Vacation rentals in Uppingham

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Top-rated vacation rentals in Uppingham

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Guest favorite

Cottage in Wing

4.88 out of 5 average rating, 220 reviews

Quiet Rural Chapel Conversion (Architectural Gem)

Stylish & unique, self- contained historic Chapel conversion overlooking stunning scenery, (Chater Valley) tucked away at the edge of Conservation Village, 5 min drive from R.Water. Private. Sleeps 4 1 king-size & 1 small DBL Kids 8+ welcome Park free outside 2 min walk from King's Arms, Award winning Pub. Quiet & very rural. Grade ii Listed. Modern interior feat. in "Living Etc" & won a local design award Helpful owners next door Completely OPEN PLAN INTERNAL WALLS ONLY AROUND BATHROOM

Feb 24 – Mar 3

G$28,070 GYD per night

Guest favorite

Condo in Gretton

4.97 out of 5 average rating, 289 reviews

St James’s Cottage - Gretton

An independent, first floor, apartment in a 200yr old cottage. 1 bedroom available as superking bed or twin beds. Separate living room with kitchenette, combination microwave/oven/grill, single zone hob, toaster, kettle and full size fridge. Bathroom with shower. Free WiFi. Private, off road parking outside cottage. Secure garage space available upon request, for locking up bicycles, fishing tackle, golf clubs etc. Set in a lovely, quiet, village with two pubs & coffee shop in walking distance.

May 1 – 8

G$18,051 GYD per night

Superhost

Home in Rutland

4.8 out of 5 average rating, 141 reviews

Cherry Tree Cottage

Cherry Tree Cottage is a delightful and spacious yet cosy stone barn conversion situated in the peaceful and picturesque Rutland village of Seaton only 2 miles from the historic market town of Uppingham. The property has bi-folding doors opening out onto a completely private enclosed garden. There are beautiful walks exploring the Welland Valley from the property including to the impressive Harringworth viaduct only a mile away. It is the ideal location to explore what Rutland has to offer

Oct 6 – 13

G$20,348 GYD per night

Guest favorite

Cottage in Stoke Albany

5.0 out of 5 average rating, 167 reviews

Converted Barn overlooking fields.

Built in 1634, the Barn is on the edge of a village 5m from Market Harborough in Leicestershire. We converted it in 2017, and it's on our property, but separate from it. Light and airy, it's open plan downstairs, with areas for cooking, dining and relaxing. French doors lead out onto a pretty courtyard garden, with stone steps up to a raised area, where you can watch the sunset over the fields. Upstairs there's a well-equipped bedroom and bathroom with far reaching views over the countryside.

Jul 31 – Aug 7

G$20,972 GYD per night

Superhost

Tiny home in Empingham

4.83 out of 5 average rating, 187 reviews

Lower Farm View - Perfect For 2

Lower Farm View is beautifully converted with outstanding views, it's situated in the Rutland Village of Empingham and is only a short walk from Rutland Water's North Shore. Only 6 miles from the beautiful Georgian town of Stamford and 6/7 miles from the picturesque towns of Uppingham and Oakham. The village itself has a hairdresser, doctor's surgery, shop and pub. The local area has lots of pubs, cafes and shops. A perfect place to be able to enjoy and explore the county of Rutland.

Jun 22 – 29

G$25,324 GYD per night

Guest favorite

Condo in Uppingham

4.92 out of 5 average rating, 118 reviews

Comfy Modern APT - Sleeps 4

Located in the centre of the Historic Market Town of Uppingham. Based in is heart of the small county of Rutland. This apartment is a stones throw away to the gorgeous town centre, with markets every Friday, great places to eat and drink and some really cute little shops. A quick 10 minute drive to another Market Town of Oakham and not far from Rutland Water where you can enjoy some beautiful scenic walks. The apartment offers an allocated parking space and communal paved garden.

Jan 16 – 23

G$21,053 GYD per night

Guest favorite

Apartment in Rutland

4.89 out of 5 average rating, 205 reviews

Clock Cottage Self contained Rutland Rural Retreat

Clock Cottage is a self contained open plan suite located on the ground floor with garden views located within a characterful rural village within a 5 minute drive from Rutland water. The suite is open plan and includes a king sized bed, comfy living area and kitchen, Nespresso coffee machine, freestanding open plan bathtub and separate bathroom and outside dining area. The living area can be used as a family/friends bedroom with the use of a fold out sofa bed. Ideal for couples.

Oct 23 – 30

G$29,442 GYD per night

Guest favorite

Cottage in Wing

4.84 out of 5 average rating, 219 reviews

Idyllic Thatched Country Cottage - a hidden gem!

Situated in the picturesque village of Wing, this adorable thatched cottage is nestled in the grounds of beautiful Cedar House. The property was fully renovated in March 2021 and is the ideal getaway location to explore everything that stunning Rutland has to offer. The cottage is only 5 minute drive to Rutland Water, Uppingham and Oakham, so you have everything you wish to experience during your stay on your doorstep. Historic Stamford is also only 20 mins away.

Dec 1 – 8

G$26,807 GYD per night

Guest favorite

Home in Uppingham

4.93 out of 5 average rating, 105 reviews

36 High Street West -two bedroom luxury terrace

The property is set in the heart of this popular market town opposite the historic Uppingham School. It is perfect for any visitors to the school and is a short walk from the town's amenities which include a good range of independent shops and eating establishments. It is a spacious two bedroom house with a large, beautiful kitchen/ dining space and sheltered walled courtyard garden. The house has been decorated and furnished to a high standard.

Sep 23 – 30

G$31,420 GYD per night

Guest favorite

Townhouse in Rutland

4.95 out of 5 average rating, 249 reviews

Fennel House. Charming house in Oakham town centre

The townhouse is located on a quiet residential one way street. Oakham has stunning historical architecture, i.e a castle, quaint independent shops, pubs and restaurants are moments from the door. A short walk from the railway station. It is ideal for couples or families. A short drive is Rutland Water and is the largest man made lake in Europe 26 miles circumference and hosts many outdoor pursuits such as walking, cycling and bird watching.

Oct 30 – Nov 6

G$31,399 GYD per night

Superhost

Guest suite in Rutland

4.8 out of 5 average rating, 115 reviews

Self-contained Studio annexe in Oakham.

Lovely studio, has its own entrance at the front of house and access to back garden through the patio doors in the room. Recently added a shower in the studio so it is completely self contained now. Small kitchen area with sink and a full size fridge, and a washing machine if needed. There is one double bed in the studio, but also a self inflating single air bed with bedding if required. Smoking is not allowed throughout the property .

Jun 27 – Jul 4

G$16,307 GYD per night

Guest favorite

Home in Manton

4.96 out of 5 average rating, 167 reviews

Oak Tree Annexe

This unique place has a style all of its own, set in a secluded and secure garden. The house is in one of Rutland’s most desirable villages and on the cycle route around the water offering easy access to all the activities that the area offers. The historic towns of Oakham and Uppingham are just a very short drive from the property. The village pub, which serves food, is a 2 minute walk and is very popular with visitors to the area.

Jan 27 – Feb 3

G$27,578 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Uppingham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Uppingham's top sights

Don Paddy's8 locals recommend

The Falcon Hotel3 locals recommend

The Lake Isle10 locals recommend

Scandimania Coffee House4 locals recommend

Goldmark Gallery4 locals recommend

Uppingham School9 locals recommend

Other great vacation rentals in Uppingham

Guest favorite

Barn in Uppingham

4.91 out of 5 average rating, 79 reviews

Topiary Barn - Stylish Accommodation in Rutland

Dec 21 – 28

G$22,564 GYD per night

Guest favorite

Condo in Uppingham

4.85 out of 5 average rating, 20 reviews

Welcome to Sam's Place in Uppingham, Rutland

Dec 13 – 20

G$25,088 GYD per night

Guest favorite

Condo in Uppingham

4.97 out of 5 average rating, 59 reviews

Central Character/Contemporary Apartment

Dec 28 – Jan 4

G$35,496 GYD per night

Guest favorite

Apartment in Uppingham

5.0 out of 5 average rating, 76 reviews

Elegant High Street apartment in Uppingham

Oct 11 – 18

G$29,023 GYD per night

Guest favorite

Townhouse in Uppingham

5.0 out of 5 average rating, 16 reviews

2 Bed house in central location with garden

Feb 12 – 19

G$29,900 GYD per night

Guest favorite

Home in Uppingham

4.98 out of 5 average rating, 42 reviews

Stylish and modern home in Uppingham, Rutland

Nov 7 – 14

G$55,415 GYD per night

Guest favorite

Home in Uppingham

4.98 out of 5 average rating, 42 reviews

Bright modern house in beautiful Uppingham town

Dec 18 – 25

G$30,675 GYD per night

Superhost

Cottage in Caldecott

4.78 out of 5 average rating, 88 reviews

Thatch 1 bed cottage. Period features.

Dec 30 – Jan 6

G$26,844 GYD per night

Show all

Quick stats about vacation rentals in Uppingham

Total rentals
20 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1K reviews
Nightly prices starting at
G$8,358 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Uppingham have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Uppingham. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Uppingham?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Uppingham?
Experience the best of Uppingham with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Uppingham have wifi?
Absolutely! We offer over 10 house rentals with wifi in Uppingham. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Uppingham

Top-rated vacation rentals in Uppingham

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Uppingham vacation rentals

Stay near Uppingham's top sights

Other great vacation rentals in Uppingham

Barn in Uppingham

Condo in Uppingham

Condo in Uppingham

Apartment in Uppingham

Townhouse in Uppingham

Home in Uppingham

Home in Uppingham

Cottage in Caldecott

Quick stats about vacation rentals in Uppingham

Total rentals

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Uppingham have a kitchen?

What are the most popular amenities for House Rentals in Uppingham?

How much does it cost to stay in house rentals in Uppingham?

Do house rentals in Uppingham have wifi?

Destinations to explore