Uppingham Vacation Rentals from $54: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Uppingham?

3 Bed House - Sleeps 6 - Parking - Wifi : This vacation home rental outside of Uppingham comes with free WiFi so you can feel at home during your trip. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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Our top choices for Uppingham vacation rentals

A covered corridor with sliding glass doors leading to a patio area.

1. Relaxing Room With Ensuite Rutland Point

Oakham

jonathan

$69 nightly

Sep 29 - Sep 30

Total with taxes and fees

2. Relaxing Room With Ensuite Rutland Point

Rutland

$82 nightly

Sep 28 - Sep 29

Total with taxes and fees

A wooden cabin with a garage, outdoor seating, and a hot tub.

3. Luxury Shepherd Hut situated on a private 30 acre estate in the heart of Rutland

Ketton

Maxine B.

$200 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

4. 5A Waterfall Way

Market Harborough

Lewis

$351 nightly

Oct 9 - Oct 10

Total with taxes and fees

A bedroom with a bed, bedside tables, a dresser, a television, and a lamp.

5. The Plough, 4 beds, sleeps 9, free parking

Caldecott

$502 nightly

Oct 18 - Oct 19

Total with taxes and fees

A cozy living room with a sofa, teal cushions, a wooden dining table with chairs, a kitchen in the background, and a brick wall with a clock.

6. 2 bedroom accommodation in Oakham

Oakham

Margaret Watters

$302 nightly

Oct 1 - Oct 2

Total with taxes and fees

A dark blue door with a white handle and a decorative glass panel above it.

7. Robin's Nest, your home from home

Wilbarston

"Host there to welcome us when we arrived. He helped to carry in the luggage and showed us how the hot water and heating worked. Amenities were ideal with breakfast food items included plus a bottle of Prosecco and shortbread as a thoughtful Christmas gift. The property had been decorated for Christmas - another kind and thoughtful touch. The property was spotlessly clean and had everything that we needed. The bed was extremely comfortable. Thank you to the hosts. "

Angela W.

$138 nightly

Oct 2 - Oct 3

Total with taxes and fees

8. Double Room with Private Bathroom @ The Gables Aparthotel

Leicester

Stephen

$93 nightly

Sep 29 - Sep 30

Total with taxes and fees

A cozy living room with a fireplace, television, leather armchair, and patterned sofa.

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

bainton

$172 nightly

Sep 28 - Sep 29

Total with taxes and fees

A modern living room with a large window, a sofa, and a dining area.

10. 14 Acres

Market Harborough

$255 nightly

Oct 12 - Oct 13

Total with taxes and fees

A two-story house with a large lawn, a visible garage, and a tree to the right.

11. Relaxing Room With Ensuite Rutland Point

Oakham

Jessica

$69 nightly

Sep 29 - Sep 30

Total with taxes and fees

12. Park View

Leicester

Adam

$45 nightly

Oct 4 - Oct 5

Total with taxes and fees

A modern interior with a dining area, large windows, and a sofa with cushions.

13. NEW Luxury Countryside Retreat for Family and Friends

Clipston

Nic L.

$294 nightly

Sep 28 - Sep 29

Total with taxes and fees

A stone building with a white door, a small window, and a wall-mounted light fixture.

14. Manor View

Oakham

$404 nightly

Oct 2 - Oct 3

Total with taxes and fees

A patio with a grill, outdoor seating, and a view of a field.

15. The Cottage · Luxury Romantic Retreat in Idyllic Rural Location

Clipston

Mashkoor A.

$272 nightly

Oct 5 - Oct 6

Total with taxes and fees

A historic building with a corner turret, large windows, and a sign indicating a bicycle parking zone.

16. The Gresham Aparthotel

Leicester City Centre

Moira

$60 nightly

Oct 25 - Oct 26

Total with taxes and fees

A modern building with a brick facade, solar panels on the roof, and a well-maintained lawn with a pathway.

17. Ascot House

Peterborough

Raquel

$115 nightly

Oct 26 - Oct 27

Total with taxes and fees

A red door with a white window, a brick building with ivy, and a clear sky.

18. 2 bedroom accommodation in Market Overton

Market Overton

Dewyl1

$435 nightly

Oct 5 - Oct 6

Total with taxes and fees

A modern kitchen with blue cabinets, a wooden countertop, and a built-in sink.

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

Stamford, near Easton-on-the-Hill

"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 Â£8 a bag).Bob and Sarah provided a great welcome pack...

Bob Banks

$491 nightly

Oct 4 - Oct 5

Total with taxes and fees

A spacious living area with a stone wall, wooden beams, a brown leather sofa, a television, and a fireplace.

20. Luxury 3 Bedroom Loft Apartment - Central Stamford

Stamford

$457 nightly

Oct 1 - Oct 2

Total with taxes and fees

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Top Uppingham Hotel Reviews

Holiday Inn Leicester by IHG

8/10 Good

"Myself and my partner came to stay on 25th September. We wrote a special request in our booking to be allocated a room far away from the elevator in a quiet part of the corridor. I even phoned in the morning to double check and the morning reception staff assured me that it was sorted. Upon arrival, when we went to our room we discovered that it was directly in front of the elevator which is the complete opposite of what we had asked for. I was not happy but the staff who were on duty in the evening were extremely helpful and pleasant and did the best they could with the limited rooms that were available by that time."

Orton Hall Hotel & Spa

8/10 Good

"The hotel grounds are lovely and it’s a good location but ideally need a car to get to and town. The rooms themselves are a little dated but spacious and comfortable. They were very clean but they are dark and need better lighting. We ate in the restaurant and my meal wasn’t the best but the breakfast was fresh and well stocked. The spa was clean and a nice addition but the men’s changing rooms were not great. The women’s changing rooms would be better with cubicles to change. Staff were friendly and accommodating. Overall a nice stay and would come back."

Delta Hotels by Marriott Peterborough

10/10 Excellent

"On arrival a car with no blue badge was parked in the disabled bay to the right of main entrance. I gave the registration number and showed a picture to the person on the reception desk. He didn’t seem interested and said he thought it was a member of staff and it was obvious he wasn’t going to do anything about it. Unfortunately as a blue badge holder I am finding this becoming an increasingly common approach to managing disabled parking."

The Talbot Hotel, Oundle, Northamptonshire

10/10 Excellent

"A lovely warm welcome when checking in. Brilliant room next to the garden, room nice size with everything you need. All the staff were very friendly and helpful, especially in the bar and the food was very tasty as well. The breakfast nice choice, hot food freshly cooked with plenty of cold breakfast items on offer. A wonderful stay highly recommend. Will be back."

Find out more about Uppingham

Everything you need to know about Uppingham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Uppingham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Uppingham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Uppingham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Uppingham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Uppingham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $54 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Uppingham rentals

At Expedia, we put the best Uppingham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Uppingham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Uppingham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Uppingham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Uppingham?

Yes, we have vacation rentals close to top local attractions in Uppingham, or you can choose a more remote option if you're looking for a relaxing stay. Our travelers say Uppingham has a good selection of bars and the restaurants. Make sure you have time to check out the coffeehouses while you're in the area.

What are some of the best vacation rentals in Uppingham?

3 Bed House - Sleeps 6 - Parking - Wifi: This vacation home rental outside of Uppingham comes with free WiFi so you can feel at home during your trip. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Uppingham?

Expedia has 3 vacation rentals for your stay in Uppingham.

What can I see and do in Uppingham?

Enjoy the area's cultural attractions such as Corby Heritage Centre, or get outdoors into nature at a spot like Rutland Water Nature Reserve. In the larger area, you’ll find Lyddington Bede House and Rutland Water Country Park.

What are vacation rentals like in Uppingham?

Vacation rentals are privately owned properties you can reserve for several days or more in Uppingham. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a family trip.

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Check prices for these dates

Our top choices for Uppingham vacation rentals

1. Relaxing Room With Ensuite Rutland Point

2. Relaxing Room With Ensuite Rutland Point

3. Luxury Shepherd Hut situated on a private 30 acre estate in the heart of Rutland

4. 5A Waterfall Way

5. The Plough, 4 beds, sleeps 9, free parking

6. 2 bedroom accommodation in Oakham

7. Robin's Nest, your home from home

8. Double Room with Private Bathroom @ The Gables Aparthotel

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

10. 14 Acres

11. Relaxing Room With Ensuite Rutland Point

12. Park View

13. NEW Luxury Countryside Retreat for Family and Friends

14. Manor View

15. The Cottage · Luxury Romantic Retreat in Idyllic Rural Location

16. The Gresham Aparthotel

17. Ascot House

18. 2 bedroom accommodation in Market Overton

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

20. Luxury 3 Bedroom Loft Apartment - Central Stamford

Find vacation rentals that suit your style

Top Uppingham Hotel Reviews

Holiday Inn Leicester by IHG

Orton Hall Hotel & Spa

Holiday Inn Express Kettering by IHG

Delta Hotels by Marriott Peterborough

The Belmont Hotel

Rushton Hall Hotel & SPA

Barton Hall Hotel & Spa

The Talbot Hotel, Oundle, Northamptonshire

The Grand Hotel Leicester by The Unlimited Collection

Find out more about Uppingham

Frequently asked questions

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