Cupar holiday homes

We found 1,457 holiday rentals — enter your dates for availability
Select from 33 homes, 76 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:30 Oct - 6 Nov

Image gallery for A delightful and historic property just a few steps from the harbour.

Harbour, only a few steps away
10 out of 10, Exceptional, (88 reviews)
Exceptional
(88 reviews)

A delightful and historic property just a few steps from the harbour.

Anstruther

6% off
Price is NZ$3,765
for 7 nights, 1 cottage
NZ$538 per night
includes taxes & fees
A delightful and historic property just a few steps from the harbour.

Find spaces that suit your style

  • 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

Why visit Cupar

  • Historic charm: Cupar boasts a rich cultural heritage with its iconic castle and well-preserved historic streets.
  • Urban oasis: Enjoy a tranquil urban park perfect for leisurely strolls and family picnics.
  • Coastal escapes: Embrace the scenic beauty of nearby beach spots for outdoor adventures and relaxation.
  • Welcoming community: Experience the friendly local atmosphere that makes exploring Cupar a delight.
  • Family-friendly exploration: Discover a mix of history and nature ideal for romantic getaways or family excursions.

Top attractions near Cupar

Experience the charm of Cupar, Scotland, a city that offers a blend of rich culture and outdoor adventure. Discover its historic castle, urban park, and nearby beach spots perfect for a scenic getaway. Ideal for travellers seeking a mix of cultural exploration and outdoor fun, Cupar provides a unique backdrop for those who appreciate both history and nature.

  • St. Andrew's Castle: Experience a romantic ambience at this historic castle known for its rich culture, located 14km from Cupar.
  • Elie Beach: Enjoy a classic beach vibe with sandy shores and refreshing sea air, situated 18km from Cupar.
  • St Monans Heritage Collection: Delve into local culture at this museum, offering insights into regional heritage, positioned 19km from Cupar.

Things to do recommended for couples

Experience Cupar like never before. Enjoy hand-in-hand strolls through historic streets, a cosy picnic by the loch, and intimate local dining for a memorable escape. Perfect for a couple's retreat.

Things to do recommended for families

Families can explore the scenic beauty of Cupar, from its historic landmarks to local parks perfect for picnics and strolls, while enjoying a relaxed pace that reflects New Zealand's love for the outdoors.

Things to do recommended for groups

Group travellers in Cupar can enjoy a local experience by exploring historic landmarks, sampling traditional Scottish cuisine, and engaging in community events, all while appreciating the scenic countryside and vibrant culture that characterises the area.

*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

When planning your trip—whether you're travelling with friends, family, pets, or seeking extended stays—it's essential to prioritise your preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Cupar with a group: Consider how many bedrooms you'll require, along with features like a fully equipped kitchen or an outdoor area suitable for group gatherings. Luckily, you can use filters on Vrbo to find exactly these, and even more.
  • Traveling to Cupar with young kids: Traveling with young kids can be a challenge. You must ensure their comfort and safety, along with suitable facilities like a private swimming pool. It’s also wise to consider how close you are to attractions that are family-friendly.
  • Taking your pets with you to Cupar: For many, a family holiday wouldn’t be complete without their four-legged companion. If that’s you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer feeding bowls and beds so everyone can feel right at home.
  • Planning for a long term stay visiting Cupar: If you’re after holiday rentals that offer deals for monthly stays, you’ve come to the right spot. With the proper filter, you can effortlessly find and save on long-term rentals. You might also like to include options such as secure parking, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Cupar

Cupar, Scotland, offers a delightful blend of adventure and history for visitors. Explore its charming streets, where friendly locals create a welcoming atmosphere. Enjoy outdoor activities in tranquil settings, perfect for a romantic getaway or a family-friendly excursion. Discover the rich heritage of this historic town, with its scenic landscapes and engaging experiences waiting to be uncovered. Cupar promises a memorable stay filled with relaxation and exploration.

  • Falkland: Nestled in the heart of the Cupar area, Falkland is a charming village known for its rich historic ambiance and scenic outdoor adventures. Visitors can immerse themselves in culture-themed experiences and explore the local shopping area, ideal for uncovering unique treasures. The expansive hiking trail and trail access offer ample opportunities for adventure enthusiasts to enjoy the great outdoors. Historic places, a castle and a monument add to the village’s allure, making it a perfect destination for travellers seeking a blend of history, culture, and outdoor escapades.
  • Freuchie: Located near Cupar, the village of Freuchie is a haven for those who appreciate outdoor beauty and scenic landscapes. Ideal for adventure seekers, the area offers a range of activities from leisurely strolls in recreational areas to a challenging round of golf on a well-maintained course. The proximity to a national park and national state park provides the perfect backdrop for nature walks, while a nearby hill offers breathtaking views of the surrounding countryside. Freuchie is a destination that seamlessly blends natural beauty with opportunities for active exploration.
  • Ceres: Just a short journey from Cupar, Ceres is a delightful village that caters to families and adventure enthusiasts alike. Outdoor activities abound, with trail access and a well-loved hiking trail encouraging exploration of the scenic surroundings. A popular golf course invites both novices and seasoned golfers to enjoy a round in a picturesque setting. Local attractions such as a botanical garden, park, and lake provide diverse opportunities for relaxation and leisure, making Ceres an excellent choice for a well-rounded holiday experience.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January39.0°F (3.9°C)Light RainMostly CloudyAverage
February39.9°F (4.4°C)Light RainMostly CloudySlightly High
March41.9°F (5.5°C)Light RainMostly CloudyAverage
April45.0°F (7.2°C)No Rain (Dry)Mostly SunnyAverage
May49.6°F (9.8°C)Light RainMostly CloudySlightly Low
June54.5°F (12.5°C)Light RainMostly CloudyAverage
July57.9°F (14.4°C)Light RainMostly CloudySlightly High
August57.6°F (14.2°C)Light RainMostly CloudyAverage
September54.5°F (12.5°C)Light RainMostly CloudySlightly High
October49.8°F (9.9°C)Light RainMostly CloudySlightly Low
November44.2°F (6.8°C)Light RainMostly CloudyAverage
December40.3°F (4.6°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Looking to cut costs on your next getaway? Being flexible with your travel dates can really pay off, as prices often fluctuate. You might also enjoy great savings by choosing an extended stay. To find a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your existing arrangements, or review your bookings. Your saved and booked properties are neatly organised into categories: Potential, Upcoming, or Current Trips. To discover more about Trip Boards, head over to: https://www.bookabach.co.nz/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)
  • St Andrews - Jubilee Course (7.9 mi / 12.8 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)

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)
  • 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)

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 home?
Ceres is one of the most popular locations to get a holiday home in Cupar. Have a look at our selection of comfy stays and then get out and discover this destination like a local.
What is the most popular type of holiday home accommodation in Cupar?
Based on our data, cottages are the most desirable type of holiday property in Cupar. But as you'd expect, everyone's idea of an awesome stay is bound to be different. Bookabach has holiday homes of all sizes, shapes and budgets, and we'll help you discover your ideal match.
How much does it cost to rent a holiday home in Cupar?
A number of factors can determine what you'll pay for your holiday home in Cupar, including the season, length of stay and type of property. However, all of our holiday homes have one thing in common — exceptional value. Just enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Cupar?
Prices for beach houses in Cupar may differ depending on the size and type of the property and when you plan to travel. All you need to do is enter your travel dates into Bookabach and how many guests to view your home options and prices. From there you can use our filters to narrow your search results by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday homes in Cupar?
Pack a bone and a squeezy toy for the pooch in your life because Cupar has 92 properties that throw out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly holiday homes on Bookabach. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.
What are popular home amenities in Cupar?
An electric car charging station, a nearby river and a fireplace top the list of most popular home amenities in Cupar. Whether you're taking to the road as a party of one, with your better half or a group of best friends, Bookabach can help you find a holiday home that matches your style with all the conveniences you're looking for.
Are there large group holiday homes in Cupar?
Cupar has four holiday homes that can accommodate 10 or more guests. These stays come with the privacy and space you need to share good times with loved ones.
Are there holiday homes in Cupar that welcome kids?
Bring the whole group together for fun-filled adventures in Cupar at one of our 91 family-friendly holiday homes. Many of these stays come with amenities that are ideal for trips with youngsters, like laundries, multiple bedrooms and private pools. Simply click on the "Properties good for families" filter and decide on your favourite.
What are the top attractions for families in Cupar?
There are plenty of cool things to do and see with the family in Cupar, such as:

  • St. Andrews Castle
  • Falkland Palace
  • Leven Beach

Are there one-bedroom holiday homes in Cupar?
You'll find 27 one-bedroom properties in Cupar to choose from. A one-bedroom holiday home is a great option if it's just you and your partner or if you're travelling on your own. Throw in more privacy, convenience and space compared to a standard hotel, and you've got the makings of a getaway to remember.
Can I find two-bedroom holiday homes in Cupar?
Choose from 36 two-bedroom holiday homes in Cupar. Put the kids in the second room or maybe fill it with a couple of your favourite people. There's ample space for whoever's lucky enough to be coming along.
Are there holiday homes with WiFi in Cupar?
Whether you'd like to keep up to date with the news, check emails or surf social media, there are 15 holiday homes with WiFi in Cupar. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Cupar?
You'll have your pick of two holiday homes with air conditioning in Cupar offering that cooling breeze and extra touch of comfort. Enter your preferred dates of travel and then use our handy filter tool to help you find stays with air conditioning.
How old do you have to be to rent a holiday home in Cupar?
The minimum required age is generally 16, 18 or 21. It can change between properties on Bookabach, so look at the rules of your chosen Cupar stay before you book.
How long can I rent a holiday home in Cupar for?
The amount of time you can stay in a Cupar holiday home for varies depending on the property. Just put in your preferred travel dates to see options offering extended stays. They feature all the things you need to make your extended holiday more enjoyable and comfortable, like kitchens and yards. Some properties might also offer weekly or monthly discounts, so you can stick around for longer for less.

More holiday ideas