddie pools, Slip ‘N Slides) Only flushing toilet paper—no wipes, paper towels, or hygiene products Misuse can lead to water shortages or costly repairs, and we appreciate your care and consideration. Land Use To maintain the safety, quiet, and natural beauty of the area, the following activities are not permitted on the property: ATVs Snowmobiles Fireworks Hunting Thank you for your understanding and cooperation. Cancel 60+ days before check-in for a 95% refund Cancellations made within 60 days of check-in are non-refundable All payments are securely processed via Stripe, a trusted third-party provider. Proudly Managed by the property manager This property is proudly managed by the property manager, offering a curated selection of exceptional vacation rentals throughout the Catskill Mountains—from charming village homes to serene mountaintop retreats. Whether you’re planning a weekend escape or an extended stay, we have the perfect space for you to unwind and explore. Your host is also a licensed real estate salesperson with Keller Williams Upstate NY Properties, the region’s most trusted name in Catskills real estate. If you’re thinking about buying or selling—locally or anywhere in the world—feel free to reach out. My business is built on referrals from happy guests, and I’m part of a global network of real estate professionals ready to help you wherever life takes you. A FEW RULES. Check-In and Check-Out: Plan your travel on our listed 4PM arrival and 11AM departure times. Changes in times may be available for an additional fee if possible. Please give at least 24 hours notice for requests, last minute requests may not be possible as cleaning and service schedules are planned in advance. We have awesome neighbors; help keep us awesome neighbors too. - No parties. Only the number of guests on the reservation should be in the house. Let Host know of daytime guests. - No smoking or vaping indoors. If you must smoke, do so outdoors only and extinguish when done then put in the garbage. There will be a $500 fine for evidence of smoking inside the home. - One dog is considered, with approval and additional fee. - No ATV's, snowmobiles, fireworks or firearms. - Quiet hours 9PM to 8AM, keep outdoor noise to a minimum. Cool? Cool.

With a stay at The Wheelhouse Inn in Pine Hill, you'll be in a state park, within a 10-minute drive of Catskill Mountains and Catskill State Park. This hotel is 0.1 mi (0.1 km) from Pine Hill Community Center and 0.8 mi (1.3 km) from Belleayre Beach at Pine Hill Lake. This hotel offers complimentary parking nearby. Featured amenities include express check-in and express check-out. Free self parking is available onsite. Make yourself at home in one of the 7 guestrooms. Complimentary wireless internet access is available to keep you connected. Bathrooms have bathtubs or showers and complimentary toiletries.

With a stay at Starlite Motel in Big Indian, you'll be in a regional park, within a 5-minute drive of Catskill Mountains and Catskill State Park. This aparthotel is 0.9 mi (1.4 km) from Belleayre Beach at Pine Hill Lake and 1.2 mi (2 km) from Pine Hill Community Center. Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. This aparthotel also features tour/ticket assistance, a picnic area, and barbecue grills. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 8 air-conditioned rooms featuring kitchens with full-sized refrigerators/freezers and microwaves. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include coffee/tea makers and irons/ironing boards.

With a stay at Eastwind Oliverea Valley in Big Indian, you'll be in a state park, within a 10-minute drive of Catskill Mountains and Catskill State Park. This hotel is 1.4 mi (2.3 km) from Esopus Creek and 5.3 mi (8.6 km) from Giant Ledge Trailhead. Take in the views from a terrace and make use of amenities such as complimentary wireless internet access and concierge services. Enjoy a satisfying meal at Dandelion Restaurant serving guests of Eastwind Oliverea Valley. Continental breakfasts are available daily from 8:00 AM to 10:30 AM for a fee. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 27 individually decorated guestrooms. Rooms have private balconies. Complimentary wireless internet access is available to keep you connected. Bathrooms feature showers with rainfall showerheads and hair dryers.

With a stay at Urban Cowboy Lodge in Big Indian, you'll be on a river, within a 10-minute drive of Catskill Mountains and Catskill State Park. This luxury lodge is 0.1 mi (0.2 km) from Esopus Creek and 3.9 mi (6.3 km) from Giant Ledge Trailhead. Pamper yourself with onsite massages or enjoy recreation amenities such as a sauna. This lodge also features complimentary wireless internet access, an arcade/game room, and gift shops/newsstands. You can enjoy a meal at the restaurant serving the guests of Urban Cowboy Lodge, or stop in at the snack bar/deli. Quench your thirst with your favorite drink at the bar/lounge. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 28 air-conditioned rooms featuring minibars. Your memory foam bed comes with down comforters and premium bedding. Complimentary wireless internet access is available to keep you connected. Private bathrooms have hair dryers and bathrobes.