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Cupar holiday lettings

We found 1,222 holiday rentals — enter your dates for availability

Select from 28 homes, 72 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.

Holiday rentals with weekly discounts - Cupar

Showing deals for:6 Mar - 13 Mar

Image gallery for Harbour Cottage - One Bedroom (Sleeps 2)

Harbour cottage is a short walk to the historical harbour in Crail
9.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Harbour Cottage - One Bedroom (Sleeps 2)

Anstruther, SCT

17% off
Price is £925
for 7 nights, 1 cottage
£132 per night
includes taxes & fees
Harbour Cottage - One Bedroom (Sleeps 2)

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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:

  • Raptor World Interactive (3.2 mi / 5.1 km)
  • St. Andrews Links (7.7 mi / 12.3 km)
  • St Andrews - Jubilee Course (7.9 mi / 12.8 km)
  • Old Course at St Andrews (8.1 mi / 13.1 km)
  • Royal & Ancient Golf Club of St. Andrews (8.1 mi / 13.1 km)
  • St. Andrews Aquarium (8.2 mi / 13.2 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:

  • 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)
  • Dundee Law (10.4 mi / 16.7 km)
  • Lomond Hills (11 mi / 17.7 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, a popular area to stay is the charming town centre. This vibrant location offers a delightful blend of local shops, cafes, and restaurants, making it a convenient base for exploring the surrounding region. The town centre is home to top attractions such as the historic Cupar Old Parish Church, which boasts stunning architecture and a rich history, and the nearby Cupar Golf Club, a beautiful spot for golf enthusiasts and those who enjoy scenic walks.

Another excellent area to consider is the outskirts of Cupar, particularly near the picturesque countryside. This setting provides a tranquil atmosphere and easy access to the stunning landscapes of the Fife countryside. Visitors can enjoy walking and cycling trails, with the nearby Lomond Hills Regional Park offering breathtaking views and outdoor activities.
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, travellers should consider the nearby coastal areas of St Andrews and the picturesque village of Anstruther. St Andrews, known for its historic university and stunning beaches, offers a variety of holiday rentals that provide stunning views of the North Sea. Many properties in this area come equipped with modern amenities such as spacious living areas, fully equipped kitchens, and outdoor terraces or gardens, superb for enjoying the coastal scenery.

Anstruther, a charming fishing village, is another excellent option, where visitors can find quaint cottages and larger family homes. These rentals often feature traditional decor, cosy fireplaces, and easy access to the beach, along with nearby seafood restaurants and local shops. The picturesque harbour and its lively atmosphere make it a delightful choice for those looking to immerse themselves in a seaside experience.
What is the most popular type of holiday rental accomodation in Cupar?
In Cupar, cottages are the most popular type of holiday rental, with approximately 64 available throughout the area. These charming properties often feature traditional architecture and are situated in picturesque surroundings, great for those looking to experience the Scottish countryside. Most cottages come equipped with fully fitted kitchens, cosy living areas, and outdoor spaces where guests can enjoy the fresh air while taking in the scenic views of the surrounding landscape.
Are there any family house rentals in Cupar?
In Cupar, Scotland, there are numerous family-friendly house rentals available, with around 40 options to choose from. This charming town offers a mix of properties that cater to families, featuring spacious living areas and well-equipped kitchens ideal for preparing meals together. Many homes come with outdoor spaces where children can play and families can enjoy al fresco dining.
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 several pet-friendly house rentals available, making it a welcoming destination for travellers with pets. Many of these properties come equipped with essential amenities such as fully stocked kitchens, comfortable living spaces, and private outdoor areas where pets can roam freely.

The town itself is steeped in history and offers a charming environment, with easy access to local parks and green spaces that are great for walks with your furry companions. Not far from Cupar, you can explore the scenic beauty of the nearby Lomond Hills Regional Park, which features a variety of trails suitable for both hiking and leisurely strolls, enhancing your outdoor experience with pets. See all pet-friendly rentals in Cupar.
Are there any remote work holiday rentals in Cupar?
In Cupar, Scotland, there is a wide selection of remote work holiday rentals available, with around 104 options to choose from. This charming town offers a tranquil environment for those looking to work away from home. Many properties come equipped with essential amenities including Wi-Fi, desks, and comfortable chairs, ensuring a productive workspace. 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 rental amenities typically include a fully equipped kitchen, allowing guests to prepare their own meals during their stay. Many properties feature complimentary Wi-Fi, essential for those wanting to stay connected or plan their daily activities. Additionally, rentals often come with a microwave and cookware, dishware, and utensils, making it convenient for travellers to dine in.
When is the best time to visit Cupar for a holiday rental?
September is the most popular month to visit Cupar, making it an ideal time for travellers seeking a blend of culture and the stunning Scottish countryside. During this period, the charming town comes alive with various local events, and the weather is typically mild, with average temperatures in the low teens Celsius. This creates a comfortable environment for outdoor activities such as hiking in the nearby hills or strolling through the picturesque streets of Cupar.

The peak season runs from July to September, attracting visitors who enjoy the vibrant atmosphere of summer festivals and the lush greenery of the surrounding landscapes. This is the superb time to engage in outdoor pursuits, explore historical sites, or simply relax in the scenic beauty of Fife.

For those looking for a more budget-friendly option, December offers a quieter experience with fewer crowds, allowing for more intimate exploration of the area. While temperatures can dip to around 3-5 degrees Celsius, the festive spirit and local holiday events provide a unique charm that makes visiting Cupar during this time quite special.
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, Scotland, visitors can discover several popular attractions that highlight the town's rich history and charming character. The Cupar Heritage Centre offers insights into the local history, showcasing exhibits that delve into the town's past. Nearby, the historic St. John's Church, with its impressive architecture, is a must-see.

For those interested in the outdoors, the scenic countryside surrounding Cupar provides ample opportunities for walking and cycling, especially along the picturesque paths of the nearby Lomond Hills. The town is also a short drive from the stunning coastline of Fife, where attractions like the beautiful beaches of St Andrews can be easily accessed.
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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