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Holiday houses in Uppingham

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Top-rated holiday rentals in Uppingham

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Top Guest favourite
A rustic wooden sign is mounted on a metal bracket, displaying the name 'St. James's Cottage.' The sign is attached to a stone wall with visible texture, and utility lines are present in the background.
Condo in Gretton
4.98 out of 5 average rating, 414 reviews

St James's Cottage – Gretton

An independent, first floor, apartment in a 200yr old cottage. 1 bedroom available as superking bed or twin beds. Separate living room with kitchenette, combination microwave/oven/grill, single zone hob, toaster, kettle and full size fridge. Bathroom with shower. Free WiFi. Private, off road parking outside cottage. Secure garage space available upon request, for locking up bicycles, fishing tackle, golf clubs etc. Set in a lovely, quiet, village with two pubs & coffee shop in walking distance.

Top Guest favourite
Townhouse in Manton
4.99 out of 5 average rating, 166 reviews

Entire House - Osprey Cottage, Manton in Rutland.

Osprey Cottage in Manton is a beautifully presented end terrace property which sleeps 4 guests. One bedroom with a king size bed, a second bedroom that can be configured either as single beds (2’6” wide) or a king, and a stylish bathroom. Finished in a contemporary style with modern facilities including Wi-Fi(74mb), TV, a well-equipped kitchen with dishwasher and washing machine. The fenced garden has a shed and we welcome well-behaved dogs(£20 charge applies). Bedding and towels are included

Top Guest favourite
A spacious lounge features a comfortable grey sectional sofa adorned with decorative pillows. A neutral rug anchors the seating area, while natural light streams through a large window dressed with sheer curtains. A modern chandelier hangs above, and a decorative mirror adds depth to the room.
Condo in Uppingham
4.98 out of 5 average rating, 112 reviews

Elegant 3 bed High Street apartment in Uppingham

A spacious and elegant 3 bed apartment on the middle floor of a Grade II listed Georgian house in the heart of historic Uppingham. This spacious home has been lovingly restored and is stylishly decorated and furnished to a high standard. 2 comfy double beds and 1 single bed with good quality mattresses. A spacious lounge. Full kitchen , table and chairs for 5, dishwasher and microwave and starter essentials provided, tea & coffee, wash up liquid, dishwasher tabs etc. FREE HIGH SPEED BT Wi-Fi

Top Guest favourite
A spacious outdoor dining area is set under a wooden pergola, adorned with colorful bunting. A large table is surrounded by eight chairs, with pink glasses and flower arrangements accenting the table. Guests are seen enjoying a barbecue in the scenic countryside backdrop.
Barn in Hallaton
4.97 out of 5 average rating, 126 reviews

Unique Countryside hideaway

Unique rural retreat perched on a hill in open countryside with breathtaking views. The Retreat is a self-contained 3 bedroom home adjacent to our barn conversion in 13 acres. The barn was converted by ourselves over two levels - one ground floor and one underground (don't worry it is very light and airy on the lower floor!) The perfect place for a countryside getaway to totally relax and unwind. Great walking and cycling on your doorstep or just switch off, chill out and enjoy the space.

Top Guest favourite
The exterior of a stone barn conversion features a distinct pitched roof and a charming facade. The building is marked by weathered stonework and traditional details, including a chimney and a welcoming entrance, set against a clear blue sky.
Cottage in Empingham
4.99 out of 5 average rating, 180 reviews

Primrose Hall Holiday Cottage Rutland

Primrose Hall is a beautifully renovated, Grade 2 listed stone barn conversion. It is ideally situated in the Rutland village of Empingham, within walking distance of Rutland Water’s North Shore. Empingham nestles in the Gwash Valley, equidistant from the charming Georgian town of Stamford, and Rutland’s county town, Oakham. The village has a shop, pub, medical centre, and an antique shop just 250m away. The local area also benefits from many other very good pubs, restaurants and cafes.

Guest favourite
An open plan suite features a king-sized bed with a plush headboard, complemented by a decorative quilt. A vintage grey wardrobe stands beside the freestanding bathtub, which is positioned near a large wall clock. Soft lighting enhances the serene atmosphere of the space.
Apartment in Rutland
4.86 out of 5 average rating, 299 reviews

Clock Cottage Self contained Rutland Rural Retreat

Clock Cottage is a self contained open plan suite located on the ground floor with garden views located within a characterful rural village within a 5 minute drive from Rutland water. The suite is open plan and includes a king sized bed, comfy living area and kitchen, Nespresso coffee machine, freestanding open plan bathtub and separate bathroom and outside dining area. The living area can be used as a family/friends bedroom with the use of a fold out sofa bed. Ideal for a couple.

Guest favourite
Condo in Uppingham
4.91 out of 5 average rating, 192 reviews

Comfy Modern APT - Sleeps 4

Located in the centre of the Historic Market Town of Uppingham. Based in is heart of the small county of Rutland. This apartment is a stones throw away to the gorgeous town centre, with markets every Friday, great places to eat and drink and some really cute little shops. A quick 10 minute drive to another Market Town of Oakham and not far from Rutland Water where you can enjoy some beautiful scenic walks. The apartment offers an allocated parking space and communal paved garden.

Top Guest favourite
The kitchen features a double Belfast sink and handcrafted cabinetry, highlighted by warm, natural light filtering through the window. Exposed ceiling beams complement the neutral tones of the stylish design, while a potted plant adds a touch of greenery to the inviting space.
Condo in Uppingham
4.91 out of 5 average rating, 117 reviews

Central Character/Contemporary Apartment

Set within walking distance to Uppingham’s bustling town centre is this stunning central ground floor apartment full of character and original features creating an ultimate holiday experience. Guests will enjoy two spacious double bedrooms, built in wardrobe, hand crafted breakfast kitchen, exceptional shower room, subtle design touches and beautiful courtyard garden. Free parking is available 2-3min walk away from the property. There is also 2hrs free parking to the front.

Top Guest favourite
Guest suite in Middleton
4.92 out of 5 average rating, 106 reviews

One bed ensuite Studio/Apartment with free parking

Free parking right outside Studio Apartment. Just one miles from Corby so ideal accommodation for a Contractor. Contact us for weekly or monthly dates. Contemporary designed spacious ensuite double bedroom with private shower room above an Oak Garage. Facilities available fridge/freezer, kettle, Microwave, Nespresso pod coffee machine, cutlery and crockery. TV and WiFi. Please note - stairs up to room which is sited above a garage. No hairdryer is supplied.

Top Guest favourite
The spacious kitchen is equipped with a large island unit and features light grey cabinetry. A range cooker and a dishwasher are included, alongside open shelves displaying dinnerware. Natural light enters through a nearby window, illuminating the warm wooden floor.
Home in Uppingham
4.95 out of 5 average rating, 156 reviews

36 High Street West -two bedroom luxury terrace

The property is set in the heart of this popular market town opposite the historic Uppingham School. It is perfect for any visitors to the school and is a short walk from the town's amenities which include a good range of independent shops and eating establishments. It is a spacious two bedroom house with a large, beautiful kitchen/ dining space and sheltered walled courtyard garden. The house has been decorated and furnished to a high standard.

Top Guest favourite
A charming living space features exposed brick walls, accented by elegant mirrors. A spacious bed with soft pillows is flanked by bedside tables, and a cozy sofa is complemented by a bright yellow cushion. Light spills in from a window with muted curtains.
Barn in Uppingham
4.93 out of 5 average rating, 101 reviews

Topiary Barn - Stylish Accommodation in Rutland

Stylish holiday accommodation located in a beautiful topiary garden behind Uppingham Antiques Centre. Garden studio designed for 2 guests. In cosy living space with wood burning stove, WIFI, newly fitted kitchen and ensuite with modern interior and statement antiques located in the stunning market town of Uppingham in England's smallest county of Rutland. Within 4 miles of Rutland Water

Guest favourite
The entrance to the property is framed by lush greenery and colorful flowers, creating a vibrant and inviting exterior. A set of steps leads to two light green doors, flanked by decorative plants and pots. The original stone facade of the building adds character.
Cottage in Uppingham
4.91 out of 5 average rating, 341 reviews

Number 4, Pleasant Terrace, Uppingham, Rutland

No.4 is close to the centre of Uppingham. You’ll love No.4 because of the views over open countryside at the back whilst being within a 5 minute walk of the towns restaurants and pubs. No.4 is good for couples and business travellers. Parking is unrestricted on the road outside. Pleasant Terrace is a Cul-De-Sac so no passing traffic and it is very quiet and peaceful at night.

Popular amenities for Uppingham holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Rutland
  5. Uppingham