Vacation rentals in Cupar

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Top-rated vacation rentals in Cupar

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Guest favourite

Guesthouse in St Andrews

4.94 out of 5 average rating, 182 reviews

Self-contained cottage, 2 miles from St Andrews.

Self contained wee cottage with en-suite. Living room has feature stone wall, fully equipped kitchen and patio doors opening onto the garden. Best suited for a couple with 1 double bed in the bedroom. Chair-bed suitable for child or small adult for £20 extra. Travel cot available on request. Well-behaved pets welcome but NOT to be left on their own, garden is enclosed but not secure. Complimentary breakfast for the first morning, plus tea, coffee and condiments. Slow wifi STRICTLY NO SMOKING

Sep. 3 – 10

$172 CAD per night

Guest favourite

Tiny homes in Falkland

4.98 out of 5 average rating, 116 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.

Sep. 4 – 11

$183 CAD per night

Guest favourite

Cottage in Fife

4.99 out of 5 average rating, 163 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.

Dec. 8 – 15

$209 CAD per night

Guest favourite

Cottage in Fife

4.96 out of 5 average rating, 135 reviews

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.

Nov. 14 – 21

$262 CAD per night

Guest favourite

Barn in Fife

4.9 out of 5 average rating, 154 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.

Dec. 4 – 11

$197 CAD per night

Guest favourite

Barn in Dairsie

4.99 out of 5 average rating, 113 reviews

The Bothy; new barn conversion near St Andrews

Welcome to The Bothy ! A newly renovated barn space forming a stunning one 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 brand 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.

Mar. 17 – 24

$264 CAD per night

Guest favourite

Cottage in Freuchie

4.99 out of 5 average rating, 182 reviews

Charming, vintage style cottage with free parking

Holmlea is a cosy, sandstone cottage c. 1840, nestled in a quiet, pretty and historic tiny 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

Feb. 2 – 9

$147 CAD per night

Guest favourite

Townhouse in Fife

4.94 out of 5 average rating, 35 reviews

Newly renovated 3-bedroom townhouse in Cupar, Fife

The 3 bedroom property (sleeps 6 guests) is located in Cupar town centre, with all essential facilities, transport links and amenities within a short walking distance. This traditional building is full of character, and offers a bright and spacious stay for guests. A private access door is located to the rear of the building, abundant free car parking is available. Cupar is located in North East Fife, only 9 miles from St Andrews, 13 miles from Dundee and 47 miles from Edinburgh.

Jan. 18 – 25

$229 CAD per night

Guest favourite

Home in Cupar

4.98 out of 5 average rating, 260 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.

Oct. 10 – 17

$149 CAD per night

Guest favourite

Cottage in Ceres

4.95 out of 5 average rating, 181 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 and secure garden, great for dogs. Its 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, butcher, pub and coffee shops. St Andrews and Cupar are nearby. Provisional Licence Number: FI 00488 P

Dec. 7 – 14

$142 CAD per night

Guest favourite

Home in Fife

4.94 out of 5 average rating, 238 reviews

The Cupar House. Bright and spacious home/garden.

Fife council registration number (STL): FI 00760 P Historic detached House with a lovely, secluded, mature garden. 4 bedrooms (1 en-suite). Patio doors onto garden with garden seating. Off street private parking for 1 vehicle. On street free for additional vehicles. Easy access to St.Andrews, Cupar, Perth, Edinburgh, Dundee, etc. Cupar train station is 10 minutes walk away. We have BT unlimited fibre broadband, BT TV and also freeview. No pets please.

Sep. 11 – 18

$275 CAD per night

Guest favourite

Cottage in Lower Largo

4.96 out of 5 average rating, 742 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.

Jan. 25 – Feb. 1

$235 CAD per night