Photo by Jules & Jenny (Creative Commons Attribution 2.0)

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

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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
$420 nightly
The price is $503
Dec 13 - Dec 14
Total with taxes and fees
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
$260 nightly
The price is $260
Nov 15 - Nov 16
Total with taxes and fees
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.
$271 nightly
The price is $271
Nov 16 - Nov 17
Total with taxes and fees
The Cottage · Luxury Romantic Retreat in Idyllic Rural Location
Room

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

THE BRIGHT | Exclusive Boutique Residence in the Heart of Stamford
Stamford
$284 nightly
The price is $284
Nov 15 - Nov 16
Total with taxes and fees
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.

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

THE MOODY | Luxury Grade II Listed Retreat in Historic Stamford
Stamford
$284 nightly
The price is $284
Nov 15 - Nov 16
Total with taxes and fees
THE MOODY | Luxury Grade II Listed Retreat in Historic Stamford
A red door with a white window, a brick building with ivy, and a clear sky.

6. 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
$366 nightly
The price is $366
Dec 10 - Dec 11
Total with taxes and fees
2 bedroom accommodation in Market Overton
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 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
$387 nightly
The price is $387
Nov 22 - Nov 23
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.

8. 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
$466 nightly
The price is $466
Nov 15 - Nov 16
Total with taxes and fees
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.

9. 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
$385 nightly
The price is $462
Nov 28 - Nov 29
Total with taxes and fees
5A Waterfall Way
A stone cottage with a red-tiled roof, a green door, and a small garden area with a planter and a pathway.

10. 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
$408 nightly
The price is $490
Nov 21 - Nov 22
Total with taxes and fees
Bumble Bee
A red brick house with a pitched roof, a chimney, and a small porch with a door.

11. Gardeners Cottage

Gardeners Cottage
2.5 star property
Oakham
$2,245 nightly
The price is $2,693
Nov 21 - Nov 22
Total with taxes and fees
Gardeners Cottage
A stone house with a gravel driveway, a small garden, and a wooden deck.

12. 9 Rectory Lane

9 Rectory Lane
3.0 star property
Oakham
$497 nightly
The price is $596
Dec 1 - Dec 2
Total with taxes and fees
9 Rectory Lane
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

13. 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
$684 nightly
The price is $821
Nov 17 - Nov 18
Total with taxes and fees
Bee Hive
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

14. 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
Squirrel's Nest
A patio area with a wooden table and chairs, surrounded by a brick wall and a wooden fence.

15. Stables Cottage

Stables Cottage
3.0 star property
Leicester
$712 nightly
The price is $854
Nov 21 - Nov 22
Total with taxes and fees
Stables Cottage
A stone building with a sign reading "THE MALTINGS".

16. 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
$623 nightly
The price is $747
Dec 5 - Dec 6
Total with taxes and fees
Flat 2, The Maltings
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

17. Rabbit Hole

Rabbit Hole
3.0 star property
Oakham
$1,045 nightly
The price is $1,253
Dec 6 - Dec 7
Total with taxes and fees
Rabbit Hole
A patio with a table and chairs, a brick wall, and a view of a green field.

18. Grooms Cottage

Grooms Cottage
3.0 star property
Leicester
$619 nightly
The price is $743
Nov 28 - Nov 29
Total with taxes and fees
Grooms Cottage
A wooden structure with a circular opening, a bench, and a view of a river and greenery.

19. Otter's View

Otter's View
3.0 star property
Oakham
Otter's View
A traditional stone building with a sign reading "THE MALTINGS".

20. The Hideout

The Hideout
3.0 star property
Oakham
6.0 out of 10, (1 review)
$602 nightly
The price is $722
Dec 5 - Dec 6
Total with taxes and fees
The Hideout
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

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 $260 and $2,693 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.

What are the best cheap cottages in Uppingham?

With cottages starting from $260 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