Vacation rentals in Cupar

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Top-rated vacation 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 🙂

Top guest favourite
Cottage in Falkland
4.94 out of 5 average rating, 179 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
The charming stone building features a dark front door framed by two windows with flower boxes, each containing pink flowers. A small set of steps leads to the entrance, contributing to the inviting facade.
Condo 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
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.

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, 324 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
A spacious living area features a large corner sofa with various cushions, positioned in front of a stone fireplace. Natural light floods the room through skylights and glass walls, revealing views of the surrounding landscape and an outdoor seating area.
Guest suite in Brunton
4.99 out of 5 average rating, 76 reviews

Brunton Hill

Come and be rejuvenated in our beautiful, peaceful space - relaxing (luxuriously) in nature, with expansive views, leaving all your cares behind. Brunton Hill can offer you a quiet and very comfortable space to retreat, exploring the very local scenery, walking the dog or on bikes; or, as a base from which to visit St Andrews (16 miles) , Fife Coast and beaches, Dundee and the V&A (12 miles), Southern Cairngorms and Perthshire. For a bird’s eye view look up Brunton Hill Retreat on YouTube.

Top guest favourite
The exterior of a contemporary barn conversion showcases a spacious gravel driveway flanked by lush greenery and seasonal flowers. Large windows reflect natural light, while solar panels indicate sustainability. The structure's rustic stone facade contrasts with the modern elements, all set against a cloudy sky.
Condo 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
Cottage in Fife
5 out of 5 average rating, 232 reviews

Luxury one-bedroom cottage ŵ outdoor bath & views

This unique cottage has a style all of its own with beautiful views over the fields to the sea. Sit and relax in peace and luxury or in the outdoor woodfire hikki bath. All newly renovated and fully equipped to be your home away from home. Centrally located just 40 from Edinburgh, St Andrews, Gleneagles and Elie and only 10 minutes from local villages, all with links to local transport. Plus 30 minutes from Edinburgh airport. However once here we guarantee that you won't want to leave.

Guest favourite
Cottage in Blebocraigs
4.98 out of 5 average rating, 117 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
The kitchen showcases a modern design with exposed brick accents and ample cabinetry. Skylights provide natural light, highlighting the stainless steel appliances, including a kettle and coffee maker. A wooden dining table with four stools is positioned nearby, offering a casual dining space.
Apartment in Fife
4.98 out of 5 average rating, 124 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 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, 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.

Superhost
A comfortable sleeping area is presented with a spacious bed featuring a tufted headboard. Two bedside tables with decorative lamps frame the bed, which is adorned with a neutral blanket and a decorative animal pillow. A window with blinds and a small table beside it completes the setting.
Apartment in Fife
4.83 out of 5 average rating, 29 reviews

Southbridge Studio

2 bedroom Studio apartment in the centre of the idyllic town of Cupar. This property is pet friendly. Ideal for families, Contractors and Tourists alike. Southbridge Studio is in close proximity to high street shops, restaurants, pubs and train station. There are plenty of walks in Cupar for those who love nature and for the golf enthusiasts, Fife boasts some of the best courses in Scotland.

Popular amenities for Cupar vacation 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 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 vacation rentals in Cupar

  • Total vacation rentals

    Explore 40 vacation rentals in Cupar

  • Nightly prices starting at

    Cupar vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,550 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Cupar vacation 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!

  1. Airbnb
  2. United Kingdom
  3. Scotland
  4. Fife
  5. Cupar