Family-friendly holiday rentals in Cupar

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Top-rated family-friendly rentals in Cupar

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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 Peat Inn
4.99 out of 5 average rating, 214 reviews

Eastburn: Gorgeous 2-bed cottage near St Andrews

Eastburn Cottage was created from our lovingly converted 200 year old cartshed. 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 (the one on the right) 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.

Top 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, 135 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, 167 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 Howff' is showcased, featuring a quaint structure with a grey stone finish and a chimney. Surrounding lush greenery and rolling hills provide a natural backdrop. A small garden area with flowering plants is visible, enhancing the rural ambiance.
Tiny home in Balbeggie
4.99 out of 5 average rating, 180 reviews

Writer's Retreat in the heart of Perthshire

'The Howff' is a refurbished farm worker's bothy in a rural location with lots of walks and access to beautiful parts of Perthshire. One hour's drive from Edinburgh, 20 mins Dundee or Perth. This authentic bothy contains one room with single bed, wood burning stove, mini kitchen unit with fridge, oven, portable hob and kettle, separate shower room, wc, basin. Linen and towels included. Although small, The Howff is warm and cosy and makes a perfect retreat. Please note for ONE only.

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, 162 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 panoramic view of Edinburgh highlights a blend of historic and modern architecture. The city is framed by lush greenery and rolling hills, with notable landmarks such as the castle and church spires visible against a vibrant sky.
Townhouse in Stockbridge
4.94 out of 5 average rating, 180 reviews

Private suite in Gorgeous Georgian house

King Sized bedroom with own en suite bathroom in a beautiful Georgian four storey town house on a picturesque garden square in the UNESCO World Heritage New Town. This freshly renovated basement flat has its own private front door. The house is in the Stockbridge area of Edinburgh, close to the city centre, minutes away from fabulous artisan cafes, fantastic restaurants, delis, bars, independent shops and galleries. Across the square is Glenogle Baths with a gym, sauna and swimming pool.

Top Guest favourite
The exterior of a charming yellow cottage is depicted, featuring a red-tiled roof and multiple small windows adorned with flower boxes. A white door is positioned at the center, surrounded by a cobbled courtyard with greenery, creating a tranquil setting.
Cottage in Fife
4.99 out of 5 average rating, 248 reviews

The Burghers Kirk @ 136, St Andrews

The Burghers Kirk is a quaint 1 bedroom cottage full of character and quirky features with a secluded courtyard garden and is situated in the heart of St Andrews, close to the West Port and the medieval core of the town. Recently refurbished to a contemporary and high standard the cottage is suitable for 2 adults. Originally built in 1749 and used by the Burgher Kirk congregation, it was gifted to the St Andrews Preservation Trust in 1954 and reconstructed into a charming cottage.

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, 115 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, 106 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
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, 106 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
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
4.94 out of 5 average rating, 155 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 fantastic food all day; the Hayloft and Pillars of Hercules are lovely cafes. Fine dining at the Boar's Head in nearby Auchtermuchty.

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.July-Sept rate cuts

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 family-friendly rentals

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 $192 NZD per night before taxes and fees

  • Verified guest reviews

    Over 940 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Cupar holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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