Photo by Eddie Boyd

Cupar Holiday Rentals

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Holiday Rentals in Cupar

Fridge, microwave, oven, stovetop
Carters Cottage is a 200 year old fully refurbished stone built weavers cottage.
10.0 out of 10, Exceptional, (143)
"Excellent property, central location to visit all the major attractions of Fife and beyond, very comfortable with an excellent hostess. Really enjoyable stay."
Carters Cottage is a 200 year old fully refurbished stone built weavers cottage.
Exterior
Holmlea Cottage, a sweet and charming getaway in a picturesque Fife village.
10.0 out of 10, Exceptional, (11)
"Great situation, in a very friendly little village. Close to some great short walks, both Lomond Hills are within easy reach. Close to St Andrews, and the East Nook of Fife. Would love to return."
Holmlea Cottage, a sweet and charming getaway in a picturesque Fife village.
Club Apartment | Living area
No.1 St Andrews and Westpark House Bedrooms
4.0 star property
9.6 out of 10, Exceptional, (141)
"This property was very comfortable convenient and in a beautiful place. The portraits on the hallway walls were creepy."
The price is NZ$443
includes taxes & fees
2 Jun - 3 Jun
No.1 St Andrews and Westpark House Bedrooms
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Exterior
Traprain Cabin ( Lammermuir views )
10.0 out of 10, Exceptional, (9)
"Absolutely beautiful stay. The lodge itself was gorgeous, in a great setting and the views are spectacular. Quiet and peaceful, no disturbance whatsoever. The surroundings are just spectacular. We mentioned it was our little minimoon and they very kindly left us some chocolates and a bottle of fizz. Amazing stay exactly what we needed. Wish we could have stayed longer xxxx"
Traprain Cabin ( Lammermuir views )
Interior
1st floor flat/free parking/WiFi 2 bedroom/2 bathroom sleep 5 The Shore Tramstop
9.6 out of 10, Exceptional, (239)
"Quick walk to the tram to access downtown and close to the waterfront. Host provides lots of information on the area and local attractions. "
The price is NZ$539
includes taxes & fees
27 May - 28 May
1st floor flat/free parking/WiFi 2 bedroom/2 bathroom sleep 5 The Shore Tramstop
Smart TV, fireplace, DVD player, books
Cosy cottage near Elie, beaches, golf, great base for East Neuk
9.0 out of 10, Wonderful, (65)
"We stayed in Colinsburgh for a month and loved it. The cottage had all we needed, the town had all we needed. Maia is always responsive and ready to guide and help with any questions."
Cosy cottage near Elie, beaches, golf, great base for East Neuk
Beach nearby
Romantic Boutique Bolthole In Pittenweem Near St Andrews. Small dogs welcome.
9.8 out of 10, Exceptional, (71)
"Lovely cottage, modern fittings and original features blended well. Well equipped and a convenient location. Shame the galleries in the village weren’t open as it was out of season and limited eating out options. Local people friendly and helpful. Would go again"
Romantic Boutique Bolthole In Pittenweem Near St Andrews. Small dogs welcome.
Beach
This is the property to stay if you like a seaview
10.0 out of 10, Exceptional, (48)
"We loved it so much that we have booked again for a week in October."
This is the property to stay if you like a seaview
TV
Delightful 2 bedroom apartment in Leith
6.0 out of 10, (6)
"Very good location, nice and clean and good sleeping arrangements."
The price is NZ$466
includes taxes & fees
4 Jun - 5 Jun
Delightful 2 bedroom apartment in Leith
3 bedrooms, iron/ironing board, travel cot, free WiFi
Luxury flat 2 mins from tram stop in the 4th coolest neighbourhood in the world!
9.4 out of 10, Exceptional, (23)
"We enjoyed our stay in the apartment. The location was nice just out of the hustle and bustle of the big city."
Luxury flat 2 mins from tram stop in the 4th coolest neighbourhood in the world!
House | Interior
The Neuk Anstruther, Sleeps 6 Fantastic Location
3.5 star property
10.0 out of 10, Exceptional, (6)
"We had a lovely stay i the cosy and recently refurbished The Neuk. Thoroughly enjoyed it and found it to be plenty space for a family of 6!"
The Neuk Anstruther, Sleeps 6 Fantastic Location
Property grounds
APARTMENT WITH STUNNING SEA VIEWS IN PITTENWEEM NEAR ST ANDREWS
10.0 out of 10, Exceptional, (269)
"This was our third stay in this wonderful apartment which is ideal for exploring the East Neuk. Everything you need is in the flat and if there are any issues the owner is happy to help. We will be back (as long as it's not already fully booked)!"
APARTMENT WITH STUNNING SEA VIEWS IN PITTENWEEM NEAR ST ANDREWS
Exterior
The Arns Cottage is a traditional stone built, cosy and luxurious retreat.
10.0 out of 10, Exceptional, (4)
"Arns cottage was a perfect respite from the rigour of hotel stays. Our host made us feel so welcome. Katie has thought of everything for travellers to enjoy their surroundings Loved the heated floors, the charm & decor of Arns cottage. We’ll be back Patrice and Ian"
The Arns Cottage is a traditional stone built, cosy and luxurious retreat.
Private kitchen
PARKING & LIFT ACCESS - A beautiful, modern central apartment.
10.0 out of 10, Exceptional, (122)
"The condo was nice and clean. Had plenty of room and everything you’d need for your stay. Much better than a hotel."
PARKING & LIFT ACCESS - A beautiful, modern central apartment.
Fridge, microwave, oven, stovetop
The Neuk, 2 Bedroom Apartment in Stunning Coastal Town Location.
10.0 out of 10, Exceptional, (62)
"A notebook was provided with every detail about the property imaginable, along with appliance manuals. Property was spacious and comfortable! Just remember to hold the handle up on the exterior door while engaging the deadbolt! Wonderful location to Cellardyke and a quick walk to Anstruther. Would’ve liked to had more time to walk the Coastal Path."
The Neuk, 2 Bedroom Apartment in Stunning Coastal Town Location.
Exterior
Idyllic location; sleeps 2; accessible; wood burner; dog friendly (pet fee)
10.0 out of 10, Exceptional, (91)
"We recently enjoyed a delightful weekend getaway at Chapelton Cottage. The cottage itself is charming and impeccably clean. It has everything we needed for a relaxing stay, including a cozy fireplace, a comfortable bed, a fully-equipped kitchen and many other extras. We were fortunate with the weather and spent most of the evening time outside enjoying a BBQ and the massive firepit. The location was perfect for anyone seeking a getaway from the hustle and bustle and we would highly recommend...
Idyllic location; sleeps 2; accessible; wood burner; dog friendly (pet fee)
Beach nearby
Coastal 1 bedroom cottage with sea views- The Shore
9.0 out of 10, Wonderful, (13)
"The Shore is a very cosy and comfortable one bedroom cottage/flat. It is very well-equipped, nicely furnished and spotlessly clean. It was very easy to communicate with the host and nothing was too much trouble. The area is very beautiful with plenty to do, including beach walks, exploring the villages of the East Neuk of Fie, and enjoying the lovely cafes, pubs and restaurants . The cottage is an ideal base for discovering this charming part of Fife. We thoroughly enjoyed our short break at...
Coastal 1 bedroom cottage with sea views- The Shore
7 bedrooms, iron/ironing board, WiFi, bed sheets
Hot tub, beautifully restored Manse. Fantastic midweek rates available.
10.0 out of 10, Exceptional, (96)
"Great stay for a group of 13 from Grandparents through to Grandkids. Pet friendly an added bonus. Great location with lots to do."
Hot tub, beautifully restored Manse. Fantastic midweek rates available.
Providing Stylish City Living within the vibrant shore area
9.0 out of 10, Wonderful, (6)
"Great local transport links into Edinburgh and cheap too. Fish market restaurant nearby-very good."
Providing Stylish City Living within the vibrant shore area
Deluxe Apartment | Living area
No1. Apartments St Andrews - South Street
4.0 star property
9.8 out of 10, Exceptional, (18)
"Only things not perfectly for room4 was too noisy the bus stop and drunk people shouting on the street . "
The price is NZ$803
includes taxes & fees
27 May - 28 May
No1. Apartments St Andrews - South Street
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See all available properties in Cupar
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Cupar you may be interested in

Exterior
Apex City Quay Hotel & Spa
4.0 star property
9.2 out of 10, Wonderful, (1005)
"Lovely hotel and great facilities. "
The price is NZ$156
includes taxes & fees
27 May - 28 May
Apex City Quay Hotel & Spa
Breakfast, lunch, dinner served; British cuisine
Dakota Edinburgh
3.5 star property
9.2 out of 10, Wonderful, (1002)
"Easily accessible to airport and motorways"
The price is NZ$271
includes taxes & fees
2 Jun - 3 Jun
Dakota Edinburgh
Indoor pool, pool loungers
Village Hotel Edinburgh
4.0 star property
8.2 out of 10, Very good, (1001)
"Enjoyed our stay very much all staff overall were helpful very friendly and happy 😊"
The price is NZ$385
includes taxes & fees
24 Jun - 25 Jun
Village Hotel Edinburgh
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cupar holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cupar. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cupar. Seeing all the best attractions is bound to make you fall in love with Cupar. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cupar short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Cupar?

Yes, there are holiday rentals in Cupar close to Cairnie Fruit Farm & Mega Maze, or you can select a more secluded option if you're looking for a relaxing stay. Cupar is known for its golf courses and bars.

What are some of the best holiday rentals that Cupar has to offer?

Family house near Elie, golf, beaches, sea views, half term discount!: This holiday home rental outside Cupar is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Cupar?

Expedia has 30 holiday rentals for your stay in Cupar.

What’s there to see and do in Cupar?

Family-friendly attractions include Cairnie Fruit Farm & Mega Maze and The Scottish Deer Centre, whereas Falkland Palace and Fife Coastal Path are a couple of great spots to enjoy the outdoors. While here, Raptor World Interactive and Backhouse Rossie Estate are other places worth a visit.

What’s a holiday rental in Cupar like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cupar. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for small groups.

Recent reviews of Cupar properties
Expedia verified reviews