Callicoon holiday rentals

We found 179 holiday rentals — enter your dates for availability
Discover a selection of 15 homes and other holiday rentals in Callicoon that are perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as a hot tub and garden. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Callicoon

Showing deals for:4 Dec - 11 Dec

Private kitchen
Terrace/patio
Living area
Exterior
Exceptional
(26 reviews)

Entire Catskills Retreat - Hot Tub • Sauna • Fireplace • Vinyl

Jeffersonville

12% off
AU$3,328
for 7 nights, 1 cottage
AU$475 per night
includes taxes & fees
Entire Catskills Retreat - Hot Tub • Sauna • Fireplace • Vinyl
Exterior
Pool
Dining
Exterior detail
Exceptional
(85 reviews)

Private Hilltop Getaway with Hot Tub & Saltwater Heated Pool

Damascus

8% off
AU$5,523
for 7 nights, 1 home
AU$789 per night
includes taxes & fees
Private Hilltop Getaway with Hot Tub & Saltwater Heated Pool
Terrace/patio
Private kitchen
Interior
Property grounds
Exceptional
(5 reviews)

Charming 2-bedroom Country Cottage with Hot Tub

Obernburg

11% off
AU$3,014
for 7 nights, 1 cottage
AU$431 per night
includes taxes & fees
Charming 2-bedroom Country Cottage with Hot Tub
Interior
Terrace/patio
Exterior
Large window in loft for evening star gazing or morning views into the pasture.
Exceptional
(6 reviews)

Milk House @ Indigo Bunting Farm

Callicoon Center

8% off
AU$2,737
for 7 nights, 1 cottage
AU$391 per night
includes taxes & fees
Milk House @ Indigo Bunting Farm
Outdoor dining
Dining
Living area
Interior
Exceptional
(6 reviews)

Dancing Doe Estate with Wood Stove, Hot Tub & Firepit

Jeffersonville

12% off
AU$5,151
for 7 nights, 1 home
AU$736 per night
includes taxes & fees
Dancing Doe Estate with Wood Stove, Hot Tub & Firepit
Property grounds
Exterior
Private kitchen
Room
Exceptional
(10 reviews)

Private 5-Acre Farmhouse Retreat - Bethel Woods 25 mins - Sleeps 8

Livingston Manor

8% off
AU$2,746
for 7 nights, 1 home
AU$392 per night
includes taxes & fees
Private 5-Acre Farmhouse Retreat - Bethel Woods 25 mins - Sleeps 8
Room
Dining table with 8 chairs
Living Room
Outdoor fire pit with comfy chairs
Exceptional
(13 reviews)

Private vollyball court: 5-Acre Haven with AC close to Bethel Woods.

Narrowsburg

11% off
AU$2,642
for 7 nights, 1 home
AU$377 per night
includes taxes & fees
Private vollyball court: 5-Acre Haven with AC close to Bethel Woods.
Interior
Property grounds
Outdoor shower.
Evening ambience.
Exceptional
(40 reviews)

Amenity filled camper with direct Delaware River Access

Equinunk

8% off
AU$1,242
for 7 nights, 1 home
AU$177 per night
includes taxes & fees
Amenity filled camper with direct Delaware River Access
Fitness facility
Outdoor dining
Interior
Private kitchen
Wonderful
(14 reviews)

Breathtaking River Front Cabin

Damascus

12% off
AU$2,887
for 7 nights, 1 home
AU$412 per night
includes taxes & fees
Breathtaking River Front Cabin
Front of Lake Jeff Cottage showing two of the three floors in the cottage.
Lake view from the bluestone terrace, steps outside your door.
Stone Terrace and lounge area overlooking Lake Jeff.
Front view of Lake Jeff Cottage with the lake in the background
Exceptional
(103 reviews)

Private Lakefront Cottage, Panoramic Lake Views. Fish, Row, Kayak, Pet-Friendly

Jeffersonville

8% off
AU$4,327
for 7 nights, 1 home
AU$618 per night
includes taxes & fees
Private Lakefront Cottage, Panoramic Lake Views. Fish, Row, Kayak, Pet-Friendly
Head upstairs for bedroom privacy
Private lakefront deck for sunrise coffee, afternoon lounging & sunset cocktails
Gather around the kitchen island for breakfast, wine, or shared meals
Original Victorian staircase that preserves the home’s historic charm
Exceptional
(9 reviews)

Victorian Lake Oasis | Hot Tub | Private Lakefront

Damascus

7% off
AU$2,822
for 7 nights, 1 home
AU$403 per night
includes taxes & fees
Victorian Lake Oasis | Hot Tub | Private Lakefront

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to historical Callicoon

Enjoy the area's history, entertainment and opera with a rental holiday home in Callicoon. Renowned for its wildlife, gardens and forests, this city welcomes all visitors. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Callicoon

Are you looking for attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that makes Callicoon a fun place to get away to. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Sullivan County Golf and Country Club (15.3 mi / 24.7 km)
  • Ski Big Bear at Masthope Mountain (16.7 mi / 26.9 km)
  • Carousel Water and Fun Park (12.7 mi / 20.5 km)
  • Honesdale Golf Club (16.9 mi / 27.2 km)
  • Hancock Golf Course (17.9 mi / 28.7 km)
  • Hancock Golf & Country Club (18 mi / 28.9 km)

Exploring the natural features in Callicoon

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Callicoon. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Tennanah Lake (9.3 mi / 14.9 km)
  • Woodstock Monument (10.1 mi / 16.2 km)
  • Upper Delaware River (10.9 mi / 17.5 km)
  • Lake Superior State Park (11.3 mi / 18.3 km)
  • Lake Teedyuskung (17.3 mi / 27.9 km)
  • Hancock Town Square (17.4 mi / 28 km)

Frequently asked questions

What is the best area to stay in Callicoon when booking a holiday rental?
When considering the best area to stay in Callicoon for a holiday rental, the charming neighbourhoods along the Delaware River are particularly delightful. This picturesque part of town offers a serene atmosphere, great for those looking to escape the hustle and bustle of daily life. The riverfront not only provides stunning views but also opportunities for kayaking and fishing, making it ideal for outdoor enthusiasts.Another appealing area is the quaint main street, where you'll find a delightful mix of local shops, cafes, and restaurants. This vibrant stretch is great for leisurely strolls, and you can stop by the local farmers' market if you're visiting during the summer months. Callicoon is also known for its proximity to the scenic Catskills, which feature hiking trails and breathtaking vistas, great for nature lovers.Although specific property numbers can fluctuate, the community typically offers a variety of rental options, from cosy cabins to charming cottages, ensuring that visitors can find something that suits their preferences.
Where are the best Callicoon ski resort rentals?
For the best ski resort rentals near Callicoon, New York, travellers should consider accommodations in the nearby Catskills region, particularly around the town of Jeffersonville and the small community of Barryville. These areas provide convenient access to the ski slopes, with many properties offering a range of amenities suitable for winter sports enthusiasts.In Jeffersonville, you can find a variety of lodgings, including charming cabins and modern chalets. Many of these rentals feature essentials such as fully equipped kitchens, spacious living areas with fireplaces, and outdoor decks that allow for relaxation after a day on the slopes. Some properties may also include amenities like hot tubs, great for unwinding under the stars.Barryville, located along the Delaware River, offers a selection of unique stays such as converted barns and riverside cottages. These accommodations often come with picturesque views, access to nearby hiking trails, and easy proximity to local dining options. The rustic charm of the area complements the outdoor experience, making it ideal for those looking to enjoy both skiing and the natural beauty of the region.Additionally, the nearby ski areas, such as Holiday Mountain Ski and Fun Park, provide family-friendly slopes and facilities, enhancing the overall winter getaway experience.
What is the most popular type of holiday rental accomodation in Callicoon?
In Callicoon, holiday houses are the most popular type of holiday rental, with around 48 available throughout the area. These properties typically offer spacious living areas, fully equipped kitchens, and often include outdoor spaces such as decks or patios, superb for enjoying the picturesque views of the Delaware River and the surrounding countryside. Additionally, there are several charming cottages scattered across the region, providing a cozier, more intimate atmosphere for couples or small families looking to escape into nature.
Are there any family house rentals in Callicoon?
In Callicoon, New York, there are several family-friendly house rentals available, making it a charming spot for family getaways. Visitors can find accommodations in picturesque neighbourhoods that provide a tranquil atmosphere, superb for relaxation after exploring the area. Many of these homes feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can enjoy the fresh air and play.The locale is renowned for its beautiful natural surroundings, with access to the Delaware River for fun-filled days of swimming and fishing. Nearby, the charming town centre offers quaint shops and local eateries, adding to the appeal of this destination.
Can I rent a holiday home with a pool or hot tub in Callicoon?
In Callicoon, there are several holiday homes available for rent that feature pools or hot tubs. This charming town, located in the heart of the Catskills, offers a mix of rustic charm and modern amenities, making it an appealing destination for travellers seeking relaxation. Many of the properties come equipped with private pools, hot tubs, and outdoor entertaining areas, great for enjoying the scenic surroundings.Most rentals also offer fully equipped kitchens, spacious living areas, and amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay. Additionally, the nearby Delaware River provides opportunities for outdoor activities, including fishing and kayaking, adding to the appeal of a holiday in Callicoon.
Are there pet-friendly house rentals in Callicoon?
In Callicoon, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to bring their furry companions along. The area features charming holiday homes that often include amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like decks or gardens where pets can enjoy the fresh air.Located near the scenic Delaware River, many of these rentals provide easy access to walking paths and nature trails, great for leisurely strolls with pets. The surrounding countryside offers picturesque views and opportunities for outdoor activities, making it an ideal setting for a relaxing getaway. Additionally, the local community is welcoming to pets, with various pet-friendly cafes and shops enhancing the overall experience for visitors.
Are there any remote work holiday rentals in Callicoon?
In Callicoon, New York, there are a variety of remote work-friendly holiday rentals available, with around 48 options to choose from. This charming town, located along the Delaware River, offers a peaceful setting that is ideal for those looking to combine work and leisure. Many of the properties come equipped with essential amenities for remote work, such as high-speed internet and dedicated workspace, including desks and ergonomic chairs. Some rentals even provide additional features like computer monitors to enhance productivity.Aside from the work-friendly features, travellers can enjoy the scenic beauty of the Catskill Mountains and the nearby river for outdoor activities during their downtime. The town itself has a quaint atmosphere, with local shops and eateries that add to the experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Callicoon?
In Callicoon, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals, and outdoor spaces such as decks or patios for enjoying the fresh air. Many properties also offer onsite parking, providing convenience for those travelling by car. Additionally, rentals typically feature coffee and tea makers, superb for starting the day with a warm beverage.
When is the best time to visit Callicoon for a holiday rental?
The best time to visit Callicoon for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period draws visitors looking to enjoy the lush landscapes and warm weather, superb for outdoor activities like hiking along the Delaware River or exploring the charming local shops and cafés.During these summer months, temperatures typically range from 20 to 30 degrees Celsius, creating an inviting environment for those keen on soaking up the sun. The area buzzes with energy as festivals and community events take centre stage, offering a taste of local culture that you won't want to miss.If you're considering a more budget-friendly option, November is a wonderful time to visit Callicoon. This month is quieter, allowing you to appreciate the serene beauty of the changing seasons without the hustle and bustle of peak tourist traffic. You can enjoy the picturesque landscapes adorned with autumn colours and the peaceful atmosphere that comes with it.Ultimately, your choice of when to visit Callicoon will depend on whether you prefer the lively summer scene filled with outdoor adventures or the tranquil charm of the fall.
What are the top attractions in Callicoon?
In Callicoon, visitors can enjoy a charming blend of outdoor activities and local culture. The Delaware River offers opportunities for kayaking, fishing, and scenic walks along its banks. The picturesque Main Street features quaint shops and eateries, making it a lovely spot to explore. Nearby, the Callicoon Theater, a historic venue, showcases independent films and provides a unique cultural experience. For nature enthusiasts, the surrounding Catskill Mountains present hiking trails and stunning vistas, superb for a day of adventure.
Are all fees included in the Callicoon holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Callicoon holiday homes with parking?
Stayz offers a wide selection of holiday homes in Callicoon with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Callicoon holiday homes?
You can find great discounts on holiday homes in Callicoon on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Callicoon holiday home booking on Stayz?
To find Callicoon holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Callicoon?
A long-stay holiday home in Callicoon is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Callicoon holiday home?
Book your Callicoon holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Callicoon?
Prices for holiday homes in Callicoon vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Callicoon to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.