Holiday houses in Cupar

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Top-rated holiday rentals in Cupar

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A round stone structure features a grand portico with an ornate archway and decorative details. Lush green grass surrounds the building, complemented by a backdrop of trees displaying autumn foliage. The clear blue sky adds brightness to the tranquil setting.
Tower in Edinburgh
4.93 out of 5 average rating, 246 reviews

Craigiehall Temple (historic property built 1759)

Make you trip to Edinburgh truly memorable with a stay at Craigiehall Temple. Built in 1759 and situated in its own grounds on a former part of the Craigiehall Estate, it's Grade A listed for its stunning portico displaying the arms of the 1st Marquess of Annandale. A plaque on the wall carries a quote from Horace: "Dum Iicet in rebus jucundis vive beatus", "Live happy while you can among joyful things". We hope that a stay at the Temple will deliver this experience and stay true to this vision.

Top Guest favourite
Cottage in Falkland
4.94 out of 5 average rating, 177 reviews

Beautiful royal-village cottage with wood-burner

Eastmost Cottage is in a wonderful position on the edge of the historic village of Falkland. It's a short walk from the fine Renaissance Falkland Palace, the heart of the medieval village with its independent shops, cafes restaurants and pub. There is great walking in the Lomond hills, accessible on foot. The wonderful Covenanter has great food all day; the Hayloft and Pillars of Hercules are lovely cafes. The Stag is a lovely bistro (our fav). Fine dining at the Boar's Head in Auchtermuchty.

Guest favourite
A charming two-story stone building features a dark front door with side windows. Flower boxes adorn the windowsills, while neatly trimmed bushes line the stone boundary. The facade displays a warm, inviting character, set along a quiet street.
Condo in Cupar
4.99 out of 5 average rating, 138 reviews

Luxury central ground floor flat (nr St Andrews)

Lovely 2 bedroom ground floor flat in the centre of Cupar, Fife. Private entrance. Outdoor enclosed seating area/courtyard (sun trap when weather is good). Quirky, cosy & comfortable. High quality kitchen & shower room. 20 min. drive to St Andrews, Dundee & East Neuk. Train station/buses less than 10 min. walk. Very central - one way quiet street. Supermarkets, Butcher, Baker, Post office, Chemist, Cafes, Take-away, Deli, Bars, Bistros and car parking all within a few minutes walk.

Guest favourite
An open-plan kitchen and living area features a circular kitchen island with seating. A ladder leads to a loft space, and natural light enters through a skylight and window. Warm wood flooring complements the decor, while a red accent curtain adds a touch of color.
Cottage in Fife
4.95 out of 5 average rating, 168 reviews

Romantic Cottage, nr St. Andrews with hot tub

Balass Hayshed Cottage finished to the highest standard and enjoyed by couples on mini moons, golf trips, weddings, visiting children at St Andrews University or just getting away from busy lives. The property has its own hot tub for the exclusive use of Hayshed guests only. There is a loft space with a further double bed. Enjoy the surrounding countryside. Edinburgh an hour by train. Dundee’s V and A 25 minutes. Rent along with the Stables Cottage for larger parties. Ultra fibre broadband.

Guest favourite
The open plan living area is characterized by double-height ceilings and large windows, allowing for ample natural light. A comfortable sofa is positioned next to a sleek coffee table. A stylish wooden staircase leads to the mezzanine, while modern art adorns the walls.
Barn in Fife
4.93 out of 5 average rating, 323 reviews

Beautifully converted farm barn with mezzanine

The Barn is a newly converted farm building on a quiet farm in a rural location 1km from Lundin Links. This 1 bed mezzanine is incredibly spacious yet cozy and welcoming. Finished & furnished to a high standard the property is well equipped with everything you will need to enjoy your stay. Fully contained garden to front, and private courtyard to rear, both ideally positioned to enjoy the morning and evening sun. Only a few minutes to the local beach, pub, shops & golf courses. Pets welcome.

Top Guest favourite
A secluded retreat is nestled among vibrant yellow fields, with lush green hills and a rocky peak in the background. The white structure is surrounded by trees, showcasing an inviting rural landscape under a partly cloudy sky.
Guest suite in Brunton
4.99 out of 5 average rating, 76 reviews

Brunton Hill

Come and be rejuvenated in our beautiful, peaceful space - relaxing (luxuriously) in nature, with expansive views, leaving all your cares behind. Brunton Hill can offer you a quiet and very comfortable space to retreat, exploring the very local scenery, walking the dog or on bikes; or, as a base from which to visit St Andrews (16 miles) , Fife Coast and beaches, Dundee and the V&A (12 miles), Southern Cairngorms and Perthshire. For a bird’s eye view look up Brunton Hill Retreat on YouTube.

Top Guest favourite
An open plan living area features high exposed wood beams and a cozy seating arrangement with a blue sofa and armchair. A wooden coffee table sits centrally, and light filters through double doors leading to the outside. A dining space and kitchen area are visible in the background.
Barn in Fife
5 out of 5 average rating, 83 reviews

The Roundel in Fife

Reconnect with nature at this unforgettable escape. ‘The Roundel’ near Cupar is a beautiful restored barn with its own private entrance. It offers a unique and private sanctuary for guests exploring the beautiful surrounding areas. This lovely open plan space forms part of what was once a traditional farm steading and sits in a quiet and peaceful setting. Guests also have use of a tennis court within the grounds. St Andrews, with its famous golf courses and beaches is just 20 mins by car.

Top Guest favourite
A gravel pathway leads through a landscaped area featuring colorful flowering plants and lush greenery along a stone wall. The buildings are visible in the background, showcasing a modern design with a gabled roof and large windows reflecting the outdoor scenery.
Condo in Fife
4.99 out of 5 average rating, 173 reviews

The Bothy; Cosy Country Hideaway near St Andrews

Welcome to The Bothy ! A recently renovated barn space forming a stunning 1 bed apartment enjoying spectacular views across local countryside. The property consists of a beautiful bedroom with superking bed (can also be set up as twin single beds) with views over a walled garden. The living area has a new kitchen and sitting room with woodburning stove. Located just 7 miles from St Andrews you can enjoy the tranquil location within easy reach of the historic town 10 minutes drive away.

Top Guest favourite
Cottage in Fife
5 out of 5 average rating, 231 reviews

Luxury one-bedroom cottage ŵ outdoor bath & views

This unique cottage has a style all of its own with beautiful views over the fields to the sea. Sit and relax in peace and luxury or in the outdoor woodfire hikki bath. All newly renovated and fully equipped to be your home away from home. Centrally located just 40 from Edinburgh, St Andrews, Gleneagles and Elie and only 10 minutes from local villages, all with links to local transport. Plus 30 minutes from Edinburgh airport. However once here we guarantee that you won't want to leave.

Guest favourite
A view from a window overlooks a vibrant street scene in Cupar, featuring a mix of traditional and modern buildings. The foreground reveals a corner store with a distinct sign, while the sky is dotted with clouds and sunlight, creating a lively atmosphere.
Townhouse in Fife
4.93 out of 5 average rating, 83 reviews

Number •6•

The 3 bedroom property (sleeps 6 guests) is located in Cupar town centre, with all essential facilities, transport links and amenities within a short walking distance. This traditional building is full of character, and offers a bright and spacious stay for guests. A private access door is located to the rear of the building, abundant free car parking is available. Cupar is located in North East Fife, only 9 miles from St Andrews, 13 miles from Dundee and 47 miles from Edinburgh.

Top Guest favourite
An airy open-plan kitchen and dining area features a wooden countertop, stove, and modern appliances. A cozy seating space with a sofa is illuminated by skylights. A decorative chandelier hangs above the area, and a small dog is seated by the dining table.
Apartment in Fife
4.98 out of 5 average rating, 123 reviews

Old Town Loft - stylish apartment

Set within the Conservation area of Cupar this chic apartment has a private entrance, 2 bedrooms, shower room, open lounge / dining / kitchen area and utility room. The property is tucked away along a lane with a pleasant old town aspect. Restaurants, cafes and shops are all nearby. There is a well appointed kitchen and dining table with 4 stools. Utility room with washing machine, drying and ironing. Towels, body wash, shampoo and conditioner provided. Up to 2 dogs welcome.

Top Guest favourite
Castle in Dollar
4.98 out of 5 average rating, 215 reviews

The Great Hall, Dollarbeg Castle

This 2 bedroom apartment is the beautifully converted former Great Hall of Dollarbeg Castle. Built in 1890, Dollarbeg Castle was the last gothic baronial style building of its type ever built. Beautifully restored in 2007 to the very highest standards, it was converted into 10 luxury properties, one of which is a conversion of the original "Great Hall" with its vaulted ceiling and majestic views across the formal grounds towards the Ochil Hills in the distance.

Popular amenities for Cupar holiday rentals

When is the best time to visit Cupar?

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Avg. price$202 AUD$181 AUD$181 AUD$167 AUD$198 AUD$201 AUD$216 AUD$229 AUD$181 AUD$185 AUD$173 AUD$177 AUD
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Frequently Asked Questions

  • Are there family-friendly house rentals in Cupar?

    Cupar has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Cupar?

    Experience the best of Cupar with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly apartment rentals in Cupar?

    Four-legged friends are welcome in Cupar. Choose from more than 10 apartment rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Cupar?

    Yes! Work meets play with ease at over 10 vacation rentals in Cupar featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Cupar?

    Make yourself at home in Cupar by choosing from our most frequently booked neighborhoods. We have over 160 vacation rentals in Cupar, and over 70 vacation rentals in Cupar Muir.

  • Do house rentals in Cupar have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Cupar. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cupar have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Cupar. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cupar have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Cupar. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Cupar

  • Total holiday rentals

    Explore 40 holiday rentals in Cupar

  • Nightly prices starting at

    Cupar holiday rentals start at $28 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,550 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Cupar holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cupar rentals

  • 4.8 Average rating

    Cupar stays are highly rated by guests—averaging 4.8 out of 5!

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  4. Fife
  5. Cupar