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Uppingham Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Uppingham vacation rentals

A modern kitchen with a built-in stove, wooden cabinets, and a window.

1. Luxury Shepherd Hut situated on a private 30 acre estate in the heart of Rutland

Luxury Shepherd Hut situated on a private 30 acre estate in the heart of Rutland
Ketton
10.0 out of 10, Exceptional, (1 review)
"Absolutely amazing stay at the Rabbit Hut! Host was amazing and the Hut was the perfect peaceful break we needed. Will be back soon!"
United States
Maxine B.
The price is ￥31,728
￥32,997 total
includes taxes & fees
Dec 13 - Dec 14
Luxury Shepherd Hut situated on a private 30 acre estate in the heart of Rutland
A modern kitchen with a central island, a dining area with a bench, and a skylight above.

2. Gardeners Cottage

Gardeners Cottage
2.5 star property
Oakham
The price is ￥359,307
￥431,168 total
includes taxes & fees
Nov 17 - Nov 18
Gardeners Cottage
A cozy living room with a sofa, teal cushions, a wooden dining table with chairs, a kitchen in the background, and a brick wall with a clock.

3. 2 bedroom accommodation in Oakham

2 bedroom accommodation in Oakham
Oakham
8.0 out of 10, Very good, (4 reviews)
"great location on the edge of Oakham, easy walking to shops, cafes, pubs etc. Road parking was fine but the road is quite narrow with cars parked up both sides. lots of outdoor activities at Rutland water. Only 20 minute drive from the historic town of Stamford.plenty of hot water and house lovely and warm."
United States
Margaret Watters
The price is ￥41,777
￥41,777 total
includes taxes & fees
Nov 15 - Nov 16
2 bedroom accommodation in Oakham
A historic building with a corner turret, large windows, and a sign indicating a bicycle parking zone.

4. The Gresham Aparthotel

The Gresham Aparthotel
3.5 star property
Leicester City Centre
9.0 out of 10, Wonderful, (500 reviews)
"Better than a small hotel room, staff were excellent. Could have stayed much longer!"
Canada
James
The price is ￥9,463
￥11,356 total
includes taxes & fees
Nov 22 - Nov 23
The Gresham Aparthotel
A modern building with a brick facade, solar panels on the roof, and a well-maintained lawn with a pathway.

5. Ascot House

Ascot House
4.0 star property
Peterborough
9.2 out of 10, Wonderful, (45 reviews)
"Clean room, nice space, night time lady at reception was super lovely"
United Kingdom
Raquel
The price is ￥14,764
￥17,717 total
includes taxes & fees
Dec 10 - Dec 11
Ascot House
A dark blue door with a white handle and a decorative glass panel above it.

6. Robin's Nest, your home from home

Robin's Nest, your home from home
Wilbarston
8.0 out of 10, Very good, (1 review)
"Host there to welcome us when we arrived. He helped to carry in the luggage and showed us how the hot water and heating worked. Amenities were ideal with breakfast food items included plus a bottle of Prosecco and shortbread as a thoughtful Christmas gift. The property had been decorated for Christmas - another kind and thoughtful touch. The property was spotlessly clean and had everything that we needed. The bed was extremely comfortable. Thank you to the hosts. "
United Kingdom
Angela W.
The price is ￥18,662
￥20,783 total
includes taxes & fees
Nov 15 - Nov 16
Robin's Nest, your home from home
A bedroom with a bed, a nightstand, a lamp, a window, and a view of the sky.

7. 1 Bed Flat - Sleeps 2 - Pets - Parking - Wifi

1 Bed Flat - Sleeps 2 - Pets - Parking - Wifi
3.0 star property
Kettering
The price is ￥13,043
￥22,014 total
includes taxes & fees
Nov 14 - Nov 15
1 Bed Flat - Sleeps 2 - Pets - Parking - Wifi
A living room with a sofa, a lamp, a radiator, and a window with plants.

8. Bramble House, Stamford

Bramble House, Stamford
Stamford
The price is ￥24,748
￥35,324 total
includes taxes & fees
Dec 14 - Dec 15
Bramble House, Stamford
A stone wall with pink flowers, a stone building with windows, and a bench.

9. Rose Cottage, 2 en suites, log burner, EV charger, enclosed garden, in Rutland.

Rose Cottage, 2 en suites, log burner, EV charger, enclosed garden, in Rutland.
Great Casterton
The price is ￥25,872
￥45,170 total
includes taxes & fees
Nov 16 - Nov 17
Rose Cottage, 2 en suites, log burner, EV charger, enclosed garden, in Rutland.
A wicker table and chairs on an outdoor patio with a view of a sunset over a body of water.

10. Bijou boutique country room, private terrace with beautiful countryside views.

Bijou boutique country room, private terrace with beautiful countryside views.
Corby Glen
9.4 out of 10, Exceptional, (3 reviews)
"This is exactly what we needed. Brilliant host, lots of personal touches in the accommodation, we will be back!"
United Kingdom
Laura
The price is ￥20,941
￥23,056 total
includes taxes & fees
Nov 16 - Nov 17
Bijou boutique country room, private terrace with beautiful countryside views.
A quaint cottage with a white door, a small window, and a sign reading "Bennett's Cottage".

11. Bennett's Cottage

Bennett's Cottage
3.5 star property
Oakham
10.0 out of 10, Exceptional, (1 review)
"Lovely property and the local support staff were close by and very friendly"
United Kingdom
Matthew
The price is ￥67,331
￥80,797 total
includes taxes & fees
Nov 24 - Nov 25
Bennett's Cottage
Interior detail

12. Park View

Park View
2.0 star property
Leicester
8.4 out of 10, Very good, (17 reviews)
"I enjoyed my stay"
United Kingdom
Eliu
The price is ￥7,714
￥9,257 total
includes taxes & fees
Nov 15 - Nov 16
Park View
A patio with a grill, outdoor seating, and a view of a field.

13. The Cottage · Luxury Romantic Retreat in Idyllic Rural Location

The Cottage · Luxury Romantic Retreat in Idyllic Rural Location
Clipston
10.0 out of 10, Exceptional, (22 reviews)
"Clean and comfy interior - really appreciated the small gestures from the owner such as a special anniversary touch as requested, sourdough bread and other items for breakfast."
United Kingdom
Mashkoor A.
The price is ￥30,882
￥43,362 total
includes taxes & fees
Nov 16 - Nov 17
The Cottage · Luxury Romantic Retreat in Idyllic Rural Location
Room

14. THE BRIGHT | Exclusive Boutique Residence in the Heart of Stamford

THE BRIGHT | Exclusive Boutique Residence in the Heart of Stamford
Stamford
The price is ￥41,881
￥45,477 total
includes taxes & fees
Nov 24 - Nov 25
THE BRIGHT | Exclusive Boutique Residence in the Heart of Stamford
A dining area with a round table, two chairs, a pendant light, and a kitchen with green cabinets in the background.

15. THE MOODY | Luxury Grade II Listed Retreat in Historic Stamford

THE MOODY | Luxury Grade II Listed Retreat in Historic Stamford
Stamford
The price is ￥41,881
￥45,477 total
includes taxes & fees
Nov 24 - Nov 25
THE MOODY | Luxury Grade II Listed Retreat in Historic Stamford
Room

16. Private Studio with parking near A14

Private Studio with parking near A14
Burton Latimer
The price is ￥12,724
￥12,724 total
includes taxes & fees
Dec 3 - Dec 4
Private Studio with parking near A14
A modern living room with a large window, a sofa, and a dining area.

17. 14 Acres

14 Acres
5.0 star property
Market Harborough
The price is ￥42,718
￥51,261 total
includes taxes & fees
Dec 9 - Dec 10
14 Acres
A modern kitchen with grey cabinets, a central island, and a dining area with wicker chairs.

18. Vine Cottage - 3 Bedroom, Stamford Centre.

Vine Cottage - 3 Bedroom, Stamford Centre.
Lincolnshire
10.0 out of 10, Exceptional, (1 review)
"Excellent all round! "
United Kingdom
Jerry B.
Vine Cottage - 3 Bedroom, Stamford Centre.
A modern living room with a grey sofa, a patterned ottoman, a small table, and a window with curtains.

19. 1-bed Apartment, Sleeps 4 Near Orton Wood

1-bed Apartment, Sleeps 4 Near Orton Wood
2.5 star property
Peterborough
The price is ￥13,702
￥16,443 total
includes taxes & fees
Nov 23 - Nov 24
1-bed Apartment, Sleeps 4 Near Orton Wood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Uppingham Hotel Reviews

Rushton Hall Hotel & SPA

Rushton Hall Hotel & SPA

10/10 Excellent
"Stay there often & it never disappoints"
Ann 1-night trip
Posted 9 hours ago
Rushton Hall Hotel & SPA

Find out more about Uppingham

Search for holiday rentals in Uppingham on Expedia! You can easily find your home rentals, villas, holiday apartments in Uppingham using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Uppingham?

Yes, we have vacation rentals close to top local attractions in Uppingham, or you can choose a more remote option if you're looking for a relaxing stay. Our travelers say Uppingham has a good selection of bars and the restaurants. Make sure you have time to check out the coffeehouses while you're in the area.

What are some of the best vacation rentals in Uppingham?

3 Bed House - Sleeps 6 - Parking - Wifi: This vacation home rental outside of Uppingham comes with free WiFi so you can feel at home during your trip. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Uppingham?

Expedia has 3 vacation rentals for your stay in Uppingham.

What can I see and do in Uppingham?

Enjoy the area's cultural attractions such as Corby Heritage Centre, or get outdoors into nature at a spot like Rutland Water Nature Reserve. In the larger area, you’ll find Lyddington Bede House and Rutland Water Country Park.

What are vacation rentals like in Uppingham?

Vacation rentals are privately owned properties you can reserve for several days or more in Uppingham. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a family trip.