Vacation rentals in Cupar

4.9 out of 5 average rating, 132 reviews

Cabin in Craigrothie

Dream Tower Cabin

This uniquely designed cabin (co-created with architect Akiko Kobayashi) is a rural dream pad. Perfect for a quiet getaway, a romantic hideout or a base to explore the beauty of Fife. With a separate dedicated workspace it’s also a perfect place to write or create something special (or even to keep a hand in at work, not recommended!). The dynamic shapes of the building are designed to keep your eye satisfied and to encourage the curiosity required to be creative. 🏳️‍🌈 🏳️‍⚧️ LGBTQIA friendly

4.99 out of 5 average rating, 124 reviews

An inviting entrance is showcased with a double door, one side fully open to reveal a view of the street. A small decorative goat figure rests beside the door on the floor. The hallway features dark walls and framed artwork along the sides.

Condo in Cupar

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 less than 10 min. walk. Very central but in a 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.

4.98 out of 5 average rating, 184 reviews

The Waterfront

Overlooking the Tay estuary this stunning flat has views to take your breath away. A patio, a deck, and a quirky waterfront garden create an idyllic paradise. A luxe new shower room and stylish bedrooms create a unique holiday spot. Enjoy dinner on the deck or walk to excellent neighbouring restaurants. This newly launched flat from the 1860s is recently refurbished. It is close to Dundee and St Andrews and on the fife coastal path. A golfers paradise. An hour to the Cairngorms or Edinburgh.

A kitchen area is showcased, featuring a modern black sink and a drainboard. Large windows allow abundant natural light to stream in, highlighting a scenic view of the surroundings. A green plant sits on the windowsill, adding a touch of nature to the space.

4.89 out of 5 average rating, 143 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.

4.96 out of 5 average rating, 160 reviews

A snow-covered pathway leads to the cottage's stone façade, showcasing its rustic architecture. Large windows reflect winter sunlight, enhancing the warm tones of the building. The surrounding landscape is blanketed in snow, creating a serene and peaceful atmosphere.

Cottage in Fife

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.

4.96 out of 5 average rating, 221 reviews

Cottage in Ceres

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' - there is a shop, pub and coffee shops. St Andrews and Cupar are nearby. Airbnb policy - booking to be made by person staying at the property. Licence no: FI-00488-F

4.99 out of 5 average rating, 240 reviews

A wooden table with an egg and a tray of glasses sits indoors, offering a view through open French doors. A spacious patio area is visible beyond, framed by lush greenery and a distant tree. Light filters in, creating a bright and airy feel.

Cottage in Fife

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.

4.99 out of 5 average rating, 139 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.

4.99 out of 5 average rating, 320 reviews

The entrance of the annex apartment is framed by lush green foliage and a well-maintained garden. A vibrant red door is centered under a decorative gable, highlighted by the natural stone exterior of the building. A window above allows light to filter in.

Home in Cupar

Charming self contained annex apartment

Charming self contained annex apartment overlooking beautiful walled gardens. Located in a quiet area of the historic market town of Cupar and close to St Andrews and Edinburgh. This two floor self contained apartment has private gardens and ample off street parking. The upper floor provides an open plan kitchen, dining and snug area. The shower room and bedroom with king size bed is located on the ground floor. Cupar is a perfect location to explore Fife and surrounding areas.

5 out of 5 average rating, 212 reviews

Cottage in Freuchie

Charming, vintage style cottage with free parking

Holmlea is a cosy, sandstone cottage c. 1840, nestled in a quiet, pretty little road in the friendly village of Freuchie. With light, spacious, high-ceilinged rooms, Holmlea has an arty, vintage style, and is a welcoming, comfortable and relaxing space. There is free parking in the road opposite the cottage, and a large, free car park (25m away). Most of our guests tell us they feel instantly at home on arrival, and many don't want to leave! Licence No. FI 00095 F EPC rating D

4.98 out of 5 average rating, 130 reviews

A panoramic view of rolling green hills stretches across the landscape, dotted with trees and bushes. A wooden fence lines the property, enhancing the natural scenery. The sky showcases a blend of blue hues, with soft clouds transitioning from light to darker shades.

Home in Fife

Stunning holiday 'Retreat' with WOW factor!

In an elevated position with stunning panoramic views, the Retreat is a wonderful & unique getaway to relax and unwind - equally suitable as a romantic retreat for two as for an active family. Furnished to a high standard, with all your needs - outside play tennis, relax in the lovely garden, or enjoy the surrounding countryside, including 10 acres of private farmland. Centrally located - St Andrews (golf & beach) 20 mins. Train station to Edinburgh 10 mins drive.

4.91 out of 5 average rating, 104 reviews

The traditional stone cottage is surrounded by a well-maintained lawn and framed by lush greenery. The entrance features a pair of large black doors beneath a symmetrical window arrangement, while a satellite dish is mounted on the side.

Cottage in Cupar

Garden Cottage, nr St Andrews.Glorious location!

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.

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Other great vacation rentals in Cupar

5 out of 5 average rating, 6 reviews

A blue felt pool table is positioned on a wooden deck surrounded by greenery. The table displays a triangle of colorful billiard balls at one end, while a white cue ball is placed nearby. Soft outdoor lighting enhances the inviting atmosphere.

Holiday park in Fife

Laffs Lodge

5 out of 5 average rating, 91 reviews

A wooden sign featuring a friendly dog illustration, holding a sign that reads 'Please Wipe Your Paws.' The design includes cartoonish paw prints, contributing to a welcoming atmosphere for guests and their pets.

Cottage in Fife

Charming Country Cottage with Private Gardens

A cream-colored compost bin with a wooden handle is positioned next to a potted succulent. The bin's label is clearly marked with the word 'COMPOST.' Natural light filters through the window, illuminating the setup on a bright, clean surface.

4.74 out of 5 average rating, 84 reviews

Blue Moon Holiday Home in Cupar

Home in Fife

4.94 out of 5 average rating, 104 reviews

Balass Lodge near The Old Course St. Andrews

5 out of 5 average rating, 11 reviews

A narrow stone pathway is flanked by historic buildings, leading to a wrought iron railing arching over the walkway. A section of a white utility box is visible on the wall beside a window, while a light fixture hangs above, casting soft illumination.

Apartment in Fife

Southbridge Studio

4.97 out of 5 average rating, 78 reviews

An outdoor seating area, made of stone, surrounds a sandy circular fire pit. In the background, the cabin can be seen with multiple windows. The landscape is open, featuring wild grasses and a view of the sea under a clear sky.

Vacation home in Fife

Rustic Cabin 10, sea views & highland cows

A narrow alleyway is framed by a textured stone wall and a white cottage wall. The entrance door is sheltered by a distinctive awning, complementing the overall character of the quaint architecture. Soft natural light illuminates the surroundings, enhancing the inviting atmosphere of the space.

Apartment in Cupar

4.71 out of 5 average rating, 76 reviews

Charming freshly decorated cottage flat