Family-friendly holiday rentals in Cupar

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Top-rated family-friendly rentals in Cupar

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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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.

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
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.

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, 130 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 charming stone cottage is set against a clear blue sky, surrounded by lush green lawns and trees. The building features large windows and a red roof, providing a welcoming appearance. The well-maintained grounds offer ample outdoor space for relaxation.
Cottage in Fife
4.99 out of 5 average rating, 226 reviews

Eastburn: Gorgeous 2-bed cottage near St Andrews

Eastburn Cottage was created from our lovingly converted 200 year old cart shed. On 13 acres of grounds accessed via a 400 metre track, Braeside Farm is tranquil yet a 10-15 minute drive to St Andrews and less than an hour from Edinburgh Airport. Eastburn is a 2 bedroom cottage with a kitchen and living room upstairs and a master bedroom (en suite) and smaller bedroom (with a triple bunk bed), bathroom and WC downstairs. Front door is at the top of the steps in the gable. A car is required.

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, 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
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
A wooden sign with elegant lettering displays the name 'Pitmeadow Farm'. It is set against a backdrop of greenery, with trees lining the path and grass suggesting a peaceful countryside setting.
Farm stay in Dunning
4.99 out of 5 average rating, 127 reviews

The Steading at Pitmeadow Farm

Pitmeadow Farm is situated in quiet countryside with lovely views. We are a small family run farm with pigs, ponies, sheep & chickens. The Steading forms part of our farm courtyard along with the farmhouse and our other holiday property (The Studio). Dunning (1 mile away) is a charming village with an excellent pub, local shop, golf course, tennis courts and a wide variety of walks. Ideal for exploring Scotland, visiting local attractions or just relaxing and recharging.

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.

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, 114 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.
Apartment in Fife
4.9 out of 5 average rating, 182 reviews

Stylish Cupar Flat | Near St Andrews | FreeParking

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 family-friendly rentals

When is the best time to visit Cupar?

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Avg. price$206 SGD$201 SGD$206 SGD$175 SGD$212 SGD$216 SGD$224 SGD$226 SGD$220 SGD$213 SGD$197 SGD$211 SGD
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Quick stats about holiday rentals that are family-friendly in Cupar

  • Total holiday rentals

    Explore 20 holiday rentals in Cupar

  • Nightly prices starting at

    Cupar holiday rentals start at $153 SGD per night before taxes and fees

  • Verified guest reviews

    Over 980 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Wifi availability

    20 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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