Vacation rentals in Pitlessie

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Top-rated vacation rentals in Pitlessie

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Guest favorite

The unique exterior of the cabin is showcased, featuring a distinctive angled structure with a circular window. The dark metal cladding contrasts with the natural greenery surrounding the building. A wooden door is visible, leading to a welcoming entrance area.

Cabin in Craigrothie

4.89 out of 5 average rating, 146 reviews

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

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, 109 reviews

Luxury River View Farm Cottage + Dog Friendly

Enjoy stunning views over the River Tay from a luxury countryside base (35 mins from St Andrews & 50 mins from Edinburgh). Old Parkhill is a beautifully restored 3 bedroom farm cottage, featuring a stylish open plan space, designer kitchen, wood burning 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.

Guest favorite

A round stone structure features a grand portico with an ornate archway and decorative details. Lush green grass surrounds the building, complemented by a backdrop of trees displaying autumn foliage. The clear blue sky adds brightness to the tranquil setting.

Tower in Edinburgh

4.96 out of 5 average rating, 181 reviews

Craigiehall Temple (historic property built 1759)

Make you trip to Edinburgh truly memorable with a stay at Craigiehall Temple. Built in 1759 and situated in its own grounds on a former part of the Craigiehall Estate, it's Grade A listed for its stunning portico displaying the arms of the 1st Marquess of Annandale. A plaque on the wall carries a quote from Horace: "Dum Iicet in rebus jucundis vive beatus", "Live happy while you can among joyful things". We hope that a stay at the Temple will deliver this experience and stay true to this vision.

Top guest favorite

A charming entrance is framed by lush, green foliage and colorful flowers. The white door is partially visible, nestled among climbing plants. Sunlight casts gentle shadows on the pathway, creating a welcoming approach to the cottage.

Tiny home in Falkland

4.97 out of 5 average rating, 147 reviews

❤️ Cottage experience in the heart of Falkland! ❤️

A truly romantic experience! Couples who deserve a cottage break can't look past this! The Little Dundrennan Cottage is in the heart of the stunning Falkland. A beautiful garden full of beautiful flowers and colourful plants will delight you from March till October. The cottage was a stable in the 17th and 18th centuries and now is a pleasant and charming place to stay. Enjoy a king size bed, cozy conservatory, blackout curtains, kitchen amenities , SMART tv, Netflix, wifi and other facilities.

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

4.97 out of 5 average rating, 148 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.

Guest favorite

An open plan living area features a round wooden dining table surrounded by four black chairs. Two red and gray striped armchairs are positioned nearby, next to a wooden cabinet. Natural light enters through two large windows with beige curtains, while a stone wall adds character.

Cottage in Blebocraigs

4.99 out of 5 average rating, 109 reviews

Clatto Bothy, self catering cottage.

Clatto Bothy is a recently refurbished, fully furnished semi-detached cottage less than five miles from St Andrews. The self catering accommodation consists of a spacious open plan kitchen and dining area and a large living space. There is one double bedroom and a large shower room. The cottage sleeps two and offers peaceful surroundings within easy reach of St Andrews. The kitchen is fully equipped including washing machine and dishwasher. The Bothy has its own private parking area.

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, 331 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

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, 134 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.

Top guest favorite

The grand facade of Dollarbeg Castle is presented, showcasing its gothic baronial architecture. A circular gravel driveway leads to the entrance, framed by well-maintained green lawns and mature trees in the background, under a clear blue sky.

Castle in Dollar

4.98 out of 5 average rating, 185 reviews

The Great Hall, Dollarbeg Castle

This 2 bedroom apartment is the beautifully converted former Great Hall of Dollarbeg Castle. Built in 1890, Dollarbeg Castle was the last gothic baronial style building of its type ever built. Beautifully restored in 2007 to the very highest standards, it was converted into 10 luxury properties, one of which is a conversion of the original "Great Hall" with its vaulted ceiling and majestic views across the formal grounds towards the Ochil Hills in the distance.

Top 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

4.9 out of 5 average rating, 105 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, 103 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, 898 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.