A church interior with wooden pews, a central aisle, and a stained glass window.

Search Uppingham Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
$358 nightly
The price is $430
Oct 1 - Oct 2
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
$351 nightly
The price is $351
Oct 2 - Oct 3
Total with taxes and fees
2 bedroom accommodation in Oakham
A stone house with a pitched roof, multiple chimneys, and a paved driveway.

3. Historic 200-year old stone built Annex near Stamford, Lincolnshire

Historic 200-year old stone built Annex near Stamford, Lincolnshire
2.0 star property
bainton
$176 nightly
The price is $176
Sep 3 - Sep 4
Total with taxes and fees
Historic 200-year old stone built Annex near Stamford, Lincolnshire
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.
$277 nightly
The price is $277
Sep 9 - Sep 10
Total with taxes and fees
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.

5. 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
$401 nightly
The price is $401
Sep 6 - Sep 7
Total with taxes and fees
2 bedroom accommodation in Market Overton
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
$542 nightly
The price is $542
Oct 3 - Oct 4
Total with taxes and fees
Charming cottage near lovely Stamford with cosy open fire and a rural location.
A small stone building with a tiled roof, a wooden fence, and a paved road.

7. 1 bedroom accommodation in Sproxton

1 bedroom accommodation in Sproxton
Sproxton
10.0 out of 10, Exceptional, (9 reviews)
"A superb little cottage. Couldn't fault it for comfort, facilities and cleanliness. Hosts hospitality was also excellent."
United States
Lynn Hubbard
$518 nightly
The price is $518
Sep 6 - Sep 7
Total with taxes and fees
1 bedroom accommodation in Sproxton
A red brick house with a front door, two windows with shutters, a small porch, and a wooden fence.

8. 3 bedroom accommodation in Melton Mowbray

3 bedroom accommodation in Melton Mowbray
Melton Mowbray
$1,244 nightly
The price is $1,244
Sep 11 - Sep 12
Total with taxes and fees
3 bedroom accommodation in Melton Mowbray
A stone building with a sign reading "THE MALTINGS".

9. Flat 2, The Maltings

Flat 2, The Maltings
3.0 star property
Oakham
10.0 out of 10, Exceptional, (1 review)
"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
$580 nightly
The price is $696
Sep 8 - Sep 9
Total with taxes and fees
Flat 2, The Maltings
A two-story house with a brick facade and a white door.

10. Little Launde Cottage

Little Launde Cottage
2.0 star property
Leicester
$453 nightly
The price is $543
Oct 2 - Oct 3
Total with taxes and fees
Little Launde Cottage
A stone house with a gravel driveway, a small garden, and a wooden deck.

11. 9 Rectory Lane

9 Rectory Lane
3.0 star property
Oakham
$809 nightly
The price is $971
Sep 11 - Sep 12
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.

12. 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
$380 nightly
The price is $456
Oct 2 - Oct 3
Total with taxes and fees
Bumble Bee
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
$577 nightly
The price is $692
Sep 6 - Sep 7
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
$1,020 nightly
The price is $1,224
Sep 9 - Sep 10
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. 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
$680 nightly
The price is $816
Sep 6 - Sep 7
Total with taxes and fees
Squirrel's Nest
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

16. 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
$666 nightly
The price is $800
Sep 6 - Sep 7
Total with taxes and fees
Bee Hive
A patio area with a wooden table and chairs, surrounded by a brick wall and a wooden fence.

17. Stables Cottage

Stables Cottage
3.0 star property
Leicester
$663 nightly
The price is $795
Sep 11 - Sep 12
Total with taxes and fees
Stables Cottage
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

18. Otter's View

Otter's View
3.0 star property
Oakham
$793 nightly
The price is $951
Oct 2 - Oct 3
Total with taxes and fees
Otter's View
A traditional stone building with a sign reading "THE MALTINGS".

19. The Hideout

The Hideout
3.0 star property
Oakham
6.0 out of 10, (1 review)
$562 nightly
The price is $674
Sep 13 - Sep 14
Total with taxes and fees
The Hideout
A row of single-story cabins with a brick pathway leading to the entrance.

20. 27 Brocklehurst

27 Brocklehurst
3.0 star property
Oakham
$431 nightly
The price is $517
Sep 11 - Sep 12
Total with taxes and fees
27 Brocklehurst
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Uppingham Hotel Reviews

Rushton Hall Hotel & SPA

Rushton Hall Hotel & SPA

10/10 Excellent
"."
Mike 1-night trip
Posted 10 hours ago
Rushton Hall Hotel & SPA

Find out more about Uppingham

Uppingham Cottages information

Number of reviews
7
Accommodation
227 Cottages
Lowest Price
$430
Highest Price
$2,509

Frequently asked questions

How much do cottages in Uppingham cost?
Prepare to pay between $430 and $2,509 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 9.0.
How many cottages are there in Uppingham?
Enjoy reconnecting with nature in one of the 227 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 $430 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.

Explore a world of travel with Expedia