Vacation rentals in Pitlessie

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Top-rated vacation rentals in Pitlessie

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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, 228 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

An open plan kitchen and dining area features a rustic wooden table surrounded by black chairs, positioned beside a large window with a view. Navy cabinetry complements the stainless steel appliances, while white walls and elegant light fixtures enhance the space's brightness.

Cottage in Newburgh

5 out of 5 average rating, 114 reviews

Luxury River View Farm Cottage + Dog Friendly

Enjoy stunning views over the River Tay from a luxury countryside base (35 mins to St Andrews & 50 mins to Edinburgh). Old Parkhill at Hyrneside is a beautifully restored 3 bed farm cottage, featuring a stylish open plan space, designer kitchen, wood stove and heated polished concrete floors. Relax in marble washrooms, one with a clawfoot bath, the other a walk-in shower. French doors open out to a courtyard dining area + pizza oven, fire pit and acres of farmland, forest + trails to explore.

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, 149 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, 389 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 facade of a charming stone house is framed by vibrant greenery and a gravel pathway. Large windows on either side of the entrance provide ample light. A striking red door serves as the focal point, complemented by an assortment of potted plants scattered around the front yard.

Home in Cupar

4.99 out of 5 average rating, 339 reviews

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.

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, 222 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

4.94 out of 5 average rating, 141 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.

Top 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

4.98 out of 5 average rating, 143 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, 108 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.

Top guest favorite

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, 166 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.

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, 105 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.

Top guest favorite

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, 917 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.