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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Uppingham cottages

A two-story house with a brick exterior and a white front door. There are potted plants and a bench outside.

1. 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 AED 1,557
AED 1,869 total
includes taxes & fees
15 Nov - 16 Nov
Bennett's Cottage
A brick house with a tiled roof, white windows, and a visible gutter system.

2. 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 AED 966
AED 966 total
includes taxes & fees
12 Nov - 13 Nov
2 bedroom accommodation in Oakham
A patio with a grill, outdoor seating, and a view of a field.

3. 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 AED 716
AED 1,005 total
includes taxes & fees
9 Nov - 10 Nov
The Cottage · Luxury Romantic Retreat in Idyllic Rural Location
A red door with a white window, a brick building with ivy, and a clear sky.

4. 2 bedroom accommodation in Market Overton

2 bedroom accommodation in Market Overton
Market Overton
10.0 out of 10, Exceptional, (1 review)
"Wonderful peaceful cottage, as a family weve had a much needed break, and were able to explore our family history in surrounding villages. Very much recommended....."
United Kingdom
Dewyl1
2 bedroom accommodation in Market Overton
A small stone building with a tiled roof, a wooden fence, and a paved road.

5. 1 bedroom accommodation in Sproxton

1 bedroom accommodation in Sproxton
Sproxton
10.0 out of 10, Exceptional, (9 reviews)
"A lovely cottage with some quirky touches which made it a very special and unique. Perfect location for dog walking from the door step. Always looked forward to returning to the cottage after a day out to relax and chill .Would happily recommend."
United States
Paul Taylor
The price is AED 1,437
AED 1,437 total
includes taxes & fees
22 Nov - 23 Nov
1 bedroom accommodation in Sproxton
A stone house with a traditional design, featuring a central door, multiple windows, and a small garden area.

6. Charming cottage near lovely Stamford with cosy open fire and a rural location.

Charming cottage near lovely Stamford with cosy open fire and a rural location.
Stamford, near Easton-on-the-Hill
6.0 out of 10, (2 reviews)
"A very comfortable cottage. Excellent enclosed garden if you have a dog and great walks within 200 yards of the cottage to the 'deeps' or beyond to at least two longer distance paths. Stamford is ten minutes away and if yoir visiting family in the area its a great base with good road links.We had our break at half term (February) the cottage is well heated with a log burning fire!....we bought extra logs from Morrisons in Stamford (about £8 a bag).Bob and Sarah provided a great welcome pack...
United States
Bob Banks
The price is AED 1,731
AED 1,731 total
includes taxes & fees
10 Nov - 11 Nov
Charming cottage near lovely Stamford with cosy open fire and a rural location.
A red brick building with a white door, a window with a hanging flower basket, and a small evergreen tree in front.

7. 5A Waterfall Way

5A Waterfall Way
3.5 star property
Market Harborough
10.0 out of 10, Exceptional, (2 reviews)
"Loverly little apartment in a loverly village - pub next door to always helps for a refresher"
United Kingdom
Lewis
The price is AED 1,428
AED 1,714 total
includes taxes & fees
18 Nov - 19 Nov
5A Waterfall Way
A stone house with a gravel driveway, a small garden, and a wooden deck.

8. 9 Rectory Lane

9 Rectory Lane
3.0 star property
Oakham
The price is AED 1,845
AED 2,214 total
includes taxes & fees
1 Dec - 2 Dec
9 Rectory Lane
A stone cottage with a red-tiled roof, a green door, and a small garden area with a planter and a pathway.

9. Bumble Bee

Bumble Bee
3.0 star property
Oakham
5.0 out of 10, (2 reviews)
"There is no parking … How you can advertise bumping up a high kerb onto the pavement to park is wrong , we would not of booked this property … Only suitable for 2 people not 4 Needs a good deep clean "
United Kingdom
Johann
The price is AED 1,515
AED 1,818 total
includes taxes & fees
11 Nov - 12 Nov
Bumble Bee
A red brick house with a pitched roof, a chimney, and a small porch with a door.

10. Gardeners Cottage

Gardeners Cottage
2.5 star property
Oakham
The price is AED 8,331
AED 9,997 total
includes taxes & fees
11 Nov - 12 Nov
Gardeners Cottage
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

11. Bee Hive

Bee Hive
3.0 star property
Oakham
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved every thing about our stay at bee hive! The perfect place to meet up with very good friends. The hot tub was great fun, food on site delicious- we adored the calm quiet atmosphere and gorgeous view from our veranda. The entire place was so clean too..! Could not fault a thing!"
United Kingdom
Tina
The price is AED 2,655
AED 3,186 total
includes taxes & fees
13 Nov - 14 Nov
Bee Hive
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

12. Squirrel's Nest

Squirrel's Nest
3.0 star property
Oakham
10.0 out of 10, Exceptional, (1 review)
"Lovely property. Very clean & staff were very helpful. Wood fired hot tub maybe not ideal & you have to buy your own wood after night one (b&m much cheaper than buying it there). But was good it was lit & warmed up for us on arrival. A very enjoyable stay, although we left a lot of food & drink in the fridge & we were almost home by the time we realised 😞"
United Kingdom
Dennis
The price is AED 2,710
AED 3,252 total
includes taxes & fees
14 Nov - 15 Nov
Squirrel's Nest
A patio area with a wooden table and chairs, surrounded by a brick wall and a wooden fence.

13. Stables Cottage

Stables Cottage
3.0 star property
Leicester
The price is AED 2,641
AED 3,170 total
includes taxes & fees
14 Nov - 15 Nov
Stables Cottage
A patio with a table and chairs, a brick wall, and a view of a green field.

14. Grooms Cottage

Grooms Cottage
3.0 star property
Leicester
The price is AED 2,298
AED 2,758 total
includes taxes & fees
11 Nov - 12 Nov
Grooms Cottage
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

15. Rabbit Hole

Rabbit Hole
3.0 star property
Oakham
The price is AED 4,065
AED 4,878 total
includes taxes & fees
15 Nov - 16 Nov
Rabbit Hole
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

16. Otter's View

Otter's View
3.0 star property
Oakham
The price is AED 3,159
AED 3,790 total
includes taxes & fees
11 Nov - 12 Nov
Otter's View
A traditional stone building with a sign reading "THE MALTINGS".

17. The Hideout

The Hideout
3.0 star property
Oakham
6.0 out of 10, (1 review)
The price is AED 2,234
AED 2,681 total
includes taxes & fees
15 Nov - 16 Nov
The Hideout
A brick building with a triangular roof, a small window, and a gated entrance.

18. Farm View House

Farm View House
3.0 star property
Melton Mowbray
The price is AED 3,058
AED 3,669 total
includes taxes & fees
16 Nov - 17 Nov
Farm View House
A riverside view of a quaint inn with outdoor seating and a stone building.

19. Buckingham House

Buckingham House
3.0 star property
Oakham
The price is AED 3,328
AED 3,993 total
includes taxes & fees
16 Nov - 17 Nov
Buckingham House
A stone building with a tiled roof, a sign for 'Brook Bond Tea', and outdoor seating.

20. The Walnut Room - Windmill Country Retreats

The Walnut Room - Windmill Country Retreats
2.0 star property
Melton Mowbray
The price is AED 1,501
AED 1,802 total
includes taxes & fees
14 Nov - 15 Nov
The Walnut Room - Windmill Country Retreats
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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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.

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

Frequently Asked Questions

How much do cottages in Uppingham cost?

Prepare to pay between AED 716 and AED 8,331 per night for cottages in Uppingham. No matter your budget, a wonderful stay is just a few clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What are the best cottages in Uppingham?

A guest favorite is The Windmill. Get comfortable at this 3.5-star stay which offers individually decorated rooms and WiFi. Ashwell is another popular option to look into. Unpack your suitcases at this 3.5-star cottage and you'll have access to conveniences such as individually decorated rooms and a garden. You can pick from multiple cottages in Uppingham with a total average guest review rating of 9.4.

How many cottages are there in Uppingham?

Enjoy reconnecting with nature in one of the cottages waiting for you in Uppingham. To help you choose your ideal place, take advantage of our filters to search for must-have amenities.

Why book your cottage in Uppingham with Expedia?

Reserving a cottage in Uppingham is as simple as entering your travel dates and selecting your ideal place for a vacation in the outdoors. From luxurious retreats to inexpensive stays and cottages that include amenities like laundry facilities, Expedia has something for all traveler styles. As for the best offers around? We have them too!

How can I find cheap cottages in Uppingham?

The quickest way to track down cheap cottages in Uppingham is with Expedia's filter tool. Narrow your search results by budget, star rating and amenities to take advantage of awesome prices in just a few clicks.