Photo by Craig Cullinane

Cupar holiday lettings

We found 1,274 holiday rentals — enter your dates for availability

Select from 31 homes, 68 cottages and other holiday rentals in Cupar to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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Why visit Cupar

  • Rich history: Explore historic colleges, universities, and impressive castles that reflect Cupar's cultural heritage.
  • Outdoor activities: Enjoy a range of adventures in stunning natural surroundings, perfect for families and thrill-seekers alike.
  • Charming accommodation: Stay in delightful holiday cottages, spacious apartments, and private homes tailored to your needs.
  • Friendly atmosphere: Experience the warm hospitality of the locals as you wander through this picturesque town.
  • Beach access: Take day trips to beautiful nearby beaches for relaxation and seaside fun.

Popular types of accommodation in Cupar

If you're planning a getaway to Cupar, the excitement begins with selecting your ideal accommodation. From cosy cottages to spacious apartments and private holiday homes, you'll find a range of options to suit your needs. Whether you're after a charming cottage or a comfortable house rental, Cupar offers a delightful selection of vacation rentals to ensure a memorable stay.

  • Apartments: The top choice for visitors to Cupar, offering modern amenities and convenient locations for a comfortable stay.
  • Houses: Ideal for families or groups, these homes provide a home-away-from-home experience with ample space and privacy.
  • Cottages: Quaint and charming, these properties are perfect for those seeking a cosy retreat in the picturesque Scottish countryside.
  • Guest Houses: A welcoming option, providing a friendly atmosphere and often including breakfast for a delightful start to your day.
  • Condos: Offering a blend of comfort and convenience, condos make for a great choice for those looking for a more spacious option.**

Top attractions in and around Cupar

Cupar, Scotland, offers a delightful mix of outdoor adventures and cultural experiences, making it perfect for an active holiday. Visitors can explore beautiful beaches, historic colleges and universities, and impressive castles. Whether you’re seeking a beach day or a taste of history, Cupar’s attractions cater to all interests, ensuring a memorable visit for every traveller.

  • University of St. Andrews: This historic university, located 4.3km from Cupar, boasts stunning architecture and a rich academic heritage. Explore its beautiful campus and immerse yourself in the vibrant culture that has shaped many influential figures.
  • Falkland Palace: Situated within Cupar, this stunning historic palace features exquisite gardens and captivating architecture. It offers a glimpse into royal history and the lifestyle of Scottish nobility, set in a picturesque village.
  • St. Andrew's Cathedral: Located 5.6km from Cupar, these impressive ruins are steeped in history. Once a grand symbol of ecclesiastical power, the site provides a serene atmosphere and breathtaking views over the surrounding area.

Things to do recommended for couples

For a romantic getaway in Cupar, visit Cairn O'Mohr Fruit Wines for a delightful winery experience, or enjoy a meal at Potter About, perfect for couples. Don't miss St Andrews Wine Company, where you can savour fine wines amidst beautiful outdoor settings.

Things to do recommended for families

Families will relish a day at Craigtoun Country Park, just 4.3km from Cupar, offering delightful outdoor activities. Alternatively, visit East Sands, 5.6km away, for a relaxing beach experience, or catch a match at Tannadice Park, located 6.8km from Cupar for a taste of local sports.

Things to do recommended for groups

Groups visiting Cupar can enjoy a round of golf at the renowned Old Course in St Andrews, hike the scenic Fife Coastal Path, and play golf at St Andrews Bay, all while soaking up the beautiful outdoor surroundings and vibrant sports atmosphere.

What do I need to keep in mind when booking a vacation in 'Cupar

When travelling with a group, family, or pets, or if you're seeking extended stays, it's essential to refine your search according to your specific needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Cupar with a group: Think about how many bedrooms you’ll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Cupar with young kids: Journeying with little ones can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities, such as a private swimming pool. Additionally, it would be wise to think about your closeness to attractions that are suitable for families.
  • Taking your pets with you to Cupar: For many, a family holiday isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Cupar: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Cupar

Cupar, nestled in central Scotland, offers an enchanting mix of adventure and history for travellers. With its friendly atmosphere, you can explore charming holiday cottages and enjoy short stays in this delightful town. Venture into the surrounding regions for outdoor activities, family-friendly excursions, and a chance to unwind in picturesque settings. Whether you're seeking relaxation or adrenaline, Cupar is the perfect base for a memorable Scottish getaway.

  • Falkland: Nestled in the picturesque countryside near Cupar, Falkland is a charming village renowned for its stunning outdoor experiences. Visitors are drawn to the area for its scenic hiking trails and recreational spaces that promise adventure and breathtaking views. Key attractions include the remarkable Falkland Palace, a historic royal residence, and the nearby monument that adds a touch of local history. The tranquil private gardens offer a perfect spot for a leisurely stroll, making Falkland a delightful retreat for nature lovers and history enthusiasts alike.
  • Ceres: Just a short distance from Cupar, Ceres is a quaint village that beautifully combines outdoor adventure with cultural experiences. The area is ideal for hiking and exploring trails, while golf enthusiasts will find excellent courses to enjoy. Ceres is also home to notable landmarks such as its charming streets and private gardens, which exemplify the village's rich heritage. Visitors can immerse themselves in local culture, making Ceres a must-visit destination for those seeking both relaxation and exploration.
  • Ladybank: Located conveniently near Cupar, Ladybank is a vibrant village that offers a unique blend of cultural and outdoor activities. The local theatre provides entertainment for those looking to enjoy the arts, while golf courses cater to sports enthusiasts. Ladybank's historic sites, including a striking castle and a historic house, invite visitors to delve into the area’s fascinating past. The lovely private gardens add to the charm of this village, making it an inviting spot for travellers seeking both leisure and cultural enrichment.

Best time to go to Cupar

If you're planning a trip to Cupar, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in February, July and September, while off-peak times, like May, October and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.0°F (3.9°C)Light RainMostly CloudyAverageSlightly Low
February39.9°F (4.4°C)Light RainMostly CloudySlightly HighSlightly Low
March41.9°F (5.5°C)Light RainMostly CloudyAverageSlightly Low
April45.0°F (7.2°C)No Rain (Dry)Mostly SunnyAverageAverage
May49.6°F (9.8°C)Light RainMostly CloudySlightly LowAverage
June54.5°F (12.5°C)Light RainMostly CloudyAverageSlightly High
July57.9°F (14.4°C)Light RainMostly CloudySlightly HighSlightly High
August57.6°F (14.2°C)Light RainMostly CloudyAverageSlightly High
September54.5°F (12.5°C)Light RainMostly CloudySlightly HighAverage
October49.8°F (9.9°C)Light RainMostly CloudySlightly LowAverage
November44.2°F (6.8°C)Light RainMostly CloudyAverageAverage
December40.3°F (4.6°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can really make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for you to plan new trips, resume your previous arrangements, or organise your travel plans effortlessly. You can easily access your saved or booked properties, which are sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Travel to cosy Cupar

Enjoy the history and other features of Cupar. Travellers to this relaxing city praise the golfing, fishing and bars. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Cupar

Do you want to find attractions to see while you're in town? Venture out of your holiday home and experience everything that Cupar has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • The Scottish Deer Centre (3.2 mi / 5.1 km)
  • St. Andrews Links (7.7 mi / 12.3 km)
  • Old Course at St Andrews (8.1 mi / 13 km)
  • Royal & Ancient Golf Club of St. Andrews (8.1 mi / 13.1 km)
  • St. Andrews Aquarium (8.2 mi / 13.2 km)
  • St Andrews - Eden Course (8.5 mi / 13.7 km)

Exploring the natural landscape of Cupar

Whether you're an active traveller or just want to spend some time taking in the scenery, Cupar is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Craigtoun Country Park (6.5 mi / 10.5 km)
  • Backhouse Rossie Estate (7 mi / 11.3 km)
  • West Sands (8 mi / 13 km)
  • Leven Beach (8.7 mi / 14 km)
  • Falkland Palace (8.7 mi / 14.1 km)
  • Fife Coastal Path (9 mi / 14.4 km)

Travelling to and around Cupar

The nearest airport is in Dundee (DND), located 9.3 mi (14.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Edinburgh Airport (EDI), which is 29.1 mi (46.8 km) away.

If you prefer to travel by train, Cupar Station, Springfield Station and Ladybank Station are the main stations that serve the city.

Frequently asked questions

What is the best area to stay in Cupar when booking a holiday rental?
When considering a holiday rental in Cupar, Scotland, the town centre offers a delightful blend of convenience and charm. Staying here means you are just a short stroll away from quaint shops, local cafes, and vibrant markets, providing an authentic Scottish experience.

In terms of attractions, the historic Cupar Old Parish Church is a must-see, showcasing stunning architecture and a rich history. Additionally, the nearby Hill of Tarvit Mansion and Garden is a wonderful place to explore, featuring beautiful landscapes and an impressive collection of art and antiques.

The town centre has a variety of properties available, ranging from cosy flats to spacious family homes, suiting different needs and preferences.
How much does it cost to rent a holiday home in Cupar?
Prices for holiday rentals in Cupar 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cupar to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cupar holiday house rentals?
You can find great discounts on house rentals in Cupar on Vrbo, 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.
Where are the best areas for renting a beach house in Cupar?
For renting a beach house in Cupar, Scotland, the nearby coastal town of St Andrews is an excellent option. Known for its historic university and beautiful beaches, St Andrews offers a variety of holiday rentals, many of which provide stunning views of the North Sea. Properties in this area often include amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces for dining, making them suitable for families or groups.

Another appealing area is the picturesque village of Crail, located along the East Neuk of Fife. Here, you can find charming cottages and traditional fisherman's houses that often feature unique character, with cosy interiors and modern conveniences. Many rentals come with features like private gardens or patios, superb for enjoying the coastal scenery.

Additionally, the nearby beaches at Elie and Anstruther are worth considering, where you can find beach houses that provide easy access to sandy shores and local attractions. These properties typically have amenities such as barbecue facilities, outdoor seating, and proximity to local shops and restaurants that serve fresh seafood.
What is the most popular type of holiday rental accomodation in Cupar?
In Cupar, cottages are the most popular type of holiday rental, with around 153 available across the charming town and its surrounding countryside. These cottages typically feature traditional decor, fully equipped kitchens, and inviting living areas, providing a cosy atmosphere for guests. Many come with outdoor spaces such as gardens or patios, superb for enjoying the picturesque Scottish landscape.

For those seeking more space, there are about 81 holiday houses that offer multiple bedrooms and larger living areas, suiting families or groups. Additionally, approximately 33 apartments can be found in the area, providing modern amenities and convenient access to local shops and attractions. A smaller selection of cabins and villas—18 of each—offers unique stays for travellers looking for something different.
Are there any family house rentals in Cupar?
In Cupar, Scotland, there is a good selection of family-friendly holiday rentals, with around 44 options available throughout the area. Visitors can expect spacious homes featuring multiple bedrooms, ideal for accommodating families. Many of these properties include amenities such as fully equipped kitchens, allowing for convenient meal preparation, and comfortable living areas where families can relax together.

The town is situated near several attractions, including the historic landmarks of St Andrews, which is just a short drive away. Families can explore the stunning beaches or enjoy outdoor activities in the surrounding countryside, making it a great base for a memorable family holiday.
Can I find long-stay holiday rentals in Cupar?
A long-stay holiday rental in Cupar 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Cupar?
In Cupar, there are numerous pet-friendly house rentals available, making it an excellent choice for travellers with pets. The area offers a variety of amenities, with many holiday homes featuring fully equipped kitchens, spacious living rooms, and outdoor spaces, ideal for enjoying the fresh Scottish air. Some properties may also include private gardens or patios where pets can roam freely, enhancing the overall experience for pet owners.

Cupar is situated in the picturesque Fife region, close to several parks and natural attractions. For instance, the nearby Craigtoun Country Park is a wonderful spot for leisurely walks and picnics, allowing pets to enjoy the outdoors alongside their owners. Additionally, the charming countryside surrounding Cupar provides ample opportunities for scenic walks and exploration. See all pet-friendly rentals in Cupar.
Are there any remote work holiday rentals in Cupar?
In Cupar, Scotland, there are numerous options for remote work holiday rentals, with around 294 properties available to suit various needs. Many of these accommodations are well-equipped with amenities conducive to working remotely, such as free Wi-Fi both in individual rooms and in public areas.

Travellers can expect comfortable living spaces that often include dedicated work areas, allowing for a productive environment. You'll find a mix of charming cottages and modern apartments, often featuring fully equipped kitchens, making it easy to prepare meals during longer stays. The town itself is steeped in history, providing a lovely backdrop for breaks from work, with nearby attractions including the beautiful Cupar Golf Club and the scenic landscapes of the Fife countryside, great for leisurely walks after a day of remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cupar holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Cupar 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 on Vrbo 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.
What are popular rental amenities in Cupar?
In Cupar, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also offer onsite parking, which is a convenient feature for those travelling by car. Pet-friendly options are available, welcoming furry companions, along with accommodations that permit service animals. Additionally, many rentals come with a fireplace, providing a warm and inviting atmosphere, especially during the cooler months.
When is the best time to visit Cupar for a holiday rental?
September is the most popular time to visit Cupar, Scotland, as the summer crowds begin to dwindle, allowing for a more relaxed atmosphere. The peak season runs from July to September, where visitors can enjoy the lush green landscapes and vibrant local culture. During these months, the weather is typically mild with average temperatures ranging from 10 to 20 degrees Celsius, making it ideal for outdoor activities such as hiking and exploring the charming town.

In September, you can immerse yourself in the local events and festivals that often take place, showcasing Cupar's rich history and community spirit. The comfortable climate invites leisurely strolls through the picturesque streets or visits to the nearby historical sites, all while avoiding the busier tourist season.

If you're looking for a more budget-friendly option, consider visiting in December. While this is the low season, it offers a unique charm with festive decorations and a quieter ambience superb for cosy getaways. You can explore the town's attractions at a leisurely pace and enjoy the warmth of local hospitality without the hustle and bustle of peak season.
How early should I book a Cupar holiday rental?
Book your Cupar holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Cupar?
In Cupar, visitors can discover a charming blend of history and natural beauty. The town centre features the historic Cupar Castle, where remnants of its medieval past can be explored. Nearby, the impressive St. John's Church offers a glimpse into the town's architectural heritage.

For nature enthusiasts, the surrounding countryside provides stunning walking trails, particularly around the nearby Lomond Hills Regional Park, which is great for hiking and enjoying the scenic landscapes. Additionally, the picturesque village of Falkland, just a short drive away, is home to the magnificent Falkland Palace, a former royal residence set within beautiful gardens.
Can I change or cancel my Cupar home rental booking on Vrbo?
To find Cupar holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Cupar holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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