Vacation rentals in Pitlessie

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Top-rated vacation rentals in Pitlessie

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Top guest favorite
A charming stone cottage is set against a clear blue sky, surrounded by lush green lawns and trees. The building features large windows and a red roof, providing a welcoming appearance. The well-maintained grounds offer ample outdoor space for relaxation.
Cottage in Peat Inn
4.99 out of 5 average rating, 207 reviews

Eastburn: Gorgeous 2-bed cottage near St Andrews

Eastburn Cottage was created from our lovingly converted 200 year old cartshed. On 13 acres of grounds accessed via a 400 metre track, Braeside Farm is tranquil yet a 10-15 minute drive to St Andrews and less than an hour from Edinburgh Airport. Eastburn is a 2 bedroom cottage (the one on the right) with a kitchen and living room upstairs and a master bedroom (en suite) and smaller bedroom (with a triple bunk bed), bathroom and WC downstairs. Front door is at the top of the steps in the gable.

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, 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 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, 168 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.

Top guest favorite
The vibrant yellow exterior of a historic country house is complemented by lush greenery and mature trees in the foreground. A sunlit lawn surrounds the building, enhancing the inviting atmosphere of the property.
Apartment in Falkland
4.96 out of 5 average rating, 157 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 favorite
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, 234 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' - 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

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, 150 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
A single-story stone cottage is set against a cloudy sky, featuring a metal roof and black window frames. A neatly landscaped garden with colorful flowers is positioned in front, while a wooden fence and pathway lead to the entrance.
Cottage in Lundin Links
4.94 out of 5 average rating, 397 reviews

Beautiful stables conversion in rural location

The stables is a recently developed single story cottage on Hatton Farm. This quiet rural location is 1km from Lundin Links. Finished & furnished to a high standard the property is well equipped with everything you will need to enjoy your stay. Fully contained garden with a private patio & bbq area to the rear, ideally positioned to enjoy the morning & evening sun. Only a few minutes to the local beach, pub, shops & golf courses. St Andrews & the East Neuk villages are close by.

Top guest favorite
The front exterior of the sandstone cottage features a welcoming blue door, complemented by white-framed windows. Flanking the entrance are potted plants and neatly trimmed shrubs, creating an inviting appearance. The slate roof adds character to this charming abode.
Cottage in Freuchie
5 out of 5 average rating, 224 reviews

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

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
4.93 out of 5 average rating, 146 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 fantastic food all day; the Hayloft and Pillars of Hercules are lovely cafes. Fine dining at the Boar's Head in nearby Auchtermuchty.

Guest favorite
Panoramic views of rolling green hills and farmland are displayed, with distant mountains visible under a partly cloudy sky. Lush fields stretch across the landscape, dotted with trees and farm buildings, creating a serene natural environment.
Home in Fife
4.97 out of 5 average rating, 146 reviews

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.

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 exterior of a historic manor house is framed by manicured lawns and vibrant greenery. Soft hues of sunset create a serene backdrop. The two-story structure displays multiple windows and a traditional architectural style, contributing to its timeless appeal.
Home in Springfield
4.99 out of 5 average rating, 107 reviews

Edenfield House, Springfield, Fife

Edenfield is a stunning private Manor house, dating back to the 17th century. Nestled in private grounds on the outskirts of the market town of Cupar and just a short drive from St Andrews, the home of golf with royal connections, it is ideally located to explore the beautiful north east coastline and the perfect spot for golfers. With enough space for 12 guests, it’s also the perfect place for get togethers and celebrations with friends and family.

Popular amenities for Pitlessie vacation rentals

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