House holiday rentals in Cupar

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Top-rated house rentals in Cupar

Guests agree: These houses are highly rated for location, cleanliness and more.

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Guest favourite
A spacious living area is shown, featuring large windows that provide expansive views of the surrounding landscape. Comfortable seating includes two leather armchairs and a sofa adorned with cushions. A light coffee table sits on a patterned rug, contributing to the inviting atmosphere.
Home in Glenfarg
4.97 out of 5 average rating, 190 reviews

Hillside Well Cottage

Hillside Well Cottage is a family run 4 bedroom cottage set in a beautiful, peaceful location in the Perthshire countryside, with spectacular views of the Lomond Hills bordering Fife. It is centrally situated, and a perfect base for visiting many places of interest including Edinburgh, Glasgow, Stirling, Pitlochry, Gleneagles, St Andrews, Perth and Dundee. Also, locally, the East Neuk, Falkland and Kinross on the banks of lovely Loch Leven offer many attractions and are well worth a visit.

Top Guest favourite
A spacious dining area is surrounded by large windows, offering views of the garden and natural surroundings. A wooden table is set for eight, complemented by comfortable brown chairs. A unique chandelier crafted from antlers hangs above the table, enhancing the inviting ambiance.
Home in Rumbling Bridge
4.89 out of 5 average rating, 212 reviews

Shiel House, Rumbling Bridge

Set in 3 acres of gardens and with beautiful views of the valley, Shiel House is the perfect retreat. This bespoke house was built by our family to provide an escape from the city and it has been furnished to provide a comfortable home from home. It would suit solo adventurers, couples, families (including with kids), and groups. Centrally located, and only an hour's drive from Edinburgh, Glasgow, Perth and St Andrews, it is the ideal base for golfers, walkers and visitors to Scotland.

Top Guest favourite
The lounge features a light-toned sofa and an armchair adorned with colorful cushions. A coffee table is positioned in the center, complemented by a plant. A modern television is mounted on the wall, with a corner fireplace adding a cozy touch. Natural light flows through a large window.
Home in Fife
4.98 out of 5 average rating, 199 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

Top Guest favourite
The charming farmhouse with a stone facade stands prominently in a peaceful setting, framed by a white picket fence. Flowers bloom at the entrance, complementing the spacious gravel driveway, which provides a welcoming approach to the inviting home.
Home in Fife
4.98 out of 5 average rating, 123 reviews

Beautiful 4 bdrm Farmhouse with ocean views, Fife.

Drinkbetween Farmhouse has recently been refurbished. Sleeping anywhere from 4 up to 8 guests it is ideally situated in a beautiful & peaceful rural setting on Banchory Farm, just 40 minutes from Edinburgh. There is a large contained garden. It has spectacular views over the fields to the ocean so you can truly relax. However, for those who love to explore, it’s ideally located close to some of Scotland’s most iconic towns like St Andrews, Elie or Gleneagles, all just 40 minutes away.

Superhost
A historic stone structure spans over the river, featuring two arches and a tower. Surrounded by lush greenery, the building displays intricate architectural details. Clear blue skies reflect off the water, enhancing the serene rural landscape.
Home in Ballintuim
4.89 out of 5 average rating, 697 reviews

Bridge Cottage, Magical 2 bedroom apartment

If your looking for something a little different then the stable wing of The Bridge House may be just for you! My unusual holiday home is part of the unique Bridge House built over the River Ardle in k1881. It has recently been renovated to a warm and cosy standard! Charming original features including stone spiral stairs, traditional Scottish timber clad walls, brick and pine flooring. All mod cons including wifi & smart TV. Quiet, peaceful and rural location. Pretty views.

Top Guest favourite
A cozy fireplace is framed by decorative tiles and a collection of logs nearby, inviting warmth. A woven basket holds additional firewood. The scene includes a glimpse of a piano in the background, alongside a rug and floral decor, enhancing the homely feel.
Home in Kinghorn
4.97 out of 5 average rating, 159 reviews

Muma Bears House

This is Muma Bears house and it always will be. She was my Mother and this is what me and my girls always called her. She passed in June 2021 and i have spent the last year renovating her house. She was a force and i hope we have done her proud. I want the house to come alive. So welcome! Cosy up in front of the fire, play the piano and unwind in peace. Bring along your slippers. Get the board games out and relax with family and friends. Enjoy the sound of the fire at night.

Guest favourite
Home in Leuchars
4.87 out of 5 average rating, 259 reviews

No 67 Modern 2‑Bed Nr St Andrews - Free Parking

Welcome to No 67, a bright, modern ground‑floor apartment ideally located in Leuchars, perfectly positioned between St Andrews and Dundee. The upstairs apartment, No 65, is also available on Airbnb. This comfortable two‑bedroom apartment is furnished to a high standard, with fresh, contemporary décor creating a light and airy feel throughout. Free Wi‑Fi, gas central heating, and a fully equipped kitchen make it equally suited to short breaks, longer stays, or work trips.

Top Guest favourite
A spacious bedroom features a large bed with soft linens and decorative pillows. Two bedside lamps provide warm lighting. A vintage dresser and an armchair are positioned nearby, while a mirror reflects the soft tones of the room. Light filters through the window adorned with patterned curtains.
Home in Alyth
4.93 out of 5 average rating, 150 reviews

Rural cottage retreat with hot tub

Jordanstone's Orchard Cottage is a perfect getaway for two couples or a small family. Comfortable, cozy and nestled in quiet part of a beautiful estate, the Orchard Cottage is well laid out across a single-storey. It is adjacent to an apple orchard which forms part of the walled Victorian estate, in which there is plenty of space to walk and be with nature. With a top of the line hot tub and a secure garden for your little furry friend, this cottage won't disappoint!

Top Guest favourite
The water tower, a distinctive architectural feature, is showcased against a twilight backdrop. Soft illumination from the windows highlights the structure's unique silhouette, while dark trees surround the base, enhancing its presence in the tranquil landscape.
Home in Dalkeith
4.98 out of 5 average rating, 124 reviews

The Historic Dalkeith Water Tower

The water tower is a bespoke home in an historic building sensitively converted by its architect owner. The tower is located in the historic town of Dalkeith and the settlement of Eskbank. 20 minutes by car from Edinburgh airport. A bus service into Edinburgh stops every 10- 15 minutes, the bus stop is a 2 minute walk away. 25 minutes by rail to the Scottish Borders or to the centre of Edinburgh from the local Eskbank Train Station, a 20 minute walk from the tower.

Top Guest favourite
A large conservatory is depicted, featuring abundant natural light streaming through the glass roof and numerous windows. A wooden dining table runs the length of the room, accompanied by several blue candle holders. Comfortable seating is arranged along one side, overlooking a lush garden.
Home in Fife
4.96 out of 5 average rating, 160 reviews

The Vintage - A Hidden Gem close to the Old Course

The Vintage... A well-struck 2-iron away from the 1st tee of the Old Course, 100 yards from the seafront and close to the town center. Tucked away but in the middle of it all, The Vintage is a delightful, free-standing, fully renovated, three bedroom house with a large conservatory and a unique private patio garden. Located in the conservation area, with no direct access for cars, the only noise one hears is the wind and the occasional seagull flying overhead.

Top Guest favourite
A stone cottage is set among a landscaped garden, featuring a gravel pathway. The structure displays a traditional design with multiple windows and a slate roof. Colorful flowers bloom in front, contributing to the rural charm of the setting.
Home in Wester Balgedie
4.99 out of 5 average rating, 186 reviews

Ashtrees Cottage

Ashtrees Cottage is in a beautiful rural location and has Loch Leven Nature Reserve on its door step. The Balgedie Toll Tavern & Loch Levens Larder both less than 10 minutes walk from the Cottage. It’s a great place to explore towns and villages around the East Neuk of Fife, Edinburgh, St Andrews, Gleneagles, Stirling and Glasgow. Its a great place to base yourself if you are planning to explore the Lowlands and Southern Highlands of Scotland.

Top Guest favourite
A well-maintained garden area features a gravel surface bordered by artificial grass. Outdoor seating is provided with a table and chairs set. Decorative features include two statues and circular wooden planter beds, creating a relaxing outdoor environment.
Home in St Andrews
4.97 out of 5 average rating, 170 reviews

Number 3 St Andrews

Comfortable 2 bedroom home, well equipped for self catering. Non smoking. Front access 4 steps, rear 1 step. Lovely, sheltered sunny garden with outside seating/table at rear. Local hosts. Nearby facilities include convenience shops/M&S Food hall/Aldi and Morrisons Supermarket/10 min walk St Andrews town centre also local bus service to town/15-20 min walk to Golf area and West Sands/15min walk to East Sands and indoor leisure centre.

Popular amenities for Cupar house rentals

Quick stats about house rentals in Cupar

  • Total holiday rentals

    Explore 10 holiday rentals in Cupar

  • Nightly prices starting at

    Cupar holiday rentals start at $84 AUD per night before taxes and fees

  • Verified guest reviews

    Over 550 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    10 of Cupar holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cupar rentals

  • 4.9 Average rating

    Cupar stays are highly rated by guests—averaging 4.9 out of 5!

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