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Compare 141 Cottages in Uppingham with updated reviews, rates, and availability.

Gable Cottage
Front of property
Gable Cottage
3.0 star property
9.4 out of 10, Exceptional, (9)
"Perfect spot, close to Oakham. Quiet and comfortable. Friendly host. "
Gable Cottage
2 bedroom accommodation in Easton on the Hill, Stamford
Exterior
2 bedroom accommodation in Easton on the Hill, Stamford
10.0 out of 10, Exceptional, (5)
"The cottage is a lovely period stone cottage , warm and welcoming. Clean and tidy and comfortable. Ideally situated to explore Stamford and surounding towns . Everything you require for a comfortable stay."
2 bedroom accommodation in Easton on the Hill, Stamford
Family and Dog Friendly 3 bedroom holiday Cottage near Oakham & Rutland Water
Property grounds
Family and Dog Friendly 3 bedroom holiday Cottage near Oakham & Rutland Water
10.0 out of 10, Exceptional, (19)
"This is a really lovely property, lots of space with an excellent, very well equiped, kitchen leading on to a big secure garden. we were a three generation family with a dog and the space worked brilliantly. We entertained family and had lots of children visit, the garden toys and sit on tractors where a huge success. I can honestly say we had everything we needed for a very comfortable stay. Jennifer is so helpful and made us feel completely at home, the cottage has lots of nice touches and...
Family and Dog Friendly 3 bedroom holiday Cottage near Oakham & Rutland Water
Beautiful, renovated 1 Bedroom Cottage, with private yard. Great location.
Exterior
Beautiful, renovated 1 Bedroom Cottage, with private yard. Great location.
10.0 out of 10, Exceptional, (2)
"Had a lovely few days/nights here. The property has everything you need for a home from home experience. The cottage is very well located for the town and all of its variety of shops, with frequent buses into Leicester city centre. Thank you for a great stay Rebecca!"
Beautiful, renovated 1 Bedroom Cottage, with private yard. Great location.
Unique house, stylish decor, with garden.
Room
Unique house, stylish decor, with garden.
10.0 out of 10, Exceptional, (1)
"This was a lovely little house. Very nicely decorated, very clean, great facilities and the host has done everything that they can to make you feel welcome. I didn’t know I wanted the hot chocolate but it was very welcome at the end of the day 😃"
Unique house, stylish decor, with garden.
2 bedroom accommodation in Oakham
Living area
2 bedroom accommodation in Oakham
8.0 out of 10, Very Good, (1)
"Spacious, comfortable cottage on a quite road within walking distance of the shops and eateries of Oakham. Rutland Water is a short drive away with its famous Ospreys, the main reason for our visit doWater us a very short drive away"
2 bedroom accommodation in Oakham
Primrose Hall Holiday Cottage, near Rutland Water
Primrose Hall
Primrose Hall Holiday Cottage, near Rutland Water
10.0 out of 10, Exceptional, (35)
"Lovely property in a lovely area. "
Primrose Hall Holiday Cottage, near Rutland Water
Pantiles Cottage in Rutland, the heart of England. Self catering, sleeps 4.
Outdoor dining
Pantiles Cottage in Rutland, the heart of England. Self catering, sleeps 4.
10.0 out of 10, Exceptional, (62)
"Beautifully clean , excelently equipped, beds very comfortable, nice welcome tray and milk in the fridge very thoughtful.. Our arrival was delayed because of a road traffic accident and sadly I didn't have telephone contact details for our host so I couldn't let her know but she was very inderstanding when we arrived."
Pantiles Cottage in Rutland, the heart of England. Self catering, sleeps 4.
Quiet s/c cottage with garden 5 minutes walk to the centre of Uppingham
View of Number Four from the garden
Quiet s/c cottage with garden 5 minutes walk to the centre of Uppingham
9.0 out of 10, Wonderful, (6)
"A brilliant stay at this wonderful property. Hosts are so helpful and have made the property so welcoming to stay in. Easily accessible to beautiful local scenery and everything you need for an amazing stay. "
Quiet s/c cottage with garden 5 minutes walk to the centre of Uppingham
Clicker’s Cottage makes a great base to explore all that Northamptonshire has to offer.
Interior
Clicker’s Cottage makes a great base to explore all that Northamptonshire has to offer.
9.6 out of 10, Exceptional, (5)
"A cosy cottage tastefully furnished and well equipped. Lovely garden. A very relaxing place to stay."
Clicker’s Cottage makes a great base to explore all that Northamptonshire has to offer.
River Nene Cottages
Front of property - evening/night
River Nene Cottages
3.5 star property
10.0 out of 10, Exceptional, (11)
"Thank you for a wonderful stay at Rivernene Cottages. Hosts Stephen and Phil were amazing and could not do enough for all the guests. We stayed in the Yew Tree Cottage, as a family of 4 (2 teenagers) this was perfect! The entire place is immaculately kept. The sweeping garden was a great place to chill out by the bank of the river as well as the delightful heated pool which was used many times during our stay! Cottages are very well equipped with everythjng you could need for a short or...
River Nene Cottages
Yew Lodge
Exterior
Yew Lodge
3.5 star property
10.0 out of 10, Exceptional, (1)
"Its was amazing stay for us"
Yew Lodge
A countryside retreat where you can relax in the hot tub whilst admiring the stunning views.
Exterior
A countryside retreat where you can relax in the hot tub whilst admiring the stunning views.
10.0 out of 10, Exceptional, (1)
"Booked a long weekend for myself and my grown up son to catch up with friends and family who still live in the area We moved North when he was 2 years old and is now in his early 20's so spent the time going to places he went as a baby. The lodge position was perfect as it was quiet but only about 20 minutes from everything. It was cosy and comfortable with everything we needed. My son made good use of the hot tub. are definitely considering booking to do the same next year."
A countryside retreat where you can relax in the hot tub whilst admiring the stunning views.
4 bedroom accommodation in Drayton
Exterior
4 bedroom accommodation in Drayton
10.0 out of 10, Exceptional, (2)
"Great little lodge nestled in the rolling countryside between Drayton and Medbourne. Perfect location for a quiet family break which is surrounded by great walking opportunities and a short drive to the local towns and Rutland waters. Would recommend ⭐️⭐️⭐️⭐️⭐️"
4 bedroom accommodation in Drayton
Church View
Exterior
Church View
3.5 star property
Church View
Think quintessentially English "chocolate box" cottage and you’ll find this is it.
Exterior
Think quintessentially English "chocolate box" cottage and you’ll find this is it.
Think quintessentially English "chocolate box" cottage and you’ll find this is it.
Charming cottage near lovely Stamford with cosy open fire and a rural location.
Exterior
Charming cottage near lovely Stamford with cosy open fire and a rural location.
2.0 out of 10, (1)
"Front door is 5 yards from busy A43. Contacted owner for key code Friday am for Friday stay did not reply till 14.21 Sunday. Builders next door Hammering just after 7 Saturday and Monday. Cover on front bed filthy. Toilet seat not attached correctly. No logs provided for log burner or tools. Welcome pack not as advertised no wine no milk no eggs no crisps small loaf. Outside area no parasols cushions left outside dirty and cigarette burn, and a broken chair. Broken glass in cupboard. Very noisy...
Charming cottage near lovely Stamford with cosy open fire and a rural location.
3 bedroom accommodation in Lubenham, near Market Harborough
Living area
3 bedroom accommodation in Lubenham, near Market Harborough
10.0 out of 10, Exceptional, (1)
"A beautiful, spacious, secluded, property with great country views. Peace and tranquility meant instant relaxation. Just a 2 mile drive to Foxton Locks, and a few miles to Market Harborough. Miles of open countryside which is very rolling, ideal for challenging cycling. My only criticism is that the sound insulation between the two semi detached properties was inadequate. Otherwise marvellous and we will return."
3 bedroom accommodation in Lubenham, near Market Harborough
Willow Lodge
Exterior
Willow Lodge
3.5 star property
Willow Lodge
Farm View House
Exterior
Farm View House
3.5 star property
10.0 out of 10, Exceptional, (1)
"Lovely and quiet at the end of the village. Real home from home. Will definitely be back to stay again in the future. Went out in Leicester so didnt try the The Stilton Cheese Inn which is only a 10 mins walk away & looks good. "
Farm View House
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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Other property types in Uppingham

Quiet s/c cottage with garden 5 minutes walk to the centre of Uppingham
View of Number Four from the garden
Quiet s/c cottage with garden 5 minutes walk to the centre of Uppingham
9.0 out of 10, Wonderful, (6)
"A brilliant stay at this wonderful property. Hosts are so helpful and have made the property so welcoming to stay in. Easily accessible to beautiful local scenery and everything you need for an amazing stay. "
Quiet s/c cottage with garden 5 minutes walk to the centre of Uppingham
The Gresham Aparthotel
Room
The Gresham Aparthotel
3.5 star property
9.0 out of 10, Wonderful, (282)
"We have stayed here before and clearly liked it enough to return. Liked it even better this time. Would wholeheartedly recommend."
The price is AED 337
AED 392 total
includes taxes & fees
10 Nov - 11 Nov
The Gresham Aparthotel
The Hideaway
Terrace/patio
The Hideaway
10.0 out of 10, Exceptional, (12)
"Well-appointed, clean and had everything one would need. Great for a short stay."
The Hideaway
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.

Frequently asked questions

How much do cottages in Uppingham cost?
You can expect to pay between and per night for cottages in Uppingham. No matter your budget, a terrific stay is just 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?
Pick from multiple cottages in Uppingham with a total average guest review rating of 9.2. Amberleigh is a wonderful place to relax and unwind between adventures. This 3.5-star cottage also comes with a garden and individually decorated rooms. The Windmill is another quality option with travelers to the area. It has a 3.5-star rating and amenities including individually decorated rooms and free WiFi.
How many cottages are there in Uppingham?
You can choose from 141 cottages in Uppingham. Whether you’re taking a trip with the kids or planning a retreat with your pals, Expedia will help you find the right space to get back to nature.
Why book your cottage in Uppingham with Expedia?
Expedia has some great cottages in Uppingham, so start packing for an unforgettable vacation on nature’s doorstep. If you’re on a budget, click on how much you’d like to spend and the star rating of your property. Or take advantage of our filters to search for cottages with a pool or free WiFi. We’ll help you find a suitable place whatever your bank balance or plans.
How can I find cheap cottages in Uppingham?
With Expedia’s helpful filter tool, sourcing cheap cottages in Uppingham couldn’t be easier. To discover properties that are very pocket friendly, narrow down your search by amenities, budget and star rating.