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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Guest favourite
A distinctive black entrance door features two large panels and a smaller window above. The door is marked with the number '30' and has a small doormat with a heart design placed at the base. Surrounding stonework displays various textures.
Home in Fife
4.94 out of 5 average rating, 16 reviews

Number•30•

4 bedroom property (sleeps 8 guests) located in Cupar town centre, with all essential facilities, amenities and transport links within a short walking distance. This unique building is full of character, and offers a bright and spacious stay for guests. The private entrance door is located to the front with a private courtyard to the rear. Free car parking is available in nearby car parks. 2 guests are welcome to book the lower floor (double bed room) at a discounted price, please just ask 🙂

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, 240 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 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
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, 321 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 inviting entrance leads to the cottage, featuring patio doors that open to the garden. Colorful flowers border a stone pathway, while a cozy seating area is positioned near the entrance. A small wooden sign and garden furniture complement the serene outdoor space.
Guest house in Fife
4.94 out of 5 average rating, 217 reviews

Self-contained cottage, 2 miles from St Andrews.

Self contained wee cottage. Living room with feature stone wall, fully equipped kitchen and patio doors opening onto the garden. Best suited for a couple with 1 double bed in the ensuite bedroom. Chair-bed suitable for child or small adult for £20 extra. Well-behaved pets welcome but NOT to be left on their own, garden is enclosed but not secure. No weeing or soiling on the grass. Complimentary breakfast for the first morning, plus tea, coffee and condiments Wifi strong STRICTLY NO SMOKING

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 in Methven
4.97 out of 5 average rating, 548 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 in Fife
4.99 out of 5 average rating, 172 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.

Guest favourite
Cottage in Blebocraigs
4.98 out of 5 average rating, 115 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 in Fife
4.98 out of 5 average rating, 256 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.
Flat 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, 213 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.

Top 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, 113 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.

Popular amenities for Cupar holiday rentals

When is the best time to visit Cupar?

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Avg. price$184 SGD$165 SGD$165 SGD$152 SGD$181 SGD$183 SGD$197 SGD$209 SGD$165 SGD$169 SGD$158 SGD$161 SGD
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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 $26 SGD 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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  5. Cupar