Photo by Craig Cullinane

Cupar vacation rentals

We found 1,246 vacation rentals — enter your dates for availability

Select from 32 homes, 70 cottages, and other vacation rentals in Cupar to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll find the best amenities for hanging out with the people that matter most, such as air conditioning and a TV. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Cupar

Showing deals for:Apr 3 - Apr 10

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

Harbour Cottage nestled against the castle wall and on the coastal path.
9.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Harbour Cottage - One Bedroom (Sleeps 2)

Crail

17% off
Price is $205
$1,432 for 7 nights
All fees included
Harbour Cottage - One Bedroom (Sleeps 2)

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Find out more about Cupar

Why visit Cupar

  • Outdoor Adventures: Cupar is perfect for nature lovers, offering numerous parks and outdoor activities for all ages.
  • Rich History: Explore nearby historic sites, including castles and universities that showcase Scotland's heritage.
  • Charming Accommodations: Choose from cozy cottages, spacious homes, or comfortable apartments to enhance your stay.
  • Friendly Atmosphere: Experience the warm hospitality of locals in this welcoming town, ideal for families and groups.
  • Scenic Beaches: Enjoy nearby beaches for relaxation and recreation, adding variety to your vacation experience.

Popular types of accommodation in Cupar

If you're exploring Cupar for your next getaway, you'll find a variety of cozy accommodations to choose from. The most popular options include charming cottages, spacious houses, and comfortable apartments. Whether you're searching for a quaint cottage rental for a romantic escape or a larger house rental for family gatherings, Cupar has something to suit every traveler's needs.

  • Apartments: The top choice for vacation rentals in Cupar, offering convenience and comfort for travelers.
  • Houses: A great option for families or groups, providing a home-like atmosphere during your stay.
  • Cottages: Charming and cozy, these rentals offer a quaint experience, perfect for a peaceful getaway.
  • Guest Houses: A welcoming choice with personal touches, ideal for those seeking a friendly environment.
  • Condos: These modern spaces provide amenities and a stylish setting for your vacation in Cupar.**

Top attractions in and around Cupar

Cupar, Scotland, is an ideal destination for outdoor and adventure enthusiasts, offering a blend of cultural experiences and natural beauty. Visitors can explore historic sites such as castles and universities, while nearby beaches provide opportunities for relaxation and recreation. Additional attractions include boat rentals and charming stone cottages, making Cupar a perfect spot for a memorable vacation filled with diverse activities and scenic sights.

  • University of St. Andrews: This historic university, located 7 miles from Cupar, is the oldest in Scotland, offering a unique blend of medieval architecture and vibrant student life. Explore its picturesque campus and soak in the rich academic culture.
  • Falkland Palace: Situated within Cupar, this stunning historic palace boasts beautiful gardens and fascinating history. Once a royal residence, it invites visitors to wander through its opulent rooms and enjoy the tranquil surroundings.
  • St. Andrew's Cathedral: These impressive ruins, located 9 miles from Cupar, are a testament to Scotland's ecclesiastical heritage. Marvel at the remnants of this grand structure while enjoying the serene atmosphere of the site.

Things to do recommended for couples

For a romantic getaway in Cupar, visit Cairn O'Mohr Fruit Wines for a delightful winery experience or explore St Andrews Wine Company, perfect for outdoor vibes. For a touch of luxury, enjoy a round at Ballumbie Castle Golf Course, just a short drive away.

Things to do recommended for families

Families can explore the natural beauty at Craigtoun Country Park, unwind at East Sands recreation center, or catch a thrilling game at Tannadice Park. Each location offers a unique experience, perfect for creating lasting memories together while enjoying the charm of Cupar.

Things to do recommended for groups

Groups visiting Cupar can enjoy a round of golf at the historic Old Course in St Andrews, just 8 miles away, or explore the scenic St Andrews Bay, 10 miles distant. For a unique experience, visit the romantic Eden Mill St Andrews distillery, located 5 miles from Cupar.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, or pets, or if you're considering extended stays, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Cupar with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Cupar with young kids: Traveling with little ones can be quite the adventure. It's important to prioritize their comfort and safety, along with finding amenities suited for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Cupar: For many families, a trip isn't truly enjoyable without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cupar: If you're in search of vacation rentals with discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Cupar

Cupar, Scotland, offers a delightful blend of outdoor adventure and historical charm. Explore nearby towns and neighborhoods, where friendly locals create a welcoming atmosphere perfect for families and excursions. Enjoy a charming getaway with local amenities and experience the vibrant mix of relaxation and adventure. From scenic parks to historical sites, Cupar is the ideal base for your vacation, ensuring unforgettable memories in this captivating region.

  • Falkland: Nestled in the picturesque countryside near Cupar, Falkland is a charming village that offers a blend of outdoor adventure and stunning scenery. Known for its hiking trails and golf course, Falkland invites visitors to explore its natural beauty. Don't miss the chance to visit local landmarks such as the historic Falkland Palace, a stunning example of Renaissance architecture, and the nearby private gardens that showcase the region's horticultural charm. Whether you're hiking up to the monument overlooking the village or enjoying a leisurely round of golf, Falkland is a delightful escape for nature lovers.
  • Ladybank: A vibrant village situated close to Cupar, Ladybank is a great destination for those seeking cultural experiences and outdoor entertainment. The village is home to a renowned golf course and an active theater scene that offers a variety of performances. Enjoy the scenic trails that wind through the area, perfect for walking or cycling. Key attractions include historic houses and beautifully maintained private gardens, providing a glimpse into the village's heritage. With its friendly atmosphere and engaging activities, Ladybank promises a fulfilling visit for all.
  • Ceres: Ceres is another delightful village in the Cupar area, known for its rich culture and adventurous spirit. Visitors can take advantage of the extensive trail access for hiking or cycling, or enjoy a round of golf amidst breathtaking landscapes. The village is also home to several monuments and quaint streets that invite exploration. Be sure to check out the local private gardens, which reflect the community's dedication to preserving its natural beauty. Ceres offers a unique combination of outdoor fun and cultural experiences, making it a must-visit during your stay.

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 a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect spot.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. It truly benefits you to take on the role of organizer. Enroll in our One Key rewards program to enjoy exclusive savings available only to members and start accumulating OneKeyCash on eligible stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan future adventures, pick up right where you left off, or manage your travel arrangements. You can easily access the properties you’ve saved or booked in sections like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to cozy Cupar

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

Sightseeing in and around Cupar

Are you searching for things to do while you're in the area? Venture out of your vacation home and experience everything that Cupar has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Raptor World Interactive (3.2 mi / 5.1 km)
  • St. Andrews Links (7.7 mi / 12.3 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 Bay (10.3 mi / 16.5 km)
  • Camperdown Wildlife Centre (11.2 mi / 18 km)

Exploring the natural landscape of Cupar

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Cupar is a great place to get out in nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Lochee Park (10.2 mi / 16.3 km)

Traveling to and around Cupar

The nearest airport is in Dundee (DND), located 9.3 mi (14.9 km) from the city center. 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 in the city.

Frequently asked questions

What is the best area to stay in Cupar when booking a vacation rental?
When considering a vacation rental in Cupar, Scotland, the town center is an excellent area to stay. This vibrant part of Cupar offers a lovely blend of historical charm and modern amenities, making it convenient for exploring the local culture. You'll find a variety of dining options, quaint shops, and easy access to attractions such as the stunning Cupar Golf Club, which is great for enthusiasts seeking a round of golf amidst beautiful scenery. Additionally, the nearby historic structures like the Cupar Old Parish Church provide a glimpse into the town's rich heritage.

Another appealing option is the neighborhood around the picturesque Cupar Castle. This area is quieter and provides a more residential feel, with easy access to the surrounding countryside. Here, you can enjoy leisurely walks while admiring the natural beauty of the region. The proximity to the picturesque countryside trails makes it ideal for those who love outdoor activities.
How much does it cost to rent a vacation home in Cupar?
Prices for vacation 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 vacation 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, consider the nearby coastal towns of St. Andrews and Anstruther, both offering stunning seaside views and charming accommodations. St. Andrews, known for its historic university and picturesque beaches, features a variety of vacation rentals that often come equipped with amenities like large outdoor terraces, barbecue facilities, and fully furnished kitchens. Many properties are within walking distance of the famous West Sands beach, ideal for long walks or picnics by the sea.

Anstruther, a quaint fishing village, is another excellent option, where travelers can find cozy cottages overlooking the harbor. These rentals typically provide modern conveniences such as Wi-Fi, laundry facilities, and some even boast private gardens or patios for enjoying the coastal breeze. The area is also renowned for its fish and chip shops and local seafood restaurants, offering a taste of Scotland's culinary delights.

Additionally, the nearby Fife Coastal Path offers a chance for outdoor enthusiasts to explore scenic walks along the coastline, with many rentals situated conveniently for access to these trails.
What is the most popular type of vacation rental accomodation in Cupar?
In Cupar, cottages are the most popular type of vacation rental, with around 59 available throughout the charming town and surrounding countryside. These cottages often feature traditional decor, fully equipped kitchens, and cozy living areas, making them great for travelers seeking a homey atmosphere. Many also include outdoor spaces such as gardens or patios, ideal for enjoying the scenic views of the Scottish landscape.

In addition to cottages, there are about 25 vacation houses that provide ample space for larger groups or families. These homes typically offer multiple bedrooms, spacious living areas, and modern amenities.
Are there any family house rentals in Cupar?
In Cupar, Scotland, families will find an abundance of rental options, with around 42 properties suiting their needs. This charming town offers a selection of spacious homes that provide an inviting space for larger groups. Many of these accommodations boast full kitchens, inviting living rooms, and outdoor spaces superb for children to play.

Located near the picturesque town center, visitors can explore local parks and enjoy the scenic beauty of the surrounding countryside, which includes walking trails and historical sites. The nearby East Neuk of Fife, known for its stunning coastal views and quaint fishing villages, is also easily accessible, making it an ideal day trip for families looking to experience a bit of adventure.
Can I find long-stay vacation rentals in Cupar?
A long-stay vacation rental in Cupar is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Cupar?
In Cupar, there are numerous pet-friendly house rentals available, providing a welcoming environment for travelers with furry companions. Many of these rentals come equipped with essential amenities such as fully stocked kitchens, comfortable living areas, and outdoor spaces where pets can enjoy fresh air.

The town is conveniently located near several parks and green spaces, making it easier for pet owners to find suitable places for walks and play. Additionally, the surrounding Fife countryside offers scenic trails and open areas great for outdoor adventures with pets.
Are there any remote work vacation rentals in Cupar?
In Cupar, Scotland, there are numerous remote work-friendly vacation rentals available, totaling around 97 options. Many of these properties offer essential amenities for working remotely, including reliable Wi-Fi, dedicated office spaces, and comfortable desk setups. Travelers can expect accommodations that feature desks, desk chairs, and laptop workspaces, making it easy to balance work and leisure during their stay.

Cupar itself is a charming town with a rich history, providing a peaceful atmosphere for productivity. The area is surrounded by beautiful countryside, ideal for relaxing after a day of work. Additionally, local cafes and shops are within reach, offering opportunities for breaks and refreshments. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cupar vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cupar with parking available—perfect for families or travelers 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 include WiFi, kitchens equipped for cooking, and electric kettles for convenient tea and coffee preparation. Many properties also permit pets, accommodating travelers who wish to bring their furry friends along. Additionally, service animals are allowed, ensuring that guests with specific needs can feel comfortable during their stay.
When is the best time to visit Cupar for a vacation rental?
September is the most popular time to visit Cupar, as it marks the transition from the bustling summer months into a period of milder weather and fewer crowds. The peak season runs from July to September, attracting travelers interested in exploring the charming landscapes and historical sites of this picturesque Scottish town. During these months, visitors can comfortably partake in outdoor activities such as hiking and sightseeing, with temperatures typically ranging from the mid-50s to low 70s Fahrenheit.

In September, the climate is generally pleasant, providing the ideal backdrop for leisurely strolls through the local parks or enjoying a round of golf at the nearby courses. The beautiful autumn colors begin to emerge, adding a touch of magic to Cupar's already stunning scenery. This month also offers a more relaxed atmosphere, allowing visitors to savor cultural experiences without the summer rush.

For those looking to save some money, December is considered the low season for visiting Cupar. While the winter months can be chilly, this time of year provides a unique opportunity to experience the town's festive charm, including holiday markets and local celebrations.

Ultimately, the best time to book a vacation rental in Cupar depends on your preferences.
How early should I book a Cupar vacation rental?
Book your Cupar vacation 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 vacation 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 enjoy a charming blend of historical and natural attractions. The town's centerpiece is the historic Cupar Castle, which offers insights into the area's rich heritage. Nearby, the lovely Cupar Golf Club provides scenic views and a relaxing atmosphere for golf enthusiasts. For those interested in nature, the picturesque Lomond Hills Regional Park is just a short drive away, offering excellent hiking trails and stunning landscapes. Additionally, the town is known for its traditional Scottish architecture, with quaint shops and cafes lining the streets, creating a delightful local experience.
Can I change or cancel my Cupar home rental booking on Vrbo?
To find Cupar vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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