Vacation rentals in Cupar

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Quick stats about vacation rentals in Cupar

  • Total vacation rentals

    Explore 30 vacation rentals in Cupar

  • Nightly prices starting at

    Cupar vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,650 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Cupar vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cupar rentals

  • 4.8 Average rating

    Cupar stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Cupar

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A view of the outdoor space captures a lush green lawn, dotted with blooming daffodils. A small birdbath stands in the foreground, while a tree shows autumn hues. An expansive countryside scene unfolds in the background, framed by a wooden fence.
Cottage in Fife
5.0 out of 5 average rating, 61 reviews

Fife Farm Cottage Nr St Andrews

A spacious detached 3 bedroom cottage, situated on our working arable farm. All bedrooms have super king beds which can be split into singles with bed linen & towels provided. With wonderful views over the countryside there is plenty of outdoor space to explore or sit and enjoy from the patio. A large lounge, with an open fire for the winter. Local amenities close at hand, with family friendly activities. Plenty of local restaurants or enjoy dining in. Only 6 miles from golfing at St Andrews.

Superhost
Condo in Fife
4.75 out of 5 average rating, 101 reviews

Stylish Fife Flat by Home of Golf, St Andrews

The Blue Moon Holiday Home is our spacious flat located right in the heart of Cupar. Close to St Andrews Old Course, Peat inn Michelin star-restaurant and the Hill of Tarvit-walk. The flat is decorated by an interior designer who has given full attention to creating a lovely getaway for couples, friends or families in a stylish holiday home- using sustainable materials, furniture & paints. The West Sands beach of St. Andrews and the St. Andrews Aquarium is only a short drive away. Pets welcome!

Guest favorite
A charming two-story stone building features a dark front door with side windows. Flower boxes adorn the windowsills, while neatly trimmed bushes line the stone boundary. The facade displays a warm, inviting character, set along a quiet street.
Condo in Cupar
4.99 out of 5 average rating, 145 reviews

Luxury central ground floor flat (nr St Andrews)

Lovely 2 bedroom ground floor flat in the centre of Cupar, Fife. Private entrance. Outdoor enclosed seating area/courtyard (sun trap when weather is good). Quirky, cosy & comfortable. High quality kitchen & shower room. 20 min. drive to St Andrews, Dundee & East Neuk. Train station/buses less than 10 min. walk. Very central - one way quiet street. Supermarkets, Butcher, Baker, Post office, Chemist, Cafes, Take-away, Deli, Bars, Bistros and car parking all within a few minutes walk.

Top guest favorite
A wooden gate with a sign labeled 'Treehouse' opens to a path leading through lush greenery. Tall trees surround the entrance, with the Treehouse visible in the background, nestled among the branches and foliage.
Treehouse in Letham
4.95 out of 5 average rating, 121 reviews

Real Fairytale Treehouse

Set within the grounds of Fernie Castle a beautiful authentic Treehouse with 6 living Trees growing and thriving. Equally beautiful in all seasons especially winter being so very cozy, it is fully heated with lots of hot water for the freestanding bath for two. With all the amenities of a 5 star bedroom, a large freestanding bath on the second floor with a small balcony with views to the stunning countryside it does indeed feel like a fairytale just remember to bring your favourite bubbles...

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
4.94 out of 5 average rating, 271 reviews

Craigiehall Temple (historic property built 1759)

Make your 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, its 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 wooden railing frames a scenic view of the Tay estuary, showcasing calm waters reflected under a cloudy sky. In the distance, a bridge spans the river, integrating nature and structure in a tranquil setting.
Condo in Fife
4.99 out of 5 average rating, 260 reviews

The Waterfront

Overlooking the Tay estuary this stunning flat has views to take your breath away. A patio, a deck, and a quirky waterfront garden create an idyllic paradise. A luxe new shower room and stylish bedrooms create a unique holiday spot. Enjoy dinner on the deck or walk to excellent neighbouring restaurants. This newly launched flat from the 1860s is recently refurbished. It is close to Dundee and St Andrews and on the fife coastal path. A golfers paradise. An hour to the Cairngorms or Edinburgh.

Guest favorite
An open-plan kitchen and living area features a circular kitchen island with seating. A ladder leads to a loft space, and natural light enters through a skylight and window. Warm wood flooring complements the decor, while a red accent curtain adds a touch of color.
Cottage in Fife
4.95 out of 5 average rating, 170 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.

Top guest favorite
A secluded retreat is nestled among vibrant yellow fields, with lush green hills and a rocky peak in the background. The white structure is surrounded by trees, showcasing an inviting rural landscape under a partly cloudy sky.
Guest suite in Brunton
4.99 out of 5 average rating, 80 reviews

Brunton Hill

Come and be rejuvenated in our beautiful, peaceful space - relaxing (luxuriously) in nature, with expansive views, leaving all your cares behind. Brunton Hill can offer you a quiet and very comfortable space to retreat, exploring the very local scenery, walking the dog or on bikes; or, as a base from which to visit St Andrews (16 miles) , Fife Coast and beaches, Dundee and the V&A (12 miles), Southern Cairngorms and Perthshire. For a bird’s eye view look up Brunton Hill Retreat on YouTube.

Top guest favorite
An open plan living area features high exposed wood beams and a cozy seating arrangement with a blue sofa and armchair. A wooden coffee table sits centrally, and light filters through double doors leading to the outside. A dining space and kitchen area are visible in the background.
Barn in Fife
5.0 out of 5 average rating, 99 reviews

The Roundel in Fife

Reconnect with nature at this unforgettable escape. ‘The Roundel’ near Cupar is a beautiful restored barn with its own private entrance. It offers a unique and private sanctuary for guests exploring the beautiful surrounding areas. This lovely open plan space forms part of what was once a traditional farm steading and sits in a quiet and peaceful setting. Guests also have use of a tennis court within the grounds. St Andrews, with its famous golf courses and beaches is just 20 mins by car.

Top guest favorite
A gravel pathway leads through a landscaped area featuring colorful flowering plants and lush greenery along a stone wall. The buildings are visible in the background, showcasing a modern design with a gabled roof and large windows reflecting the outdoor scenery.
Condo in Fife
4.99 out of 5 average rating, 176 reviews

The Bothy; Cosy Country Hideaway near St Andrews

Welcome to The Bothy ! A recently renovated barn space forming a stunning 1 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 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.

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
4.98 out of 5 average rating, 123 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.

Guest favorite
A view from a window overlooks a vibrant street scene in Cupar, featuring a mix of traditional and modern buildings. The foreground reveals a corner store with a distinct sign, while the sky is dotted with clouds and sunlight, creating a lively atmosphere.
Townhouse in Fife
4.93 out of 5 average rating, 88 reviews

Number •6•

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.

Popular amenities for Cupar vacation rentals

When is the best time to visit Cupar?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,123 GYDG$26,985 GYDG$26,985 GYDG$24,893 GYDG$29,495 GYDG$29,914 GYDG$32,215 GYDG$34,097 GYDG$26,985 GYDG$27,613 GYDG$25,730 GYDG$26,357 GYD
Avg. temp4°C4°C6°C8°C10°C13°C15°C15°C13°C10°C6°C4°C

Frequently Asked Questions

  • What are the best places to stay in Cupar?

    Many visitors choose accommodations around the town centre for easy access to shops, dining, and historic sites. The countryside around Cupar also has characterful cottages for those seeking a quieter experience.

  • What are the best things to do in Cupar with kids?

    Families often enjoy Cupar’s play parks, hands-on exhibits at local museums, and animal encounters at nearby farms. Walking trails and outdoor gardens provide open spaces for exploration and picnics.

  • What are some of the best things to do in Cupar?

    Explore Cupar Heritage Centre, wander the landscaped grounds of Hill of Tarvit Mansion, and browse independent shops in the town centre. Nearby woodlands and parks create inviting spaces for outdoor activities.

  • How is the weather in Cupar?

    Cupar has cool winters around 33–44°F (1–7°C) and mild summers reaching up to 67°F (19°C). Rainfall is common year-round, so packing waterproof layers is often suggested.

  • When is the best time to visit Cupar?

    Late spring through early autumn is often recommended for milder temperatures, blooming gardens, and outdoor events. The changing leaves create a colorful scene in local parks during autumn.

  • What are the best places to visit in Cupar?

    Cupar Heritage Centre, Hill of Tarvit Mansion, and local markets are often highlighted. Historic churches and the riverside create distinct backdrops for strolls and photography.

  • What are some hiking trails in Cupar?

    Explore woodland paths around Tarvit Hill, gentle riverside trails along the Eden, or maintained walks in public parks. Country estates near Cupar often have marked routes for different abilities.

  • What are some family activities we can do in Cupar?

    Visit play parks, share hands-on learning at museums, or enjoy meet-and-greets with animals at local farms. Open-air picnics, craft workshops, and family-friendly walking trails are also popular.

  • What are some of the best day trip ideas from Cupar?

    Venture to nearby coastal villages for historic harbors, walk ancient castle grounds, or sample foods at rural farm shops. Scenic viewpoints and traditional craft workshops make for engaging outings around the region.

  • Are there any pet friendly accommodations available in Cupar?

    Cupar has a selection of pet-friendly accommodations, including vacation rentals and self-catering cottages. You can find places near local green spaces for walks with your pet.

  • What are some local tips for visiting Cupar?

    Explore Cupar’s markets for fresh produce, try local cafes for a taste of regional baking, and check event calendars for seasonal fairs. Embrace changeable weather by planning both indoor and outdoor activities.

  • What is Cupar known for?

    Cupar is known for its market town heritage, historic architecture, and a strong agricultural tradition. The area has well-preserved gardens, nearby castles, and vibrant local food culture.

  • What are the best hidden gems to explore in Cupar?

    Discover peaceful walks along the River Eden, tucked-away bakeries serving traditional treats, or historic churches with unique stained glass. Small galleries and local craft shops showcase creative work from the region.

  • What are the best foods to try in Cupar?

    Cupar’s dining scene includes traditional Scottish pies, locally produced cheeses, and bakery treats like shortbread and scones. Seasonal produce from the area’s farms frequently appears in market stalls and dishes.

  • What should I bring for a trip to Cupar?

    Bring layers for changing weather, a waterproof jacket, comfortable shoes for walking, and an adapter for United Kingdom outlets. Outdoor clothing is useful if you plan nature walks or castle visits.

  • What is the nightlife in Cupar like?

    Cupar’s nightlife centers on cozy pubs, occasional live music sessions, and relaxed social clubs. Some venues in town feature locally brewed ales or traditional Scottish folk evenings.

  • What are the most popular events or festivals in Cupar?

    Cupar has frequently suggested events such as agricultural fairs, seasonal markets, and festivals that celebrate local music or produce. Country shows around summer and traditional pipe band gatherings draw visitors and locals alike.

  • Are there family friendly vacation rentals in Cupar?

    Family-friendly vacation rentals are available in Cupar, with options including cottages, townhouses, and rural homes. Many properties have amenities such as kitchens, gardens, and easy access to outdoor areas.