Photo by Jules & Jenny

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Our top choices for Uppingham holiday homes

1. Thyme Cottage Bulwick | Cosy 2-Bed Village Stay

Thyme Cottage Bulwick | Cosy 2-Bed Village Stay
North Northamptonshire
10.0 out of 10, Exceptional, (1 review)
"A great property and a very easy drive to Burghley Horse Trials which was the purpose of our visit. Directly next to a great pub and a property that I would recommend. It might be a bit tight for 3 adults because the living area is small and the stairs are very steep which could cause difficulties for older people or very young children but we really enjoyed our stay and would otherwise recommend."
United States
Gaynor J.
The price is £194
includes taxes & fees
10 Nov - 11 Nov
Thyme Cottage Bulwick | Cosy 2-Bed Village Stay

2. Manor View

Manor View
3.5 star property
Oakham
The price is £402
includes taxes & fees
14 Nov - 15 Nov
Manor View

3. Rutland Cottage, Ketton by Belmont Places

Rutland Cottage, Ketton by Belmont Places
Ketton
The price is £217
includes taxes & fees
10 Nov - 11 Nov
Rutland Cottage, Ketton by Belmont Places

4. Bramble House, Stamford

Bramble House, Stamford
Stamford
The price is £167
includes taxes & fees
20 Nov - 21 Nov
Bramble House, Stamford

5. 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 £212
includes taxes & fees
15 Nov - 16 Nov
Rose Cottage, 2 en suites, log burner, EV charger, enclosed garden, in Rutland.

6. Southview Terrace, 3 bedroom, Stamford by Belmont Places

Southview Terrace, 3 bedroom, Stamford by Belmont Places
Lincolnshire
10.0 out of 10, Exceptional, (1 review)
"The place was clean and modern and had everything we needed. The beds were comfortable and the linens all top notch.This was a great place to stay and we’ll stay again sometime without a second thoughtIt is close to downtown Stamford and the neighborhood is great for walking"
United States
Bruce W.
The price is £240
includes taxes & fees
30 Nov - 1 Dec
Southview Terrace, 3 bedroom, Stamford by Belmont Places

7. Fallow Cottage - 3 bedroom, Stamford centre

Fallow Cottage - 3 bedroom, Stamford centre
Lincolnshire
4.0 out of 10, (1 review)
"The property is OK if you plan to stay for a day or two. We stayed for a month and found it too small and too cluttered. It almost felt as if the owner had moved out the day before with lots of ‘stuff’ (food etc) in cupboards!There is only one bathroom/toilet on the ground floor only and the stairs are very tight and quite steep with bannisters that are loose.It is also right on the busy street and therefore very noisy from traffic.It is however in a great location with Stamford shops/pubs...
United States
P H.
The price is £209
includes taxes & fees
10 Nov - 11 Nov
Fallow Cottage - 3 bedroom, Stamford centre

8. Wothorpe House, Stamford Centre by Belmont Places

Wothorpe House, Stamford Centre by Belmont Places
Lincolnshire
10.0 out of 10, Exceptional, (1 review)
"A fantastic property in the heart of Stamford. Plenty of space and a lovely large garden. The property is only a 12 minute walk from the high street and even closer to the park and river. A very pleasant stay, would absolutely recommend."
United States
Anonymous traveller
The price is £313
includes taxes & fees
10 Nov - 11 Nov
Wothorpe House, Stamford Centre by Belmont Places

9. NEW Luxury Countryside Retreat for Family and Friends

NEW Luxury Countryside Retreat for Family and Friends
Clipston
10.0 out of 10, Exceptional, (33 reviews)
"Fabulous property."
Canada
Nic L.
The price is £222
includes taxes & fees
12 Nov - 13 Nov
NEW Luxury Countryside Retreat for Family and Friends

10. Kettering - House - Stay 8 - Parking - Garden

Kettering - House - Stay 8 - Parking - Garden
4.0 star property
Kettering
10.0 out of 10, Exceptional, (1 review)
"love this property. Always stay here when in the area. Quiet residential area with space for 2 cars on private drive. "
United Kingdom
Tom
The price is £303
includes taxes & fees
24 Nov - 25 Nov
Kettering - House - Stay 8 - Parking - Garden

11. Stylish 3-Bed with Smart TVs, Parking & Workspace

Stylish 3-Bed with Smart TVs, Parking & Workspace
Kettering
The price is £260
includes taxes & fees
23 Nov - 24 Nov
Stylish 3-Bed with Smart TVs, Parking & Workspace

12. House-Sleeps 8 -Parking-Garden

House-Sleeps 8 -Parking-Garden
Barton Seagrave
10.0 out of 10, Exceptional, (1 review)
"My son and I visited with some friends and their kids for 1 night over the may bank holiday. The house has plenty of space and the kids enjoyed exploring and picking their rooms. It's close to a Budgins and fish and chip shop so food was easily available. We went to Stanwick Lakes which is only 20mins drive away and a giant free adventure play area."
United Kingdom
Natalie B.
The price is £278
includes taxes & fees
11 Nov - 12 Nov
House-Sleeps 8 -Parking-Garden

13. Entire Excellent Property on Mountcastle Road, Leicester

Entire Excellent Property on Mountcastle Road, Leicester
Leicester
The price is £156
includes taxes & fees
10 Nov - 11 Nov
Entire Excellent Property on Mountcastle Road, Leicester

14. Boutique 2Bed Townhouse | Bourne Centre | Sleeps 4

Boutique 2Bed Townhouse | Bourne Centre | Sleeps 4
Bourne
The price is £176
includes taxes & fees
30 Nov - 1 Dec
Boutique 2Bed Townhouse | Bourne Centre | Sleeps 4

15. The Old Bakery. Deluxe converted barn.

The Old Bakery. Deluxe converted barn.
Stilton
The price is £107
includes taxes & fees
11 Nov - 12 Nov
The Old Bakery. Deluxe converted barn.

16. Melton Mowbray Luxury Stay

Melton Mowbray Luxury Stay
Melton Mowbray
The price is £229
includes taxes & fees
20 Nov - 21 Nov
Melton Mowbray Luxury Stay

17. Quaint 2-bedroom house in Leicester for a cozy getaway

Quaint 2-bedroom house in Leicester for a cozy getaway
Leicester
The price is £152
includes taxes & fees
11 Nov - 12 Nov
Quaint 2-bedroom house in Leicester for a cozy getaway

18. The Studio - A Unique and Luxurious Country Barn Conversion.

The Studio - A Unique and Luxurious Country Barn Conversion.
Castle Bytham
The price is £338
includes taxes & fees
12 Nov - 13 Nov
The Studio - A Unique and Luxurious Country Barn Conversion.

19. COZY,LUXURY AND STYLISH TWO BEDROOM HOME with Garden, Gym & Work spaces.

COZY,LUXURY AND STYLISH TWO BEDROOM HOME with Garden, Gym & Work spaces.
Leicester
9.0 out of 10, Wonderful, (2 reviews)
"We like to stay it’s very peacefully and nice we spent very good time."
United Kingdom
Yash
The price is £151
includes taxes & fees
11 Nov - 12 Nov
COZY,LUXURY AND STYLISH TWO BEDROOM HOME with Garden, Gym & Work spaces.

20. 3 Bed House - Sleeps 4 - Parking - Wifi

3 Bed House - Sleeps 4 - Parking - Wifi
3.0 star property
Rushden
The price is £150
includes taxes & fees
11 Nov - 12 Nov
3 Bed House - Sleeps 4 - Parking - Wifi
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.

Learn more about Uppingham

These charming market towns showcase historic architecture with Uppingham's antique shops and Oakham's impressive castle featuring a unique collection of ceremonial horseshoes. Explore the quaint independent boutiques and tea rooms, then visit nearby Rutland Water for sailing, cycling, and spotting ospreys at the nature reserve.

A church interior with wooden pews, a central aisle, and a stained glass window.
Photo by Jules & Jenny
Open Photo by Jules & Jenny

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