25 Best Vacation Rentals in Cupar - Holiday Lettings - Cabins

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28 Vacation rentals

(20) Excellent 

19

Fife Vacation home rental

Fife / Cupar

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
On the ground floor is a Living Room, Dining Room, Kitchen, Conservatory with slate bed pool table, Twin Bedroom and Family Bathroom.On the first floor there is another twin bedroom, a double bedroom and a shower room with W.C.The house backs onto open country s  …see more

from $95 / night

$599 - $725 / week

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from $95 / night

(4) Excellent 

21

Fife Vacation lodge rental

Fife / Cupar

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 20 mi
  • Child friendly
  • Pet friendly
Silver Birch, one of our 4 'Tree' Lodges, is located in a peaceful rural setting with excellent views over the surrounding Fife countryside. It is a well equipped lodge with a private hot tub on the decking and benefits from being pet friendly. The nearest towns are o  …see more

from $101 / night

$681 - $1053 / week

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from $101 / night

(2) Excellent 

16

Vacation cottage in Fife

Fife / Cupar

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 23 mi
  • Child friendly
  • Pet friendly
Idyllic 1 bedroom Cottage ideal for a quiet, romantic break away. Spacious bedroom with beautiful super king four-poster bed, stunning luxury bathroom with free-standing bath and separate power shower, open-plan fully equipped kitchen / dining / living room area with  …see more

from $114 / night

$769 - $1191 / week

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from $114 / night

18

Fife Vacation lodge rental

Fife / Cupar

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
Kingfisher is one of our 'Bird' lodges. All of these lodges have 2 bedrooms, 2 bathrooms and open plan kitchen / living / dining rooms. All Lodges at Balmeadowside have private decking with their own private hot tubs. The master bedroom is en suite and features a su  …see more

from $108 / night

$744 - $1122 / week

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from $108 / night

(4) Very Good 

23

Vacation lodge in Fife

Fife / Cupar

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
300 year old Georgian garden pavilion, modernised inside to offer everything you need for a weekend away from it all. The east pavilion offers a double room, a twin room and a single, all ensuite along with a well equipped kitchen and living room. The property is Set in  …see more

from $202 / night

$870 - $1386 / week

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from $202 / night

(19) Very Good 

20

Fife Vacation home accommodation

Fife / Cupar

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 14 mi
  • Child friendly
This self catering one bedroom cottage is situated in the picturesque village of Ceres, in North East Fife. Situated only 2 miles from Cupar and 7 miles from St Andrews, the historic centre of golf, boasting the oldest course in the world. It is also only 40 miles from  …see more

from $63 / night

$429 - $964 / week

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from $63 / night

10

Fife Vacation apartment rental

Fife / Cupar

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
  • Private garden
Moatville Upper is the first floor apartment of a detached Victorian villa in Cupar. It is possible to book both Upper & Lower together to make a sizeable property for a family or business group. Located on a quiet residential street just 2 minutes walk from the Co o  …see more

from $189 / night

$882 - $1103 / week

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from $189 / night

10

Vacation lodge in Fife

Fife / Cupar

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
This property is brought to you by TravelNest. Ref: 95782 Set in the Fife glens with stunning views of the surrounding countryside, the luxurious Bird Lodges are the perfect place to escape and relax in your own private hot tub! Sleeping up to  …see more

from $145 / night

$818 / week

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from $145 / night

17

Fife Vacation home rental

Fife / Cupar

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
This property is brought to you by TravelNest. Ref: 95734 Set in the Fife glens with stunning views of the surrounding countryside, the luxuriously modern Cherry Blossom Cottage is the perfect place to escape and relax in your own private hot tub!  …see more

from $158 / night

$846 - $1089 / week

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from $158 / night

(4) Very Good 

38

Vacation cottage in Fife

Fife / Cupar

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 14 mi
  • Child friendly
  • Private garden
Welcome to Garden Cottage. Garden Cottage is right in the heart of our country estate in Fife, about 9 miles from St Andrews and its many golf courses. The cottage has 2 bedrooms, and sleeps 4 plus baby or small child.. The cottage is detached, two storey, and sits in i  …see more

from $133 / night

$624 - $983 / week

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from $133 / night

11

Vacation lodge in Fife

Fife / Cupar

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
This property is brought to you by TravelNest. Ref: 95770 Set in the Fife countryside with stunning views of the surrounding area, the luxurious Tree Lodges are the perfect place to escape and relax in your own private hot tub! Sleeping up to  …see more

from $171 / night

$749 - $812 / week

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from $171 / night

(1) Very Good 

53

Vacation castle with golf nearby in Fife

Fife / Cupar

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
<p></p><br><p></p><br><p>Exceptional medieval castle lovingly restored to its original splendour sleeping up to 12 adults and 2 children over four floors. Set within a beautiful rural area with plenty of outdoor open space for c  …see more

from $343 / night

$2394 - $4410 / week

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from $343 / night

(11) Excellent 

25

Vacation cottage in Fife

Fife / Cupar

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 18 mi
  • Child friendly
  • Ask about pets
The Rings is a fully accessible holiday cottage that can take groups of varying sizes. Flexibility has been built in from the start and you can book as many or as few rooms as you wish as areas can be blocked off and used by other groups. Each room has it's own independ  …see more

from $13 / night

$89 / week

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from $13 / night

(4) Excellent 

13

Vacation apartment in Fife

Fife / Cupar

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden
If you looking for stay of more than 3 nights ask for weekly rate- it's cheaper than multiple nights. Spacious ground floor apartment with two large bedrooms, lounge, dining room, well equipped galley kitchen and shower room. Can be booked with the 3 bedroom Upper Moat  …see more

from $152 / night

$882 / week

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from $152 / night

16

Bungalow rental in Fife with golf nearby

Fife / Cupar

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Ask about pets
'WeeBothy' is a lovely one-bedroom apartment in a converted sandstone building, within steading style surrounds. Set in lovely Fife countryside, it is ideal for a short break in FIfe, with Cupar 5 miles away and St Andrews and the coast only 16 miles a  …see more

from $125 / night

$755 / week

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from $125 / night

(3) Excellent 

7

Cottage rental in Fife with golf nearby

Fife / Cupar

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 10 mi
  • Child friendly
  • Car not necessary
Cosy cottage in the conservation area of Cupar. Bright and sunny cottage within a few minutes walk of the town centre on quiet residential street. Living room with home office area, WiFi, 2 bedrooms, bathroom with over bath shower, kitchen with folding dining table.  …see more

from $126 / night

$441 / week

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from $126 / night

(13) Excellent 

9

Vacation home in Fife

Fife / Cupar

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Denmuir Arches is a luxury, contemporary conversion of a 19th century farm steading, set within the grounds of a working family farm in the Kingdom of Fife.The renovation has been completed to the highest standards, with four double bedrooms, three ensuite bathr  …see more

from $252 / night

$1008 / week

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from $252 / night

7

Vacation home in Fife

Fife / Cupar

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Set in the Fife glens with stunning views of the surrounding countryside, the luxurious Bird Lodges are the perfect place to escape and relax in your own private hot tub! Sleeping up to 4, all lodges come with 1 master bedroom with super kingsize bed and ensuite shower  …see more

from $118 / night

$818 / week

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from $118 / night

15

Vacation home rental

Fife / Cupar

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Pet friendly
Sleeps 8 2 super king size bedrooms (1 downstairs) 2 twin bedrooms Each room has en-suite shower, however master bathroom is shower over bath Open plan kitchen/dining/living area Fully fitted kitchen with range cooker and dishwasher Freeview TV and DVD player Wood burni  …see more

from $218 / night

$1525 / week

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from $218 / night

7

Vacation home in Fife

Fife / Cupar

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Set in the Fife glens with stunning views of the surrounding countryside, the luxurious Bird Lodges are the perfect place to escape and relax in your own private hot tub! Sleeping up to 4, all lodges come with 1 master bedroom with super kingsize bed and ensuite shower  …see more

from $118 / night

$818 - $819 / week

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from $118 / night

(1) Very Good 

14

Fife Vacation yurt accommodation

Fife / Cupar

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
The hobbit yurt is a charming one off yurt surrounded by woodland which offered ad regret of seclusion and privacy. There is a fully equipped kitchen and shower room your your use in an adjacent building. The hobbit yurt has a double bed and a futon which folds into a s  …see more

from $95 / night

$504 / week

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from $95 / night

41

Fife Vacation home rental

Fife / Cupar

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
Sleeps up to 4 1 king size master bedroom 1 twin bedroom 1 family bathroom with shower over bath Freeview TV, DVD player and iPod docking station Open plan kitchen/dining/living area Fully fitted kitchen with dishwasher Under floor heating Bed linen and towels provided  …see more

from $108 / night

$749 / week

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from $108 / night

(1) Very Good 

21

Vacation cottage in Fife

Fife / Cupar

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 17 mi
  • Child friendly
  • Ask about pets
A lovely spacious cottage set in rural Fife. South tower cottage is set in the grounds of Cairnie fruit farm, not far from Cupar and St Andrews. The property was converted recently from a coach house and stable into a large open plan kitchen, living room with 13ft barre  …see more

from $202 / night

$870 - $933 / week

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from $202 / night

42

Vacation home in Fife

Fife / Cupar

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Pet friendly
Sleeps up to 4 1 king size master bedroom 1 twin bedroom 1 family bathroom with shower over bath Freeview TV, DVD player and iPod docking station Open plan kitchen/dining/living area Fully fitted kitchen with dishwasher Under floor heating Bed linen and towels provided  …see more

from $171 / night

$749 / week

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from $171 / night

7

Vacation lodge in Fife

Fife / Cupar

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Services: Sleeps up to 4 1 super king size master bedroom with en-suite shower room 1 twin bedroom with en-suite shower room Freeview TV, DVD player and iPod docking station Open plan kitchen/dining/living area Fully fitted kitchen with dishwasher Private decking with h  …see more

from $145 / night

$818 / week

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from $145 / night

12

Vacation lodge in Fife

Fife / Cupar

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
This property is brought to you by TravelNest. Ref: 95764 Set in the Fife countryside with stunning views of the surrounding area, the luxurious Tree Lodges are the perfect place to escape and relax in your own private hot tub! Sleeping up to 4, all lodges come with 1  …see more

from $171 / night

$749 / week

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from $171 / night

13

Vacation b&b in Ladybank

Cupar / Ladybank

3 4 1 night min

  • 3 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Private garden
We opened our Bed & Breakfast service on Friday September 2nd 2016 and we are already so excited to welcome our guests! Downfield House and garden are centrally located in the Kingdom of Fife. It is a peaceful house surrounded by a beautiful garden where you can enjoy  …see more

from $38 / night

$265 / week

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from $38 / night

36

Vacation home in Fife

Fife / Cupar

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
Sleeps 4+child+baby. 2 bedroom beautiful, traditional stone built cottage set in our country estate nr Cupar in Fife. Free wi-fi. The tennis court is about 100 yards from the cottage and guests are welcome to use it by arrangement. The cottage has its own garden and ov  …see more

from $133 / night

$731 - $1071 / week

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from $133 / night