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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Top guest favourite
The exterior of the cottage is showcased, featuring a stone facade with a tiled roof. Windows reflect bright daylight, framing a well-maintained garden with green grass and blooming shrubs. A pathway leads to the entrance, highlighting a welcoming approach to the home.
Cottage in Ceres
4.96 out of 5 average rating, 236 reviews

Homely cottage & tranquil garden, beaches nearby

Penny Cottage is a beautiful, homely old weaver's cottage from 1783, with original features and a peaceful, secure garden, great for dogs. Space is perfect for 2–3, cosy for 4. Perfectly situated for exploring Fife's beaches, countryside, golf courses and historic settlements. Ceres is one of Scotland's 'Most Attractive Villages' with a shop, pub and cafes. St Andrews and Cupar nearby. NO wifi available. Airbnb policy - booking to be made by person staying at the property. Licence no: FI-00488-F

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, 134 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 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, 172 reviews

Lovely top floor flat 3 bedrooms & private parking

This is a great central flat in Cupar with the train station just a 2 minute walk away, and the taxi rank even closer, and only a 15-minute drive to St Andrew's with some amazing golf venues, ideal for a getaway, golfing trip or just to explore Scotland With speakers built into the roof it is ideal for a nice relaxing time away. And a train running to Edinburgh and Dundee every hour a vehicle will not be needed. However, Private parking is included so there is no worry about paying any meters.

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, 166 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
Apartment in Falkland
4.96 out of 5 average rating, 158 reviews

The Studio at Old Lathrisk

The Studio at Old Lathrisk (FI 00782 F) is a ground floor apartment in a 16th century Scottish country house near Falkland (where the series #Outlander is filmed!). It's a beautiful, stylish, cosy holiday space for 2 with an ensuite shower room and self catering cooking facilities. A perfect romantic hideaway with doorstep parking, a private entrance and access to the family's large beautiful garden. The countryside apartment is set in mature parkland with a beech lined driveway to the house.

Top 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, 285 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
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, 255 reviews

Braeview: Cosy studio farm cottage near St Andrews

We have lovingly converted a 200 year old cartshed 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 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, 156 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 charming exterior view of the Woodside Retreat features a large window with multiple panes, surrounded by smooth stone walls. Two potted plants sit beneath the window, adding greenery to the entrance. A brick pathway leads to the property, creating an inviting approach.
Cottage in Fowlis
4.95 out of 5 average rating, 240 reviews

Woodside Retreat with Garden

Woodside Retreat is in a fantastic relaxing village location! It is a lovely, newly furbished, fresh, bright property with a private garden nestled beside woodland and located in the countryside. It is the perfect place to relax and recharge or explore and enjoy the areas nearby. Situated in Scotland near to Piperdam Golf Course, Dundee, and within easy travelling distance of Edinburgh, St Andrews, Dunkeld, Perthshire. We are dog friendly and can accommodate one house trained dog.

Top guest favourite
An outdoor sitting area features two wooden chairs painted in a soft green hue, complemented by a hanging flower basket filled with vibrant blooms. A small garden with various plants and flowers enhances the rustic charm, surrounded by gravel and a wooden fence.
Guesthouse in Angus Council
4.96 out of 5 average rating, 203 reviews

"The Wee Bothy" - Studio Annex - near Arbroath.

The “Wee Bothy” offers a great base to explore the North East Coast, our scenic Angus Glens, and nearby Towns and Cities with places of interest all around. The Seaside/Harbour town of Arbroath is a 5 min drive away, with lots of lovely Cafes, Restaurants, Cinema and Theatre. Golfing, Fishing , Kayaking round the Cliffs and Walking, are plentiful in and around the area with Carnoustie Golf Links a 15 minute drive. Bus and Train Station in town for those who want to venture further.

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.
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 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, 102 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.

Popular amenities for Cupar vacation rentals

When is the best time to visit Cupar?

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Avg. price$199 CAD$183 CAD$192 CAD$168 CAD$199 CAD$202 CAD$217 CAD$230 CAD$182 CAD$172 CAD$196 CAD$221 CAD
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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 apartment rentals in Cupar have wifi?

    Absolutely! We offer over 10 apartment 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 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.

  • Where should I stay in Cupar?

    Make yourself at home in Cupar by choosing from our most frequently booked neighborhoods. We have over 140 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 $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,760 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

    40 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