Vacation rentals in Cupar

4.91 out of 5 average rating, 128 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

4.91 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!

Now, 2 night stays available, June only. 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.

4.99 out of 5 average rating, 123 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.

Guest suite in Longforgan

A dark blue door is set against a wooden panel exterior, framed by horizontal lines. A sleek outdoor light fixture is mounted to the left of the door, while a stone slab serves as the doorstep, complemented by a gravel path.

4.97 out of 5 average rating, 332 reviews

Guest Suite with Private Entrance, close to Dundee

The Studio at Broadleaf is a cosy self contained Guest Suite in Longforgan, just outside Dundee. The Studio has a private entrance and parking with entrance hall and stairs up to the suite. The suite itself has a small kitchen, living and dining area with large TV, DVD and Netflix. There is a bathroom with Shower. Longforgan is near Dundee, one of the most up and coming cities in Scotland. We are only 30 minutes from St Andrews, 1 hour from Edinburgh, Glasgow and the Highlands of Scotland.

4.98 out of 5 average rating, 181 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, 140 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, 158 reviews

The cottage is set against a clear blue sky, with its stone exterior partially covered in a blanket of fresh snow. Sunlight reflects softly off the white surface, while the charming architectural features, including a large arched entrance, are highlighted by the winter setting.

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, 140 reviews

A charming outdoor seating area is framed by a lattice structure, featuring two wooden chairs with soft, fur seat covers. A small wooden table is set for two, surrounded by greenery and a view of the garden beyond.

Apartment in Falkland

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.

4.96 out of 5 average rating, 218 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, 238 reviews

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 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.

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.

4.99 out of 5 average rating, 138 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, 315 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.

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Popular amenities for Cupar vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Cupar

A central grill is situated within a wooden cabin, featuring a curved black hood above. Flames flicker from glowing coals beneath a hexagonal grill. Wooden benches surround a circular table, providing a cozy gathering space for enjoying meals.

Cabin in Fife

4.88 out of 5 average rating, 42 reviews

Rural Cosy Cabin With Beautiful Views Over Fife

DominicRating, 5 stars3 days ago

Largo Law by Wigwam was an absolutely lovely stay. The view is absolutely spectacular and really was the highlight of the stay. They had all the amenities they listed which made for a comfortable weekend stay. It is in a great location to get out to the beautiful coast and do some lovely walks. Would definitely come back

Home in Fife

4.69 out of 5 average rating, 78 reviews

Oasis Retreat Hot Tub Escape

ErikaRating, 5 stars3 weeks ago

We really enjoyed our stay — the town is lovely and full of charm. The place itself had everything we needed, was spacious enough, and felt clean and uncluttered. The jacuzzi was a great bonus and made the stay extra relaxing. Would definitely recommend!

A white ceramic container labeled 'Tea' is placed on a countertop, accompanied by two delicate cups featuring blue floral patterns. Behind them, a framed black and white photograph of a street scene adds an artistic touch to the arrangement.

4.75 out of 5 average rating, 83 reviews

Blue Moon Holiday Home in Cupar

FrancesRating, 5 stars2 months ago

Great place! Fabulous apartment So big I nearly needed google maps to get round it! Would definitely recommend this place to stay! It is full of character and colour ! Thank you .

4.9 out of 5 average rating, 30 reviews

The exterior of a stone building is featured, showcasing large sash and case windows that reflect natural light. Surrounding trees with autumn foliage create a serene atmosphere on the pathway leading to the entrance.

Apartment in Freuchie

The Old Linen Mill

GinnyRating, 5 stars1 month ago

Shirley was a marvellous host - sharing info in good time prior to arrival & going out of her way to accommodate us arriving a little early. The flat itself was beyond expectations with a great layout & homely touches. Beautifully decorated & extremely comfortable with plenty of space. Light & clean with great windows overlooking the horse paddock & the views beyond. The beds were clean & comfy, a great shower in the bathroom & fab range in the kitchen where we enjoyed making meals each day. Our car sat nav originally led us the wrong way once we got to the village but Shirley’s description was spot on once we followed that. Freuchie is a small peaceful place & ideally located to go on day trips up the coast towards Crail & St Andrews or further up North past Perth up to Dunkeld. We enjoyed Falkland hill & going to the Pillars of Hercules organic farm shop & cafe nearby & would happily stay here again as it was a real home from home with fantastic features to make you feel relaxed.

Home in Fife

4.94 out of 5 average rating, 103 reviews

Balass Lodge near The Old Course St. Andrews

RobRating, 5 stars2 weeks ago

Dougal was always responsive whenever we had a question. He was extremely flexible in whatever we asked of him. One tiny tidbit is that the coffee maker is tiny, especially in a house of that size. I would suggest he buy a normal size coffee maker. But overall the kitchen was well equipped, the property was clean and comfortable and just a 20-minute drive into St. Andrews. Would definitely recommend it.

5 out of 5 average rating, 16 reviews

The exterior of the 18th Century doocot displays a charming stone facade complemented by wooden accents. Large windows allow ample natural light, while a well-maintained gravel courtyard features colorful flower pots near the entrance. Lush greenery surrounds the property, enhancing the serene setting.

Home in Pittenweem

Stylish and peaceful getaway for two

HannahRating, 5 stars1 week ago

Great stay at the Doocot. Really well done out accommodation, which was the perfect place to explore Fife and surrounding areas. We particularly enjoyed walking part of coastal path, Cambo gardens, Loch Lomond and the Cairngorms. Lisa was fantastic at communicating, and gave us so many great recommendations. Only slight negative was the lack of space for hanging/storing clothes. It was our first time in Fife and we absolutely loved it!

Superhost

Apartment in Fife

4.9 out of 5 average rating, 42 reviews

Unique Apartment sleeping 7 close to St Andrews

HannahRating, 5 stars11 months ago

What a fun, historic and beautiful place! The renovations make it welcoming and stylish. We enjoyed our stay here and never felt like we needed anything, as all our basic needs were provided for. This is definitely a unique stay that is a must book if you’re in the area!