
Vacation rentals in Uppingham
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Top-rated vacation rentals in Uppingham
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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.

The Hayloft: Popular Hideaway - Sleeps 3.
After our storming success for 6 years with our cosy Hayloft Apartment, we have totally refitted the bathroom, installed a brand new kitchen and added a single bedroom / study. Fresh paint, blinds and carpets throughout! Guests have dedicated parking [Now with EV Charging] a private patio for sunny breakfasts, lunches or sundowners. Home-cooked ready meals are available in the fridge or freezer when you arrive. Message when you book and we can supply details. The Welcome pack's a big hit.

Beautiful and Quaint Converted Stable in Rutland
This Grade-2 Listed, self-contained, dog-friendly cottage is the perfect hideaway for a couple looking to enjoy the beautiful Rutland countryside. Ketton is only a few minutes drive from the beautiful town of Stamford, or Rutland Water with its stunning views and local Ospreys. Oakham is also a short drive away. There's a Camra award-winning pub a few minutes walk away and plenty of circular walks in the surrounding countryside, from the accommodation or further afield, to work up a thirst.

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

Luxury apartment with outstanding views
We created a self catering studio apartment from our hay loft during the lockdown of 2020. In the heart of the Welland Valley in Leicestershire there are are wonderful views up the hill to Nevill Holt (home of the Nevill Holt Opera Festival) and from the sofa you will be able to watch the sun setting behind the hill. Many miles of footpaths on the doorstep. There is a heated pool open May-Sept and a tennis court. Please ask us regarding access. Check out our guidebook for things to do

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.

Oak Tree Annexe
Oak Tree Annexe is set in a secluded and secure walled garden. You can park for free directly outside the house and will be staying in one of Rutland’s most desirable villages. Set on the fabulous cycle route around the water and with access to great walks directly from the house or a short drive away it’s a perfect location for exploring Rutland. Our village pub is a 3 minute stroll, serves food 7 days a week and offers our guests a 10% discount on their meals.

Quiet Rural Chapel Conversion (Architectural Gem)
Stylish & unique, self- contained historic Chapel conversion overlooking stunning scenery, (Chater Valley) tucked away at the edge of Conservation Village, 5 min drive from R.Water. Private. Sleeps 4 1 king-size & 1 small DBL Kids 8+ welcome Park free outside Quiet & very rural. Grade ii Listed. Modern interior feat. in "Living Etc" , on TV & won a local design award Helpful owners next door Completely OPEN PLAN INTERNAL WALLS ONLY AROUND BATHROOM

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.

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.

Mayfield - 1 bedroom annexe flat
Kick back and relax in this calm, stylish space. Private annexe flat with its own access. Open plan kitchen and living area. Separate dining area. 1 bedroom with zip link beds, can either be twin or superking. Bathroom with shower. Hallway. Access to washing machine, tumble dryer and clothes airer on request. Lockable storage for push bikes on request. Outside patio area.

Rural accommodation- peace and quiet
Beech Barn is a very comfortable and peaceful space in a lovely rural setting with superb views and yet walking distance to a great pub with restaurant and a village store. The room has a private patio, Wifi, Smart tv, seating area, en suite shower as well as an area for tea and coffee.
Popular amenities for Uppingham vacation rentals
Other great vacation rentals in Uppingham

Box Barn - Stylish Accommodation in Rutland

Beautiful Conversion in Rutland Countryside

No. 34b

The Old Bookshop

Healey House The Annex

The little village hideout

Private entrance contemporary bedroom with ensuite

Charming cottage in picturesque country village
Quick stats about vacation rentals in Uppingham
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Frequently Asked Questions
Do house rentals in Uppingham have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Uppingham. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Uppingham?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Uppingham?
Experience the best of Uppingham with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Uppingham have wifi?
Absolutely! We offer over 10 house rentals with wifi in Uppingham. Enjoy a tailored experience with all the comforts you desire.
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- Lincoln Castle
- Wicksteed Park
- Coventry Cathedral
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- Kettle's Yard
- Rufford Park Golf and Country Club
- Leamington & County Golf Club
- The Fitzwilliam Museum
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- National Justice Museum