Vacation rentals in Pitlessie

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Top-rated vacation rentals in Pitlessie

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Guest favourite
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
4.94 out of 5 average rating, 161 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.

Top guest favourite
A charming stone cottage with a yellow front door is surrounded by greenery and gravel pathways. Features include two prominent front windows that allow natural light to fill the interior and a sloping roof that complements the rustic aesthetic.
Cottage in East Wemyss
4.97 out of 5 average rating, 201 reviews

No 2 Stable Yard, Wemyss Castle Estate

A home from home in the Fife countryside and only a few minutes' walk from the seashore. No 2 Stable Yard is an attractive, bright and comfortable cottage in a newly renovated stable conversion; a peaceful rural retreat at the historic Wemyss Castle Estate. Perfectly placed for exploring Scotland it suits families, couples & groups of friends looking for a cosy getaway. 30 miles from Edinburgh, a short drive to the East Neuk and St Andrews with numerous golf courses and lots more in between.

Top guest favourite
Apartment in Falkland
4.96 out of 5 average rating, 160 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, 303 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, 266 reviews

Braeview: Cosy studio farm cottage near St Andrews

We have lovingly converted a 200 year old cart shed 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
The exterior of 'The Howff' is showcased, featuring a quaint structure with a grey stone finish and a chimney. Surrounding lush greenery and rolling hills provide a natural backdrop. A small garden area with flowering plants is visible, enhancing the rural ambiance.
Tiny homes in Balbeggie
4.99 out of 5 average rating, 185 reviews

Writer's Retreat in the heart of Perthshire

'The Howff' is a refurbished farm worker's bothy in a rural location with lots of walks and access to beautiful parts of Perthshire. One hour's drive from Edinburgh, 20 mins Dundee or Perth. This authentic bothy contains one room with single bed, wood burning stove, mini kitchen unit with fridge, oven, portable hob and kettle, separate shower room, wc, basin. Linen and towels included. Although small, The Howff is warm and cosy and makes a perfect retreat. Please note for ONE only.

Top guest favourite
An open living space features a round dining table with four chairs and a cozy sitting area. A woodburning stove stands beside a television, providing warmth. Natural light enters through a skylight and large window, enhancing the soft color palette of the walls and decor.
Condo in Fife
4.99 out of 5 average rating, 167 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
The exterior of the tiny house features traditional stone walls and a sloping roof. A blue door serves as the entrance, framed by two white windows. The cobblestone path leads to a small, manicured grassy area, with warm light reflecting off the building during sunset.
Tiny homes in Kinnesswood
4.99 out of 5 average rating, 104 reviews

Tiny House in Cosy Village

Dating back to the 1700s, this tiny house had sat empty for over 50 years until George (Heather's son) invested his life savings to completely renovate it to a high standard, while retaining the original character of the building. Sitting below Bishop Hill in the picturesque village of Kinnesswood (2023 joint winner of Britain in Bloom's 'Village' category!), the tiny house is surrounded by breathtaking views, fantastic walks, and an abundance of local farm shops, cafes, and restaurants.

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, 109 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
A two-story guest suite is set in a spacious yard, surrounded by greenery and trees. Large windows provide light to the stone-gray exterior. The well-maintained lawn features small shrubs and rocks, creating a serene environment, ideal for relaxation and outdoor enjoyment.
Guest suite in Glenrothes
4.98 out of 5 average rating, 172 reviews

Idyllic 2-bedroom suite in the Fife Lomond Hills

*** STAY 2 NIGHTS OR LONGER AND PAY 20% LESS PER NIGHT*** Explore Fife from the comfort of this cosy 2-bedroom guest suite in the beautiful Formonthills woodland on the edge of the Lomond Hills. Quiet and secluded yet close to tourist hotspots and three of Scotland's largest cities, Formonthills Steading is a haven for walkers, cyclists, holidaymakers or guests seeking a base from which to explore surrounding areas. Your booking gives you sole access to the whole guest suite.

Top guest favourite
An aerial view captures the charming coastal village, displaying a mix of colorful homes lining the shoreline. Rocky terrain transitions to grassy hills in the background, with the sea gently lapping against the shore, creating a serene seaside atmosphere.
Home in West Wemyss
4.99 out of 5 average rating, 181 reviews

Stylish Courtyard House in Fife Coastal Village

The Wall House was converted in 2020 from an historic fishing net repair building - it's old outside but super energy efficient & modern inside. It’s a truly unique, stylish and comfortable place to be. The Wall House is also designed to be accessible to a person with restricted mobility. Set in a Fife seaside conservation village you’ll find yourself in a 'get away from it all' location but just a short drive to Edinburgh, the East Neuk & St Andrews.

Top guest favourite
The exterior of Weaver’s Cottage features a stone construction with a tiled roof, surrounded by a lush green lawn. Colorful shrubs and plants enhance the garden area, while neighboring buildings display a mix of yellow and white facades. Outdoor seating arrangements invite relaxation.
Cottage in Lower Largo
4.97 out of 5 average rating, 969 reviews

Weaver’s Cottage beach getaway

Weaver’s Cottage, built from stone probably in the 18th century (the main house dates from 1687) sits in a large south facing garden with direct access to the designated bathing beach and the Fife coastal path. Lovingly restored it’s a wonderful place to relax, swim, go for beach walks, gaze at the stars in front of a cosy fire pit.

Popular amenities for Pitlessie vacation rentals

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