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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Uppingham cottages

A red brick building with a white door, a window with a hanging flower basket, and a small evergreen tree in front.

1. 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
$351 nightly
The price is $422
Oct 23 - Oct 24
Total with taxes and fees
5A Waterfall Way
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
$282 nightly
The price is $282
Oct 16 - Oct 17
Total with taxes and fees
2 bedroom accommodation in Oakham
A red door with a white window, a brick building with ivy, and a clear sky.

3. 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
$367 nightly
The price is $367
Oct 30 - Oct 31
Total with taxes and fees
2 bedroom accommodation in Market Overton
A patio with a grill, outdoor seating, and a view of a field.

4. 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.
$272 nightly
The price is $272
Nov 9 - Nov 10
Total with taxes and fees
The Cottage · Luxury Romantic Retreat in Idyllic Rural Location
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
$526 nightly
The price is $526
Oct 20 - Oct 21
Total with taxes and fees
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
$468 nightly
The price is $468
Oct 18 - Oct 19
Total with taxes and fees
Charming cottage near lovely Stamford with cosy open fire and a rural location.
A stone house with a gravel driveway, a small garden, and a wooden deck.

7. 9 Rectory Lane

9 Rectory Lane
3.0 star property
Oakham
$454 nightly
The price is $545
Nov 6 - Nov 7
Total with taxes and fees
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.

8. 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
$373 nightly
The price is $447
Oct 29 - Oct 30
Total with taxes and fees
Bumble Bee
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

9. 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
$653 nightly
The price is $784
Oct 21 - Oct 22
Total with taxes and fees
Bee Hive
A stone building with a sign reading "THE MALTINGS".

10. Flat 2, The Maltings

Flat 2, The Maltings
3.0 star property
Oakham
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful apartment, far bigger than the photos suggest. It's tastefully decorated and really well equipped. The host was friendly and helpful. Ten out of ten!"
United Kingdom
M
$569 nightly
The price is $683
Oct 24 - Oct 25
Total with taxes and fees
Flat 2, The Maltings
A patio area with a wooden table and chairs, surrounded by a brick wall and a wooden fence.

11. Stables Cottage

Stables Cottage
3.0 star property
Leicester
$650 nightly
The price is $780
Oct 19 - Oct 20
Total with taxes and fees
Stables Cottage
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
$667 nightly
The price is $800
Oct 19 - Oct 20
Total with taxes and fees
Squirrel's Nest
A patio with a table and chairs, a brick wall, and a view of a green field.

13. Grooms Cottage

Grooms Cottage
3.0 star property
Leicester
$566 nightly
The price is $679
Oct 30 - Oct 31
Total with taxes and fees
Grooms Cottage
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

14. Rabbit Hole

Rabbit Hole
3.0 star property
Oakham
$1,000 nightly
The price is $1,200
Oct 19 - Oct 20
Total with taxes and fees
Rabbit Hole
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

15. Otter's View

Otter's View
3.0 star property
Oakham
$777 nightly
The price is $933
Oct 21 - Oct 22
Total with taxes and fees
Otter's View
A red brick house with a pitched roof, a chimney, and a small porch with a door.

16. Gardeners Cottage

Gardeners Cottage
2.0 star property
Oakham
$2,050 nightly
The price is $2,460
Oct 18 - Oct 19
Total with taxes and fees
Gardeners Cottage
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)
$550 nightly
The price is $660
Oct 27 - Oct 28
Total with taxes and fees
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
$753 nightly
The price is $903
Oct 18 - Oct 19
Total with taxes and fees
Farm View House
A stone building with a tiled roof, a sign for 'Brook Bond Tea', and outdoor seating.

19. The Walnut Room - Windmill Country Retreats

The Walnut Room - Windmill Country Retreats
2.0 star property
Melton Mowbray
$370 nightly
The price is $443
Nov 2 - Nov 3
Total with taxes and fees
The Walnut Room - Windmill Country Retreats
A wooden structure with a view of a river and trees.

20. Badger's Burrow

Badger's Burrow
3.0 star property
Oakham
$667 nightly
The price is $800
Oct 18 - Oct 19
Total with taxes and fees
Badger's Burrow
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

The Belmont Hotel

The Belmont Hotel

10/10 Excellent
"We arrived well before our check in time for an event, the reception staff granted us access to the car park for free, which was fantastic. Check in was quick and easy, with a wonderful on site restaurant and bar. Love the high ceilings and comfortable rooms. Facilities in the room were great, with complimentary tea, coffee and cookies. The bathroom also had an array of soaps, shower gel, conditioner and shampoo which was very convenient. We paid for breakfast and ordered the full English which was very tasty, and topped up with a to-go bag with croissants, yogurts and spreads for a mid morning snack. Service was 10/10 with smiling faces and friendly conversation with ladies in the breakfast room. Overall, we had a wonderful stay in a perfectly located hotel to explore the city or stay inside and enjoy a bubble bath. 😍😍😍"
Johnny 1-night trip
Posted 5 hours ago
The Belmont Hotel

Find out more about Uppingham

Uppingham Cottages information

Number of reviews
46
Accommodation
223 Cottages
Lowest Price
$272
Highest Price
$2,460

Frequently asked questions

How much do cottages in Uppingham cost?
Prepare to pay between $272 and $2,460 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 8.9.
How many cottages are there in Uppingham?
Enjoy reconnecting with nature in one of the 223 cottages waiting for you in Uppingham. To help you choose your ideal place, take advantage of our filters to search for must-have amenities.
What are the best cheap cottages in Uppingham?
With cottages starting from $272 per night, you can afford to stay a little longer in Uppingham! One retreat that's easy on your pocket is Wing. It offers useful amenities like individually decorated rooms and a garden. Another cost-effective pick where you can relax and slow the pace down is Tickencote. Individually decorated rooms and a garden are among the conveniences here. Visiting free attractions in Uppingham will stretch your vacation budget even further. Oakham Castle and Rutland Water Country Park are must-do's. With the cash you save, why not explore some more? This price was 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.
Are there any family-friendly cottages in Uppingham?
Spend your family vacay at Ashwell, a 3.5-star cottage just a quick drive from downtown. Amenities here include WiFi and a stovetop. Another family-friendly option where you can swap the concrete jungle for wide open spaces is Cottesmore. WiFi and a patio help make this 3.5-star cottage a guest favorite. Once you've checked in and dropped off your bags, there are plenty of family-friendly attractions to see in and around Uppingham. Oakham Castle and Rutland Water Country Park are two of our top suggestions.
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.

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