Vacation rentals in Oakham

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakham

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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

Mar 13 – 20

R2,592 ZAR 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.

Jul 9 – 16

R1,665 ZAR 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

Mar 18 – 25

R1,886 ZAR per night

Guest favorite

Farm stay in Rutland

4.93 out of 5 average rating, 123 reviews

The Old Stables Retreat, Northfield Farm

Quiet, romantic retreat on small family-run working farm w. rare & native breed cattle & sheep. Fascinating place to learn about food & the countryside. Great place to stay & explore one of England's most lovely countryside areas. Farm shop, open for 20 + yrs, sells a wide range of home grown & home butchered meats & local flour, beers, ready meals & pies. Nr. Rutland Water, & Melton Mowbray, of pie fame, Stamford & Leicester. Great pubs abound, as do walks & entertainment of every kind.

Jun 23 – 30

R2,617 ZAR 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.

May 19 – 26

R2,336 ZAR per night

Guest favorite

Cottage in Rutland

4.96 out of 5 average rating, 118 reviews

Beautiful Georgian cottage within a walled garden

This unique family-friendly Georgian cottage, located in the very heart of Oakham. Quiet location, set within a secluded red brick walled garden next to Oakham Castle, and All Saints Church. You will have full use of the property and private garden with summer house, outside seating and dining areas. Facilities include king and double beds, plus a double sofa bed in a second sitting room leading off the main bedroom. Bathroom with shower, kitchen, lounge, dining room & toilet/utility.

Sep 19 – 26

R6,063 ZAR 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 28 – Nov 4

R2,715 ZAR per night

Guest favorite

Condo in Uppingham

4.91 out of 5 average rating, 117 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.

Jun 12 – 19

R1,942 ZAR 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.

Oct 10 – 17

R2,462 ZAR 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 15 – 22

R2,822 ZAR per night

Guest favorite

Townhouse in Rutland

4.95 out of 5 average rating, 248 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

R2,907 ZAR per night

Superhost

Guest suite in Rutland

4.8 out of 5 average rating, 114 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 .

Feb 21 – 28

R1,504 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oakham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Oakham's top sights

Oakham Castle19 locals recommend

Captain Noel Newton5 locals recommend

The Admiral Hornblower16 locals recommend

The Lord Nelson17 locals recommend

Lands' End3 locals recommend

Wheatsheaf3 locals recommend

Other great vacation rentals in Oakham

Guest favorite

Cottage in Empingham

5.0 out of 5 average rating, 116 reviews

Primrose Hall Holiday Cottage Rutland

Feb 22 – Mar 1

R3,233 ZAR per night

Guest favorite

Apartment in Ketton, Stamford, Lincs

4.94 out of 5 average rating, 295 reviews

Private Apartment in the Heart of Ketton, Stamford

Dec 27 – Jan 3

R2,081 ZAR per night

Guest favorite

Apartment in Stamford

4.97 out of 5 average rating, 555 reviews

Stamford Self Contained Flat Private Gated Parking

Oct 1 – 8

R2,015 ZAR per night

Guest favorite

Condo in Rutland

5.0 out of 5 average rating, 34 reviews

Mayfield - 1 bedroom annexe flat

Feb 19 – 26

R2,720 ZAR per night

Guest favorite

Condo in Rutland

4.84 out of 5 average rating, 70 reviews

Comfortable, well located, converted apartment.

Aug 14 – 21

R2,271 ZAR per night

Guest favorite

Townhouse in Rutland

5.0 out of 5 average rating, 52 reviews

Cozy Nook cosy cottage

Aug 19 – 26

R2,477 ZAR per night

Guest favorite

Condo in Braunston

5.0 out of 5 average rating, 12 reviews

Healey House The Annex

Aug 5 – 12

R2,424 ZAR per night

Guest favorite

Apartment in Rutland

4.89 out of 5 average rating, 37 reviews

The Limes - Beautiful Townhouse Apartment, Oakham

Aug 23 – 30

R3,167 ZAR per night

Show all

Quick stats about vacation rentals in Oakham

Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.2K reviews
Nightly prices starting at
R767 ZAR before taxes and fees

Frequently Asked Questions

Do house rentals in Oakham have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Oakham. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Oakham?
Make yourself at home in Oakham by choosing from our most frequently booked neighborhoods. We have over 90 vacation rentals in Braunston-in-Rutland, over 80 vacation rentals in Braunston, and over 80 vacation rentals in Barleythorpe.
Do house rentals in Oakham have free parking?
Absolutely! We offer over 20 house rentals with free parking in Oakham. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Oakham?
Yes! Work meets play with ease at over 20 vacation rentals in Oakham featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Oakham?
Experience the best of Oakham 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.
Are there pet-friendly vacation rentals in Oakham?
Four-legged friends are welcome in Oakham. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Oakham have wifi?
Absolutely! We offer over 20 house rentals with wifi in Oakham. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Oakham?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Oakham

Top-rated vacation rentals in Oakham

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Oakham vacation rentals

Stay near Oakham's top sights

Other great vacation rentals in Oakham

Cottage in Empingham

Apartment in Ketton, Stamford, Lincs

Apartment in Stamford

Condo in Rutland

Condo in Rutland

Townhouse in Rutland

Condo in Braunston

Apartment in Rutland

Quick stats about vacation rentals in Oakham

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Oakham have a kitchen?

Where should I stay in Oakham?

Do house rentals in Oakham have free parking?

Are there vacation rentals with a dedicated workspace in Oakham?

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

Are there pet-friendly vacation rentals in Oakham?

Do house rentals in Oakham have wifi?

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

Destinations to explore