Holiday rentals in Cupar

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Top-rated holiday rentals in Cupar

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
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
4.94 out of 5 average rating, 248 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.

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.
Apartment
4.99 out of 5 average rating, 139 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
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.

Top guest favourite
The exterior of The Old Pump House is showcased, featuring a large wooden deck with steps leading up to it. Two wooden chairs and a small table are positioned on the deck, while a gas BBQ is visible nearby. Lush green trees provide a natural backdrop.
Tiny home
4.97 out of 5 average rating, 557 reviews

Restored Pump House - 6 miles from Perth

This unique dwelling was originally a water pumping house for the local village and was restored in 2020. Just 6 miles from Perth, this tiny house offers access to miles of glorious Perthshire countryside. With plenty of private parking, quirky ladder to the mezzanine sleeping area, wood burner, underfloor heating plus modern fixtures and fittings, The Old Pump House offers the perfect accommodation for lovers of the great outdoors. P&K License Number - PK11501F EPC rating - Band D (67)

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.
Apartment
4.99 out of 5 average rating, 174 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
The exterior of the tiny house features traditional stone walls and a sloping roof. A blue door serves as the entrance, framed by two white windows. The cobblestone path leads to a small, manicured grassy area, with warm light reflecting off the building during sunset.
Tiny home
4.99 out of 5 average rating, 125 reviews

Tiny House in Cosy Village

Dating back to the 1700s, this tiny house had sat empty for over 50 years until George (Heather's son) invested his life savings to completely renovate it to a high standard, while retaining the original character of the building. Sitting below Bishop Hill in the picturesque village of Kinnesswood (2023 joint winner of Britain in Bloom's 'Village' category!), the tiny house is surrounded by breathtaking views, fantastic walks, and an abundance of local farm shops, cafes, and restaurants.

Guest favourite
An open plan living area features a round wooden dining table surrounded by four black chairs. Two red and gray striped armchairs are positioned nearby, next to a wooden cabinet. Natural light enters through two large windows with beige curtains, while a stone wall adds character.
Cottage
4.98 out of 5 average rating, 118 reviews

Clatto Bothy, self catering cottage.

Clatto Bothy is a recently refurbished, fully furnished semi-detached cottage less than five miles from St Andrews. The self catering accommodation consists of a spacious open plan kitchen and dining area and a large living space. There is one double bedroom and a large shower room. The cottage sleeps two and offers peaceful surroundings within easy reach of St Andrews. The kitchen is fully equipped including washing machine and dishwasher. The Bothy has its own private parking area.

Top guest favourite
A cozy living space features a soft gray sofa and armchair, complemented by natural decor elements. A wood accent shelf holds a basket and plaid throw, while a lamp stands beside a textured side table. Light enters through an open door, illuminating the room.
Cottage
4.98 out of 5 average rating, 257 reviews

Escape to a luxury country cottage and ocean views

Built in 1829 Drinkbetween East has had a complete renovation and make over. Every detail has been thoughtfully selected to ensure the most comfortable and luxurious stay possible. The cottage is ideally located on Banchory Farm a 40 minute drive from Edinburgh, St Andrews and Gleneagles with easy access to public transport links. With your own private garden and fire pit enjoy the peacefulness and calm that beautiful rural Scotland has to offer so you can truly relax and unwind.

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.
Flat
4.98 out of 5 average rating, 125 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
An inviting loft space features exposed wooden beams and a warm color palette. Comfortable seating arrangements include a plush sofa and armchairs placed around a rustic wooden coffee table. A stylish lamp illuminates the area, enhancing the cozy ambiance.
Flat
5 out of 5 average rating, 113 reviews

Ord’s Loft - Old Town Historic Apartment

Ord’s Loft, situated in White Horse Close, is one of the most desirable and unique properties in Edinburgh’s old town. Positioned on the top floor of what was once the White Horse Coaching Inn, built by Laurence Ord in 1624, the loft is entered by the iconic steps seen in so many photos of Edinburgh. The outlook south over the courtyard is Holyrood Palace, Arthurs Seat, the Scottish Parliament and the Old Town while to the rear it looks up to Regent Road and Calton Hill.

Top guest favourite
A charming entrance is visible with a set of stairs leading to a Shepards hut, surrounded by greenery. Potted plants and a small wooden table with two folding chairs create a welcoming outdoor space for relaxation.
Shepherd’s hut
4.97 out of 5 average rating, 129 reviews

Cosy heated Shepard’s hut with beautiful views

A very comfortable, heated, beautifully appointed Shepards hut with stunning views over the Tay valley. An ideal location to relax, reconnect and explore the magic of Perthshire. We have ancient Caledonian woodlands for you to explore, full of incredible wildlife and a wild swimming pond for those looking for a cold water fix - look us up under cotwild The Shepards hut sleeps 2 adults & 2 children under 12yrs on a sofa bed sleeping bag. 2 well behaved dogs welcome.

Top guest favourite
Castle
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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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Cupar?

    Cupar has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Cupar with our house rentals, starting at about $60 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 vacation rentals in Cupar?

    Four-legged friends are welcome in Cupar. Choose from more than 20 vacation 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 apartment rentals in Cupar have wifi?

    Absolutely! We offer over 10 apartment 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 €17 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Cupar holiday rentals include wifi 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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  2. United Kingdom
  3. Scotland
  4. Fife
  5. Cupar