Vacation rentals in Cupar

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Top-rated vacation rentals in Cupar

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Guest favorite

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 8 – 15

G$26,568 GYD per night

Guest favorite

Tiny home 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

G$27,023 GYD per night

Guest favorite

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 16 – 23

G$38,908 GYD per night

Guest favorite

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.

Oct 9 – 16

G$28,999 GYD per night

Guest favorite

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.

Aug 23 – 30

G$71,302 GYD per night

Guest favorite

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

Mar 4 – 11

G$21,426 GYD per night

Guest favorite

Home in Fife

4.99 out of 5 average rating, 101 reviews

Coastal 2 bedroom house - golf/ beach getaway

Lovely bright and cheerful House with access to private garden, in a lovely fife coastal village. The House has good walking access to local attractions including being only 2 minutes from Scotscraig Golf Club (13th Oldest in the World) and 10mins from the stunning Kinshaldy Beach with views over the river Tay, The village also has several charming cafes, bars and local shops. Tayport is nestled between Dundee and the Historic Town of St Andrews. Short-term let licence - F1 00160F

Jan 21 – 28

G$21,796 GYD per night

Guest favorite

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 15 – 22

G$22,921 GYD per night

Guest favorite

Cottage in Fife

4.98 out of 5 average rating, 193 reviews

Braeview: Cosy studio farm cottage near St Andrews

We have lovingly converted a 200 year old cartshed 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.

Nov 29 – Dec 6

G$30,815 GYD per night

Guest favorite

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

Mar 8 – 15

G$21,472 GYD per night

Guest favorite

Home in Fife

4.94 out of 5 average rating, 239 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 23 – 30

G$28,518 GYD per night

Guest favorite

Loft in New Gilston

4.95 out of 5 average rating, 439 reviews

The Wynd, near Peat Inn, St Andrews

The Wynd is situated in the middle of New Gilston country hamlet, stop at the red phone box and you have found us. We are 10 minutes from StAndrews and 2 minutes from the Peat Inn Restaurant. Overall, a good quality place to stay, close enough to enjoy everything the area has to offer yet secluded and private to relax. COVID advice : Be reassured that our place is completely independent and clean. Letting Licence : FI 00301 F

Nov 20 – 27

G$27,811 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cupar vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Cupar's top sights

Lidl7 locals recommend

ALDI Cupar5 locals recommend

The Boudingait9 locals recommend

Isle of May National Nature Reserve4 locals recommend

Co-op Food - Cupar3 locals recommend

The Courtyard6 locals recommend

Other great vacation rentals in Cupar

Guest favorite

Guest suite in Fife

4.98 out of 5 average rating, 114 reviews

Idyllic B&B in the Fife Lomond Hills

Oct 5 – 12

G$24,112 GYD per night

Guest favorite

Vacation home in Auchterhouse

4.98 out of 5 average rating, 123 reviews

Rowanbank Cabin - a gorgeous country escape

Nov 27 – Dec 4

G$35,156 GYD per night

Guest favorite

Cottage in Lower Largo

4.96 out of 5 average rating, 745 reviews

Weaver’s Cottage beach getaway

Feb 5 – 12

G$35,640 GYD per night

Guest favorite

Hut in Perth

4.96 out of 5 average rating, 636 reviews

Tranquil and Cosy Perthshire Cabin

Nov 9 – 16

G$20,005 GYD per night

Guest favorite

Cabin in Kincaple

5.0 out of 5 average rating, 135 reviews

Bright and Cosy Luxury Countryside Cottage

Jan 1 – 8

G$31,894 GYD per night

Guest favorite

Guest suite in Fife

4.99 out of 5 average rating, 106 reviews

Pluck the Crow Annex (FI 00062 F)

Apr 8 – 15

G$29,098 GYD per night

Guest favorite

Cabin in Inverkeilor

4.98 out of 5 average rating, 196 reviews

Cabin & Hot Tub on smallholding with Alpaca's +

Nov 24 – Dec 1

G$31,243 GYD per night

Guest favorite

Place to stay in Newburgh

4.96 out of 5 average rating, 115 reviews

‘ Burgher Chapel- Converted Church’

Feb 25 – Mar 4

G$18,529 GYD per night

Show all

Quick stats about vacation rentals in Cupar

Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
G$4,171 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Cupar have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Cupar. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cupar have wifi?
Absolutely! We offer over 20 house rentals with wifi in Cupar. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Cupar?
Four-legged friends are welcome in Cupar. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Cupar have free parking?
Absolutely! We offer over 10 house rentals with free parking in Cupar. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Cupar?
Cupar has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Cupar?
Yes! Work meets play with ease at over 10 vacation rentals in Cupar featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Cupar?
Experience the best of Cupar with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in Cupar?
Make yourself at home in Cupar by choosing from our most frequently booked neighborhoods. We have over 60 vacation rentals in Cupar Muir, and over 140 vacation rentals in Cupar.

Vacation rentals in Cupar

Top-rated vacation rentals in Cupar

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Cupar vacation rentals

Stay near Cupar's top sights

Other great vacation rentals in Cupar

Guest suite in Fife

Vacation home in Auchterhouse

Cottage in Lower Largo

Hut in Perth

Cabin in Kincaple

Guest suite in Fife

Cabin in Inverkeilor

Place to stay in Newburgh

Quick stats about vacation rentals in Cupar

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Cupar have a kitchen?

Do house rentals in Cupar have wifi?

Are there pet-friendly vacation rentals in Cupar?

Do house rentals in Cupar have free parking?

Are there family-friendly vacation rentals in Cupar?

Are there vacation rentals with a dedicated workspace in Cupar?

How much does it cost to stay in house rentals in Cupar?

Where should I stay in Cupar?

Destinations to explore