Vacation rentals in Cupar

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Top-rated vacation rentals in Cupar

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Guest favorite
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, 158 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.

Top guest favorite
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 favorite
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.

Guest favorite
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.
Guesthouse in St Andrews
4.94 out of 5 average rating, 213 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 favorite
The cottage features a stone exterior with a red-tiled roof, complemented by large glass doors opening to the garden. A well-maintained lawn surrounds the structure, with a solitary tree positioned nearby against a bright blue sky, creating a peaceful outdoor setting.
Cottage in Peat Inn
4.99 out of 5 average rating, 262 reviews

Braeview: Cosy studio farm cottage near St Andrews

We have lovingly converted a 200 year old cart shed into 2 cottages. Braeview Cottage at Braeside Farm is a spacious studio space with a king size bed on the mezzanine floor. Downstairs next to a modern kitchen you have an open area with large french doors to a patio with a great view across the brae. On a farm set in 13 acres and 500 m from the nearest road, you will savour the tranquillity yet it's a 10 to 15 min drive to St Andrews and an hour from Edinburgh Airport. A car is required.

Top guest favorite
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, 182 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 favorite
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 favorite
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 favorite
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.
Vacation 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 favorite
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, 108 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 favorite
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.

Guest favorite
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, 174 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 vacation rentals

When is the best time to visit Cupar?

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Frequently Asked Questions

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

Quick stats about vacation rentals in Cupar

  • Total vacation rentals

    Explore 40 vacation rentals in Cupar

  • Nightly prices starting at

    Cupar vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 1,850 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Cupar vacation 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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  2. United Kingdom
  3. Scotland
  4. Fife
  5. Cupar