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Holiday Homes in Oakham

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    Travellers to Oakham are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    All 37 Rentals in Oakham
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    Rutland view1 / 18
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Garden Apartment, Manton Lodge1 / 22
    (17)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The Walled Garden, Rutland1 / 18
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and unwind at this lovely holiday property by the wood-burning stove, or venture further afield and enjoy the Rutland countryside. . Step to entrance. Ground Floor: Living room: With wood burner, 50' Sky Q TV (family & full sports packages), DVD player with a selection of DVDs, CD player with...
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    LE15 8RZ, Wing, Oakham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Home from Home in oakham, Rutland1 / 17
    (9)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Certificate of Excellence
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2019
    Oakham is a good base to visit Rutland Water and the surrounding areas, it offers plenty of choice for places to eat out and some lovely shops, as well as its own heritage The...
    Reviewed 8 November 2018
    We had a really lovely time in Oakham. The house was perfect, really comfortable, clean and well equipped. Tracey had thought of everything from milk in the fridge to toiletries...
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    About this property
    Beautifully presented, comfortable three bedroomed, 1 king size, 1 double and 1 bunkbedded home from home with Wi-Fi, within walking distance to Oakham town centre, where you will find plenty of Pubs and delicious eating places. Fully fitted kitchen with washing machine, cooker, fridgefreezer and...
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    LE15 6QP, Oakham, Rutland
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    The Chapel - Wing. RUTLAND.1 / 36
    (35)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Housekeeping Included
    • Patio
    • Balcony
    • Wi-Fi
    • Central Heating
    • Washer
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2019
    My friend and I loved our stay at The Chapel. The architect designed interior has wow factor, is very comfortable, has plenty of storage space and is very well equipped. Colin...
    Reviewed 18 January 2019
    Lovely clean accommodation with everything we needed. Colin was great bringing us extra logs for the log burner, as it did get a bit cold downstairs. We had a great time and...
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    About this property
    ABOUT THE CHAPEL: The Chapel, Wing is an early 19th Century stone built Grade II listed Methodist Chapel sympathetically converted at the turn of the 21st Century to create a unique Modernist open plan house. Winner of The George Phillips Award and featured in 'Living Etc.' magazine. Set in the...
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    LE15 8RZ, Wing, Oakham
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    The Gallery Apartment, Oakham, Rutland1 / 15
    (18)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • DVD Player
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    • Balcony
    • Central Heating
    • Private Garden
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2019
    I stayed here with my daughter and mother for a couple of nights. The flat is in a great location, quiet and central. Very clean and functional. Hope to book again...
    Reviewed 1 July 2019
    Oakham is a surprisingly interesting market town and Wendy’s Apartment provided the perfect location with excellent facilities. I only needed the car to venture further afield...
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    About this property
    A two bedroom self catering apartment situated in the centre of the historic market town of Oakham. The building was converted to an apartment in 2015 and provides accommodation on the first floor with two bedrooms accommodating four guests, a sitting room with dining and kitchen area, a...
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    LE15 6AE, Oakham, Rutland
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Valley View Apartment, Manton Lodge Farm1 / 24
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2019
    Spent an amazing 5 weeks at this beautiful apartment prior to moving into our new home. Caroline met us on arrival and showed us round, explained everything about the apartment...
    Reviewed 17 September 2018
    The apartment is part of Lodge Farm with beautiful views across the fields and down on to Caroline's fabulous gardens. Large double bed and comfortably furnished. The kitchen is...
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    About this property
    Manton Lodge Farm is a beautifully-positioned 18th-century stone farmhouse set in more than 100-acres of privately owned rolling grassland in rural Rutland. It nestles in a fold in the landscape and boasts far-reaching views across the Chater valley. The property lies on the edge of Manton village...
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    LE15 8SS, Manton, Oakham
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Jubilee House - town centre property in Oakham1 / 21
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 28 July 2019
    Fantastic location in the town, parking space right behind the property. It was exceptionally clean and tidy, all the amenities you need. Nicholas was very helpful and responded...
    Reviewed 28 July 2018
    We were delighted with the house, it was beautifully clean with crisp bed linen and fluffy white towels. A short walk from the town centre with its own parking space and a small...
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    About this property
    Jubilee House is in a quiet side street just off the main High Street in Oakham. It sleeps six in comfort with 4 bedrooms, so ideal for families. It has all mod cons you would expect in a house including fully equipped kitchen and 3 bathrooms. Walking distance to numerous restaurants and pubs and...
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    LE15 6NG, Oakham, Rutland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Sticky End - Thatched Rutland Luxury Holiday Cottage1 / 22
    (25)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Garden
    • Parking
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2019
    A warm welcome, a cosy English cottage with every thing you could need plus more. Wonderful hosts and friendly village. Location is a huge plus too with so much to do in the...
    Reviewed 26 August 2019
    We have been staying at Sticky End since 2014 every August to attend Birdfair. It always feels like a home from home, except our own house does not have nearly so many...
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    About this property
    STICKY END: Ideal for couples and perfect for a romantic escape, this charming Grade II Listed thatched cottage has been lovingly restored and furnished to a very high standard to provide a warm and welcoming holiday or short break retreat. Sticky End is located in the busy & bustling conservation...
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    LE15 7DL, Oakham, Rutland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This modern retreat sits near Oakham in Rutland and can sleep six people in three bedrooms.Clipsham is located close to Oakham in Rutland. It provides three bedrooms which include two doubles, one of which has an en-suite, a twin/double and a family bathroom, the property is able to sleep six...
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    log cabin with hot tub free fishing Primrose1 / 12
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    • Hot Tub
    • Central Heating
    • Balcony
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    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 February 2019
    Lovely long weekend break for a valentines gift to the partner we both had the best weekend and he enjoyed the fishing. We fished 2 lakes over the weekend and had a lovely few...
    Reviewed 1 May 2017
    Great location to see Rutland from. We didn't go for the fishing but it looked good! The cabin was spotless, spacious and well equipped. The hot tub was brilliant and wonderful...
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    About this property
    Stretton lakes is situated within 120 acres of farmland in the picturesque county of Rutland. 4 luxury round log cabins are surrounded by woodland and set overlooking our fishing lakes. Our award winning 4 & 5* lodges are finished to an exceptionally high standard. Each lodge has its own private...
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    LE15 7QS, Oakham, Rutland
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This up-to-date lodge rests near the town of Oakham in Rutland, it is able to sleep four people in two bedrooms.Egleton which comes near Oakham in Rutland. The two bedrooms here are made up of a double with an en-suite and a twin/double room, it also offers a bathroom, the property is able to sleep...
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    A superb retreat nestled close to the town of Oakham in Rutland, sleeping up to four people in two bedrooms.Barrowden is a sleeps four retreat situated near to Oakham in Rutland, East Midlands. It comes with two bedrooms, made up of a double with an en-suite and a twin/double room with en-suite....
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lodge is located in the village of Whitwell, near Worksop, and can sleep six people in three bedrooms.Ashwell is a lovely lodge situated near the village of Whitwell, Rutland. Hosting three bedrooms; a double with en-suite, a twin, and a bunk room, along with a bathroom, this property can...
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    A detached timber lodge with Lake Views, available XMAS week 23rd Dec -30th Dec1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Balcony
    • Central Heating
    • Washer
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2020
    Cosy, really good facilities, everything was spot on. People at réception were helpful. Definitely recommand it !
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    About this property
    A detached timber-framed lodge with Lake Views of Rutland Water & full usage of Leisure complex. Ground floor – double en suite, one twin, family bathroom, separate WC. First floor – open plan lounge/diner/kitchen. TV, DVD player, twin bedroom. Outside balcony with table & chairs overlooking the...
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    LE15 8AB, Barnsdale, Oakham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    GLASTON, stylish interior, open-plan, Exton1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This fashionable wooden retreat sits near the town of Oakham and is able to sleep four people in two bedrooms.Glaston is tastefully furnished Retreat is situated close to the Rutland town of Oakham. It benefits from two bedrooms which include a double with an en-suite as well as a twin/double, it...
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This single-storey retreat is based near the town of Oakham and can sleep six people in three bedrooms.Seaton is close to the Rutland town of Oakham. Containing three bedrooms that are made up of two doubles, one of which boasts an en-suite, as well as a twin/double, along with a family bathroom,...
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    A superb modern retreat placed close to the Rutland town of Oakham, it sleeps four people in two bedrooms.Brooke is a fashionable wooden retreat three miles from Oakham in Rutland. It hosts two bedrooms which include a double with an en-suite as well as a twin/double, there is also a bathroom, the...
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This detached retreat sits near the Rutland town of Oakham, it is able to sleep four people in two bedrooms.Cottesmore is a tasteful retreat situated three miles from Oakham in Rutland. Its two bedrooms include a double with an en-suite along with a twin/double room, again with en-suite bathroom....
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    A ground floor retreat placed close to Oakham in Rutland, it can sleep up to four people in two bedrooms.Tickencote is a cedar-clad retreat located three miles from the town of Oakham. It boasts two bedrooms which include a double with an en-suite and a twin/ double room with en-suite. The property...
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This detached retreat is three miles from the Rutland town of Oakham and is able to sleep six people in three bedrooms.Wing is placed three miles from the East Midlands town of Oakham. Its three bedrooms are made up of a double with an en-suite, a further double and a twin/double room, along with a...
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Rutland Bed and Breakfast Cottages - Bedroom 21 / 6
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Guests have the freedom and exclusive occupation of a warm and comfortable cottage in this picturesque conservation village.Breakfast served in our own 17th Century oak beamed dining room. In the cottage kitchens an electric kettle, microwave and fridge. No children under 10 or pets.Two pubs...
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    LE15 8QS, Braunston-in-Rutland, Oakham
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    HAMBLETON, en-suite, dog-friendly, Exton1 / 31
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    A modern, ground floor retreat based near the East Midlands town of Oakham, it can sleep six people in three bedrooms.Hambleton is a stunning single-storey retreat located close to the town of Oakham in the East Midlands. It offers three bedrooms which include a double with an en-suite, a further...
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    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Grill
    • Sauna
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    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stretton lakes is situated within 120 acres of farmland in the picturesque county of Rutland. 4 luxury round log cabins are surrounded by woodland and set overlooking our fishing lakes. Our award winning 4 & 5* lodges are finished to an exceptionally high standard. Each lodge has its own private...
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    LE15 7QS, Oakham, Rutland
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
    Tranquil self-contained flat in stunning farm setting. Great Reviews1 / 10
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 October 2019
    Nestled in the woods this well appointed flat provides the ideal retreat for a relaxing break. Walking or cycling from the doorstep is highly recommended as the area has plenty...
    Reviewed 15 August 2017
    Great flat, good place to stay to see Rutland. Would definitely go back.Lovely people, dogs and not forgetting the pigs!. But no farm smells in flat.
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    About this property
    The Stables Flat is attached to our secluded farmhouse. We are surrounded by rolling fields grazed by cattle, sheep and horses. We keep pigs, ducks and hens. The house is down a quiet country lane without passing cars, apart from farm traffic. The light, airy flat has its own private entrance and...
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    LE7 9DN, Oakham, Rutland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    5* Lakeside Waterlily log cabin with Hot Tub and Sauna1 / 12
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Grill
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    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2015
    found this site on google search, beautiful quiet site, 5star cabin on side of fishing lake, large sauna and private hot tub for relaxing in. fishing was excellent all week...
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    About this property
    Stretton lakes is situated within 120 acres of farmland in the picturesque county of Rutland. 6 luxury round log cabins are surrounded by woodland and set overlooking our fishing lakes. Our award winning 4 & 5* lodges are finished to an exceptionally high standard. Each lodge has its own private...
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    LE15 7QS, Oakham, Rutland
    Cabin Holiday Rental - 1 Bedroom, 2 Bathrooms, Sleeps 2
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Central Heating
    • Washer
    • Sauna
    • DVD Player
    • Balcony
    • Hot Tub
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stretton lakes is situated within 120 acres of farmland in the picturesque county of Rutland. 6 luxury round log cabins are surrounded by woodland and set overlooking our fishing lakes. Our award winning 4 & 5* lodges are finished to an exceptionally high standard. Each lodge has its own private...
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    LE15 7QS, Oakham, Rutland
    Cabin Holiday Rental - 1 Bedroom, 2 Bathrooms, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Located in an idyllic village amongst the glorious rolling countryside of Rutland,this delightful cottage provides the perfect base for exploring the many attractions of the local area. Sightseer’s will be spoilt for choice with many historic buildings which dot the landscape including the 12th...
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    LE15 8QU, Braunston-in-Rutland, Oakham
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    The private estate is set in 1200 acres of glorious rolling countryside,situating in the Hamlet of Gunthorpe,next to Rutland Water. There are many activities that can be enjoyed at Rutland Water,including sailing,canoeing,windsurfing,boat trips,crazy golf,fishing,rock climbing,high...
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    LE15 8BE, Manton, Oakham
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Guests have the freedom and exclusive occupation of a warm and comfortable cottage in this picturesque conservation village.Breakfast served in our own 17th Century oak beamed dining room. In the cottage kitchens an electric kettle, microwave and fridge. No children under 10 or pets.Two pubs...
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    LE15 8QS, Braunston-in-Rutland, Oakham
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This cottage is situated in the village of Wing, near the town of Uppingham Lincolnshire, and can sleep up to four people in two bedrooms.Wren Cottage is a stone-built property situated in the village of Wing, near the town of Uppingham, Lincolnshire. The property hosts two bedrooms, one double...
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    LE15 8SE, Wing, Oakham
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This detached bungalow rests in Oakham, in the East Midlands and can sleep six people in three bedrooms.12 Trent Road is a wonderful bungalow resting in the town of Oakham in Rutland, East Midlands. Within this all-ground-floor property there are three bedrooms including a king-size with an...
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    Location Information
    LE15 6HF, Oakham, Rutland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A three bedroom retreat sat three miles from Oakham in Rutland, it can sleep six people in three bedrooms.Langham is located near Oakham in Rutland. It offers three bedrooms which include a double with an en-suite, a further double and a twin/double, there is also a family bathroom, the property is...
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    Location Information
    LE15 8AH, Barnsdale, Oakham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guests have the freedom and exclusive occupation of a warm and comfortable cottage in this picturesque conservation village.Breakfast served in our own 17th Century oak beamed dining room. In the cottage kitchens an electric kettle, microwave and fridge. No children under 10 or pets.Two pubs...
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    Location Information
    LE15 8QS, Braunston-in-Rutland, Oakham
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guests have the freedom and exclusive occupation of a warm and comfortable cottage in this picturesque conservation village.Breakfast served in our own 17th Century oak beamed dining room. In the cottage kitchens an electric kettle, microwave and fridge. No children under 10 or pets.Two pubs...
    View all property information
    Location Information
    LE15 8QS, Braunston-in-Rutland, Oakham
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
    Check-in Check-out
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    Amenities & Details
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guests have the freedom and exclusive occupation of a warm and comfortable cottage in this picturesque conservation village.Breakfast served in our own 17th Century oak beamed dining room. In the cottage kitchens an electric kettle, microwave and fridge. No children under 10 or pets.Two pubs...
    View all property information
    Location Information
    LE15 8QS, Braunston-in-Rutland, Oakham
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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