Find and Book Top Rated Holiday rentals in Cupar

Search among 11 available holiday rentals in Cupar from 50+ providers

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Great11 reviews
4 adults
2 bedrooms
2 beds
MapView on map300 m from City Centre100 m from The Ceramic Experience
From   US$ 157 /nightSelect
Perfect9 reviews
7 adults
2 bedrooms
5 beds
MapView on map100 m from City Centre200 m from The Ceramic Experience
From   US$ 149 /nightSelect
14.4 km from City Centre500 m from Laing Museums
From   US$ 138 /nightSelect
From   US$ 131 /nightSelect
Great1 review
From   US$ 76 /nightSelect
From   US$ 152 /nightSelect
14.8 km from City Centre100 m from Laing Museums
From   US$ 122 /nightSelect
The Wee Hideaway
14.8 km from City Centre100 m from Laing Museums
From   US$ 90 /nightSelect
Wonderland Cottage
14.8 km from City Centre100 m from Laing Museums
From   US$ 125 /nightSelect
East Cottage - Tarvit
2.8 km from City Centre
From   US$ 201 /nightSelect
Rhum Cottage
9.1 km from City Centre
From   US$ 820 /nightSelect

Best Vacation Rentals in Cupar

Why visit?

With its charming historic buildings and picturesque countryside, Cupar is a delightful destination for tourists. Located in the heart of Fife, Scotland, this town offers a peaceful and authentic Scottish experience. Cupar boasts several notable landmarks, such as the historic Cupar Old Parish Church and the grand Cupar Castle, both of which provide a glimpse into the town's rich history. Additionally, the nearby Scottish Deer Centre offers a unique opportunity to observe native Scottish wildlife up close. Whether you're interested in history, nature, or simply escaping the hustle and bustle of city life, Cupar has something to offer for every tourist.

Why is choosing vacation rentals in Cupar better than staying in a hotel?

More space and privacy: Vacation rentals in Cupar provide the luxury of having an entire property to yourself, allowing for more space and privacy compared to a hotel room.

Local experience: By staying in a vacation rental, you can immerse yourself in the local community and experience the town like a resident.

Fully equipped kitchens: Most vacation rentals in Cupar come with fully equipped kitchens, giving you the option to cook your own meals and save money on dining out.

Flexibility: With vacation rentals, you have the freedom to come and go as you please, without adhering to strict hotel schedules or check-in/check-out times.

Value for money: Vacation rentals often offer great value for money, particularly for families or large groups, as you can split the cost among several individuals.

Vacation rentals in Cupar


The Old Surgery Flat: A cozy and well-equipped apartment located in the heart of Cupar, within walking distance of local shops and restaurants.

Cupar Cathedral Apartment: This modern apartment offers a perfect blend of comfort and convenience, with stunning views of the nearby St. John's Church.

The Jute Store: Set in an idyllic countryside location, this stylish apartment features rustic decor and easy access to scenic walking trails.


The Old Mill House: A charming stone cottage with a spacious garden, located just outside Cupar. This traditional Scottish house offers a peaceful retreat.

Cupar Cottage: This recently renovated cottage combines modern comfort with traditional Scottish charm. The property features a private garden and is close to local amenities.


The Thatchers: A beautifully restored townhouse in the heart of Cupar, offering elegant accommodation with period features and a cozy fireplace.

The Malt House: This townhouse boasts contemporary interiors and a central location, making it the ideal base for exploring Cupar and its surroundings.

Luxury rentals:

The Whisky Barrel Lodge: An exquisite log cabin with luxurious amenities, including a hot tub and sauna. Located in a secluded area, this unique rental offers a truly indulgent experience.

Cupar Castle Retreat: Situated within the stunning grounds of Cupar Castle, this elegant retreat features period furnishings and access to manicured gardens.

Homes with a pool:

The Country House: This spacious and beautifully designed home offers a private swimming pool and large outdoor area, perfect for family gatherings.

The Manor House: With its grand rooms and stunning views, this historic property boasts a private pool and is ideal for those seeking a luxurious getaway.

Waterfront/Near beachfront:

The Harbour View: This waterfront apartment offers magnificent views of the harbor and is just a short drive away from the beautiful beaches of Fife.

Cupar Bay House: Located within walking distance of the beach, this charming holiday home provides a tranquil setting near the coast.

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