Holiday houses in Cupar

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Top-rated holiday rentals in Cupar

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Guest favourite
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
4.94 out of 5 average rating, 231 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
A traditional terraced cottage is set against a lush green hillside under a partly cloudy sky. A red-tiled roof contrasts with stone walls. Flower pots are placed near the entrance, enhancing the cottage's rustic charm. The spacious surrounding landscape invites exploration.
Cottage in Falkland
4.93 out of 5 average rating, 169 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, 137 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.

Top 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, 311 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
An open plan kitchen and dining area features a rustic wooden table surrounded by black chairs, positioned beside a large window with a view. Navy cabinetry complements the stainless steel appliances, while white walls and elegant light fixtures enhance the space's brightness.
Cottage in Newburgh
5 out of 5 average rating, 126 reviews

Luxury River View Farm Cottage + Dog Friendly

Enjoy stunning views over the River Tay from a luxury countryside base (35 mins to St Andrews & 50 mins to Edinburgh). Old Parkhill at Hyrneside is a beautifully restored 3 bed farm cottage, featuring a stylish open plan space, designer kitchen, wood stove and heated polished concrete floors. Relax in marble washrooms, one with a clawfoot bath, the other a walk-in shower. French doors open out to a courtyard dining area + pizza oven, fire pit and acres of farmland, forest + trails to explore.

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 Dairsie
4.99 out of 5 average rating, 170 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
A spacious living area is highlighted by a comfortable brown leather sofa and a large ottoman. A television is positioned against the wall, while a soft glow is provided by a lamp beside a fireplace. Light enters through the window, complementing neutral wall tones.
Home in Fife
4.95 out of 5 average rating, 119 reviews

Balass Lodge near The Old Course St. Andrews

Luxury country home 10min drive from the historic golfing town of St. Andrews and 1hr 20min from the stunning Cairgorms. Three bedrooms contain super king sized beds which can also be split into singles - one with an ensuite bathroom, the other two share a large main bathroom. The fourth bedroom has a king sized double bed and an ensuite shower room. The house has a games room with a pool table, smart TVs with full Sky HD, as well as a wood burning stove and a hot-tub on the terrace.

Top Guest favourite
The exterior view of the detached annexe is surrounded by lush greenery and mature trees, including two prominent apple trees. A well-maintained lawn stretches across the area, creating a serene countryside setting under a clear blue sky.
Holiday home in Rathillet
5 out of 5 average rating, 110 reviews

Detached Country Annexe 20 mins from St Andrews

Welcome to our recently converted 1 bedroom detached annexe. Apple View is a no smoking property. It occupies a delightful countryside location with rolling views to the Lomand Hills whilst also having easy access by car to the many nearby attractions of St Andrews Cupar,Falkland,Perth.Dundee and Edinburgh. Whether it is country walks, beaches, historic houses and gardens, golf, museums, or city attractions there really is something for everyone in this wonderful part of Scotland.

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 in Fife
4.98 out of 5 average rating, 252 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.

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, 115 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.

Guest favourite
The traditional stone cottage stands amidst lush greenery, featuring a charming black front door and symmetrical windows. The sloping roof and elegant dormer windows enhance its character. A well-maintained lawn extends in front, providing a welcoming outdoor space.
Cottage in Cupar
4.91 out of 5 average rating, 109 reviews

Garden Cottage, nr St Andrews. Spring - new rates!

Garden Cottage is a traditional 2 bedroom cottage with central heating, free wi-fi and its own garden, & access to our tennis court. Located on our private country estate about 9 miles from St Andrews. Price includes bed linen, towels, wi-fi & electricity, starter pack of coal, & logs for the fire. Sleeps 4 adults + child/baby, in 1 double bed, 2 single beds & futon. Cot provided. EV charger. STL licence no. FI-00612-F, by Fife Council. Sorry, no pets.

Guest favourite
The kitchen features modern cabinetry with a light finish, complemented by a wooden countertop. A built-in oven and stovetop are prominently displayed. Natural light floods the space through large windows, highlighting the neutral tile floor and providing a bright cooking environment.
Condo in Fife
4.9 out of 5 average rating, 177 reviews

Lovely top floor flat 3 bedrooms & private parking

This centrally located flat in Cupar is just a 2-minute walk from the train station, with the taxi rank even closer. St Andrews is only a 15-minute drive away, making it ideal for a golfing trip, relaxing getaway, or exploring Scotland. The flat features built-in ceiling speakers for a comfortable, relaxing stay. Trains run hourly to Edinburgh and Dundee, so a car isn’t essential, though private parking is included for added convenience.

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 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 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 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 150 vacation rentals in Cupar, and over 70 vacation rentals in Cupar Muir.

  • Do apartment rentals in Cupar have a kitchen?

    Absolutely! We offer over 10 apartment 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 1,850 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

    40 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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  5. Cupar